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Can I date my friend's ex?

Posted by Meredith Goldstein  July 14, 2009 10:01 AM

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Hi all. I hope yesterday went OK without me. I had a very nice day off and bought two bottles of the last wine on this page at the Westport Rivers Winery. Nothing like dessert wine.

But enough about my big day off. Let’s get going.

Q: Hey Meredith,

I’m 35 & single. Friends want to set me up w/ 2 different men who dated my girlfriends in the past. I’ve asked around & got very different responses.

Case #1: my college roommate dated “Jason” 16 years ago. I’m still good friends w/ the girl, (she lives in Atlanta, is married w/ 2 kids). In full disclosure, Jason WAS the love of her life -- he broke up w/ her & at the time broke her heart, college ended & they lived far apart. Another friend remained close w/ Jason & now wants to set us up.

Case #2: my friend dated “Bill” 2 years ago for a few months. She blew Bill off for another guy, it didn’t work out & she tried to get Bill back. Bill is single again, she called & he is apparently uninterested. She met bill through MY friend – who now wants to set me up with him. Full disclosure, she says breaking up with Bill was the biggest mistake of her dating life. Also, I have very few single GFs left.

What’s your opinion on being set up with men my friends dated? Can girls stake their claim on guys forever? Do I have to ask permission? Both are good, quality guys – they’re gonna date someone, why not me? Also, if either guy was mean in any way to my friends – I’d never consider dating them. Also, I didn't seek them out.

-- On-the-Fence, Boston

A: OTF, if these relationships had not happened two and 16 years ago, I’d tell you to run from both men to preserve your friendships. But … you’re 35, these guys sound like they have potential, and in one of two cases, your friend has already married someone else.

Here's what I'd do: I’d ask both setter-uppers to orchestrate informal social outings with these men -- group activities, not dates. Feel it out. See if you could actually be interested in these guys. If either of them floats your proverbial boat, I’d approach your friend(s) and tell them what's going on and how you feel. No one wants to see a friend with an ex, but a good friend will want to see you happy.

For the record, I’m more worried about Jason’s ex than Bill’s ex. Even though that relationship happened 16 years ago, the break-up wasn’t up to her and she convinced herself he was the love of her life. In the case of Bill, it was a short-term thing. Your friend blew it, and now she's being overly dramatic about the loss. She barely knew him.

I think it's safe to meet these guys and interact with them. Then, if it's worth it, approach your friends. And brace yourself – you might not get a good initial reaction to “Can I date your ex?” – but if your friends really see the potential for you to be happy, they’ll come around.

Readers? Agree? I’m hesitant about this advice – friends don’t let friends date exes – but in this case, based on age, place in life, and other factors, I think it’s worth some careful exploration. Tell me your thoughts here. Submit a letter to the right. Twitter here.

-- Meredith

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184 comments so far...
  1. I agree with Meredith. These girls should want to see you happy. If they don't, they're either holding a huge torch for the guy or they weren't as good friends as you had hoped.
    Stick with "group dating" for a while before splitting off to one-on-one dating. That way you can keep things casual, without complications, before you're ready to decide which guy you want to focus your energies on.

    Posted by exvermonter July 14, 09 10:22 AM
  1. I'd say you should stay away from the guy that dated your friend 2 years ago. Especially if she says that breaking up with him was the biggest mistake of her dating life. Can't see your friendship lasting long after that.

    I'd say the guy from 16 years ago is fair game. That's very far in the past and I think you give up your stake on a guy when you get married and have kids. I don't think she could come up with any reason to be upset.

    Posted by doubtful July 14, 09 10:22 AM
  1. Hi - I agree with Meredith, again, I thinkyour friend that dated jason, while married, still might have a harder time accepting things. I think you would need to tread carefully there - especially if she has admitted to you that he was the love of her life, it might not be easy to see him happy with one of her good friends, but then again who knows maybe your friends will be fine with it.
    However, you might not even like either of the guys, so wait and meet these guys and see if either one has potential. There are other men out there though and I don't think a man is a good reason to ruin a long term friendship over - unless you see him as the "love of your life" and could potentially marry the guy, otherwise why possibly ruin a good friendship over something that might be tranistory. well good luck

    Posted by JW July 14, 09 10:28 AM
  1. wow this is a boring one.... just date who ever you want. We're all adult. One of your GF's is married and lives in GA! The other guy bill actually might be a good bet. Sounds like he was a keeper that got away.

    Oh and I married my ex's sister... we're all friends now. Sounds weird, but it actually worked out well.

    Posted by anon in cambridge July 14, 09 10:29 AM
  1. Heed Meredith's advice OTF!

    Posted by Amazed July 14, 09 10:39 AM
  1. As a female, I know how hard we girls can be on one another. We hold our girl friends to incredibly high standards and count on them to never do anything to "hurt" our feelings. Both of your friends seem to have lingering feelings for their respective ex. If you don't like your friends that much I say do it! But if you value your friendships with these women and want them around---stay away from exes! Both of them would feel incredibly hurt if you did this. How would you feel if one of your friends dated your ex who you considered the love of your life? The one that got away? Take a walk in their shoes.

    The situation would have been different if you had been friends with these guys over time and realized you may have feelings for them. But you don't know these guys from a hole in the wall. There are 1000's of guys around. Why bother with these 2 when you can find a guy that has no romantic ties to any of your friends?

    The question you need to ask yourself is, is it worth losing friends over? Because by doing it, you are running that risk. I'd say it's not worth it, but that's just me. What do I know!

    Posted by Kathleen July 14, 09 10:46 AM
  1. Both are just too complicated. Just reading the algebraic formula (square root of person A plus person B less 16 years that have past, times breakup C, divided by friend D…) in the letter gave me an ice cream headache.

    In my opinion, LW should weigh her own “Risk vs. Reward” quotient. Perhaps it’s worth it to her to risk friendships or otherwise complicate relationships and potentially create awkward dynamics at future social gatherings, to move ahead with either of these guys. I personally would not, based on my loyalty to friends. I think it’s too risky given that you’ve seemingly never even met either of these guys.

    I would advise you to go your own way. There are plenty of unlinked men out there. Ask your set up friends to not include former boyfriends of the circle of friends.

    FWIW, I’ve grown weary of people assuming mid-30’s is the virtual end of the road for relationships. In this instance, LW being 35 should not create additional urgency that would require getting involved with former “love of life” or other intertwined messes. I think that LW being 35 is irrelevant with regards to the advice required.

    Regarding yesterday's letter, I can relate. The last time I was at a pool party and got my drink on, I ended up getting careless with my drawstring, and my x-factor was on full display after I dove into the pool.

    That’s all the time we’ve got for today.

    - Hoss

    Posted by Hoss July 14, 09 10:48 AM
  1. I was always told about the "cardinal rule" when it comes to dating a friend's ex. The bottom line is, you don't. There are so many quality men out there. There is no need to recycle the ones your friends have already used.

    You'll find someone great who is yours, and has only been yours, good luck.

    Posted by Patriots Gal July 14, 09 10:49 AM
  1. #1 is fair game. The "Statute of Limitations" is only 7 Years after all. And she lives too far away to slash your tires.
    #2 will cause you nothing but grief. Only date him if you want to totally nuke your friendship. OTOH Women are competitive and sublimely hostile, so this could add to the hot drama; which is obviously missing from your life, if you are still playing High School friend-clique dating nonsense at 35 (what's next, tryouts for the Cheerleading Squad?).
    Option #3, buy a Cat and a lifetime supply of Ben & Jerry's...

    Posted by DudeGuyKidDudeGuy666 July 14, 09 10:56 AM
  1. There are millions of guys out there. If there is any risk at all of losing a friend or creating friction between friends over two of them why even bother. There are plenty of other ways to meet people.

    Posted by SJ July 14, 09 10:59 AM
  1. My gut says that the girl who is now married can make no claims. You should be free to date her ex. The only issue is if things get serious, things could get super awkward in the future with your friend. In the second case, you'd be stabbing your friend in the back, since she is trying (or at least hoping) to get him back.

    Still, you have to weigh the risks vs. benefits. As Meredith suggested, I'd try to find out if these guys are worth the risk before even worrying about it.

    For the record, I dated (and married) one of my friend's exes, but I don't think us guys are as possessive about exes.

    Posted by two sheds July 14, 09 11:02 AM
  1. First off, how close are you with these girl friends? Are we talking about Tier 1 friendships or Tier 3? With Tier 1 friends, you should definately ask your friend's if they are okay with it usually. However, I agree with post #2. Your friend lives in GA, is married with 2 kids, and it was 16 years ago, it's history. The one from 2 years ago, tread carefully... I also think your age makes a difference. I am a 25 year old female and I would not date a friend's ex, butttt if I was 35 it would be a different story. Good luck!!

    Posted by clearlyNOTdoingWORKrightNOW July 14, 09 11:02 AM
  1. Good luck - go for it - and if you don't I would

    Posted by Boston July 14, 09 11:02 AM
  1. Men are not pieces of meat! Your girlfriends don't own them. They're people. If those guys wanted to be with your girlfriends, they'd be with them. They aren't, so, they should get over it. Of course, you won't say it to them that way, but know it for yourself.

    You're all also adults... if you were in high school I'd be stepping gingerly around it, but at 35, you shouldn't have to deal with this insecurity.

    It's a small world, you're bound to date people your friends have dated. Meredith's advice to do group dates is fantastic. And when you tell your friends, just state it. "Jane set me up with Jason, small world, huh?" That way you're letting them know what's coming without seeking permission you don't need.

    Posted by sometimes July 14, 09 11:02 AM
  1. Uhm, simple answer, NO!!!
    Seriously, don't your girlfriends mean anything to you? You're 35 and single so you should have some more respect for your girlfriends. They're the ones you're going to need when or if these relationships fail. Doesn't anyone have any loyalty to their friends anymore. If you need help getting set up you should probably set a standard for yourself. "I WILL NOT DATE MY GIRLFRIENDS EX BOYFRIENDS".
    I think you're pretty selfish for considering it. Of all the fish in the sea you need to limit your options to these two?!?! I think you have some more growing up to do.

    Posted by bgcomreader July 14, 09 11:04 AM
  1. I say try it Meredith's way and then see where it goes. Then if it goes somewhere be totally upfront with your girlfriends and say "weird thing, so and so set me up with Jason and after all these years I'm surprised to find I kind of like him that way!" Don't hide it and don't make a big deal about it and be all "would it be okay with you??" and so forth. If one of my friends wanted to date my boyfriend from 16 years ago I'd say "have at it and good luck." Life is weird that way, people should roll with the punches more. You don't get dibs on a guy in perpetuity once it's over.

    Posted by move on July 14, 09 11:09 AM
  1. "Jason" is a no-go, as even though it's been 16 years and she's since remarried, he broke your friend's heart. Even after all this time, it would probably still hurt her to see you with him.

    "Bill", on the other hand, is a green light. Your friend took him for granted, so she gets no say in staking her claim. You can shoot for Bill with a clean conscience, and if she complains, she shouldn't have let him go in the first place.

    Posted by Veritas July 14, 09 11:09 AM
  1. If I ever heard my wife say that some guy she dated 16yrs ago, was the love of her life, well.....those would be hurtful words that would destroy my marriage. What am I second best? But that's not why are writing....I'd say find your own men. You never want these ladies to come sniffing around their old flames. It leaves too much room for "stuff" too happen. There are plenty of men out there and I bet you could find one just as nice as these two guys.

    Posted by SoxSupporter July 14, 09 11:10 AM
  1. I'd say at least Jason is fair game.....probably because I found myself in the same sitch. A good friend dated my now-husband for a couple of years around age 20. About 7 or 8 years later, he and I ran into each other and the rest is history. She took it well and we're all still good friends. She had a great boyfriend then who she's now married to, which I think helps.

    That said, I consciously waited to tell her until I realized we were going to be serious. It did involve some "lies of omission" on my part but I couldn't justify going through what could potentially be hurtful for her for no reason. So I'd hang out with Jason, go on a few dates and see if there's anything there. Hopefully there is, but if not, then you won't have anything to tell.

    Posted by jane July 14, 09 11:10 AM
  1. I have to say I completely disagree! The answer in this case should just be NO! No to both! Even if you ask these girls, there is a good chance they are going to say they are ok with it - even if they are at first, they probably won't be at some point in time. If my best friend asked me if it wasok if she dated my high school boyfriend, the "love of my life", I would say no. It would honestly bother me. Yes, it shouldn't (its been over a decade and I;m happily married now, no feelings towards him whatsoever), but we're human and have emotions, and I wouldn't be comfortable with it. It sounds like both of these girls might also not be comfortable with it (particularly the girl who is still wanting "Bill" back!) If you date these guys, be prepared to have your friendship with these women strained.

    Posted by NOOOOOOO July 14, 09 11:13 AM
  1. Of course, the ideal answer here is don't do it. Never do it.

    But it really depends on how much these friends matter to you, how much your dating their exes would matter to them, and finally, of course, on how much either of these men interests you. If one of them lights you up like a Christmas tree, you've probably got to pursue it. Otherwise, the risk is likely higher than the potential reward.

    Posted by CPThree July 14, 09 11:15 AM
  1. Rico doesn't like cheaters.. Oh sorry. Lost my train of thought. Why risk friendship over two guys? I think you're asking if it's ok because you know deep down inside that it's not. Why get the reputaion of dating your friends ex's? Better yet why don't you ask your two friends if they think it's ok? If your that close to them that you care what they think then you should be able to have an honesty convo about it.. IDK...you have some other motive here that you're not telling us about. There are plenty of men out there so why focus on these two guys. Plus why date some one who it not good enough for your friends.

    Meredith- anybody who refers to themselves in the 3rd person should be banned from making comments.

    Posted by Paul from Wellesley July 14, 09 11:16 AM
  1. For the record. Not all women are insecure and possessive as some of the commenters think. If you were my friend, I'd be first in line to set you up with my ex-boyfriends. Like Meredith said, as a real friend, I'd want you to be happy.

    I should say I don't assume your girlfriends are insecure or possessive either. It's nice of you to be concerned.

    Posted by sometimes July 14, 09 11:20 AM
  1. you should date either one you want. Screw your friend who dumped Bill. Let that be a lesson to all people who think the grass is greener on the other side.

    Posted by peanut4649 July 14, 09 11:21 AM
  1. I didn't get married until I was 36, and I clearly remember the shortage of good men out there. But this is a no-no. Your friends are just that - your friends. You have to hold up your end and not date their ex's. If you pursue this, there will be hurt feelings all around and it's just not worth it. I know it's not fair, but not much in life is. Try your luck with Match.Com or something and forget about these two particular guys. Good Luck!

    Posted by janie July 14, 09 11:21 AM
  1. I completely agree with Hoss - this just sounds too complicated. And I get the vibe that your friends aren't the sort of women who are going to be cool about you dating one of the exes. I also wonder about those trying to fix you up with your friends' exes. It just doesn't seem like a good idea for them to try to fix you up with these guys in the first place. Is there an ulterior motive? Are they also trying to bust up your friendships? Create drama?

    But, if you decide to go for it and ask yiour friends if it's ok to date an ex, just be aware that just because your friend says it's ok doesn't mean it really is. She may think it's ok at the time you ask, or she may say it's ok because she knows she should be ok with it, but deep down inside she might not be. You know your friends better than we do, so ultimately only you can determine if they'd be cool with it or not.

    (And, FWIW, guys can also get upset when their friends date their exes. I know a guy whose former good friend dated his ex. The former good friend is a former good because of it.)

    Posted by Has a bad feeling about this July 14, 09 11:22 AM
  1. Rico's wisdom is to be dispersed to the masses...

    Rico thinks you should look to swim in the rest of the pool...Hanging out by the ladder is not going to get you anywhere. Rico thinks it is a large pool and you should feel free to swim the full length of it and the width of it. The fact you are single at 35 has nothing to do with it being ok or not to date a friends ex. What it tells Rico is that you have a small group of friends and have been closed minded to expanding your social circles. Rico suggests you find some new friends and get yourself out there to meet new people you DON'T ALREADY KNOW.

    You remind Rico of some friends. Rico knows these people that just don't have the open minded personality to think outside the box when dating. They tend to be shallow (not just about physical attributes but education, job, etc...) and stuck with unattainable criteria for their potential mates. Rico has friends that have dated friends ex's in the past and one that actually married a friends ex and lets just say the friendship is not the same as it was. This puts stress on all the friends, not just the ex and the new/old but all the friends since it is weird for all involved.

    This all being said Rico would stay far away from the guy from 16 years ago but the other one he would tell you to consider talkign to the friend first if you decide to go forward. If she is against it then go no further. Rico still feels 100% that you need to get out and be open to meeting other people. Take off the floaties and venture to the deep end, there are some really good fish of all varieties for you to catch. It's ok to catch and release but you need to taste a different fish other than the same minow you've been nibbling on for the past 20 years of dating.

    If Rico were in your shoes he'd be looking for new ways to meet people and giving (as Meredith said yesterday) the shy guy in the corner a chance. Rico has plenty to talk about today if he has time so stay tuned for his updates.

    Love always,


    Is the water really bluer on the other side of the reef?

    Posted by Rico July 14, 09 11:26 AM

    I dont care how long you these old exes have been out of the picture, you do not do a dumb thing like that.

    Learn from me, I did that once to a friend without even asking him, and i almost lost him as a friend forever until he came to grips, i no longer date that person, and hes still my friend.

    If you dont mind being antisocial, never being able to go out for a "ladies night" or just to shop with the girls....then sure go for it....because your going to have a lot of free time when your friends start to hate you. GOOD LUCK!.


    ....i feel like the saw guy.

    Posted by Jigsaw July 14, 09 11:28 AM
  1. I have to say no to dating either of these guys UNLESS it is the ex-girlfriend who wants to set you up. Boyfriends come and go but friends are forever and you should value them. You can't ask them whether they'd mind either because you may not get a straight answer from them. Like the other posters have pointed out there are a lot of single men out there and why risk a lifelong friendship on a dubious fix up? Consider how you will feel the first time you and either Jason or Bill meet up with one of your friends socially. Awkward? It would be a different story if the two women were not emotionally attached to the memories of these guys, but they are. I fixed a friend of mine up with my ex-husband once, after clearing it with both of them. Again, there were no lingering feelings or regrets in my instance. If you can't say the same about your girlfriends, it's best not to risk it. Where is Rico?

    Posted by J Bar July 14, 09 11:34 AM
  1. I disagree with Meredith. I think there are plenty of other fish in the sea, and something smells fishy to me that you would consider dating not just one friend's ex, but TWO. I fear that will look like a pattern to your friends.... and will not reflect well on you.

    Case #1: When was the last time she confided in you that Jason was the love of her life? If it was long ago, then I would have a chat with her. Her feelings may have changed over the years. Maybe they have had contact over the years, and she's come to closure. Perhaps they are in touch daily on Facebook, and she's had a chance to put the break-up into perspective (i.e., she is now thankful that he broke up with her, setting her free to find her husband).

    Or maybe not. I am very happily married and looking back over my own romantic history, there is only one particular ex that I would have a real problem with my friends dating. Yes it was years and years ago. And the reason is simply because that relationship never really had a chance to run its course. In this case, however, nobody broke up with anyone. It was geography that got in the way.

    However there are many past loves in my life that I would have zero problem with my friends dating - and in fact I'd probably try fixing them up myself! Yes I want to see my girlfriends happy - and my exes too. But since we are friends, do me the courtesy of asking me first. Show you care about my feelings, and I will care about yours.

    Feel her out first, before proceeding. If you care about your friendship, get her blessing first. That's what a good friend would do.

    Case #2: Personally, I would not touch this one with a ten-foot pole!!! Why? It sounds to me like Bill and your girlfriend are game-players, and you are about to become their pawn!! Why else would Bill's friend want to fix you up with him, knowing this whole history? Something stinks here. She breaks up with Bill - she wants him back - he wants to date you. Why? To hurt her the way she hurt him??? Probably! Or if Bill isn't the one instigating this through the mutual friend, then it's the mutual friend that likes to see some fireworks. Do you really need this sort of drama in your life? I say NO. There is just something suspicious about this whole scenario.

    Posted by anecdotal evidence July 14, 09 11:34 AM
  1. I wouldn't date either of these guys. In both situations, your friends would be crushed to find out you are now dating their ex. Granted your married friend can't say anything, but that doesnt mean the situation wouldnt bother her/gross her out. You are coming across as desperate by agreeing to be set up like this. If you were all to meet at a group outing and you and Bill/Jason have an instant connection and start dating, that's another story. I'm just worried that both situations could blow up in your face and you'd end up hurt.

    There are 6 billion people on this planet. Your own love of your life is out there. You will meet him when you are supposed to. Have some faith.

    Posted by trueluv4eva July 14, 09 11:34 AM
  1. life is too short - date who ever you want. If the girlfriends get angry, well, too bad. should one of these guys work out, if they were really your friends, then they should be happy for you.

    Posted by linda July 14, 09 11:35 AM
  1. I started dating my best friend's ex 5 months after they broke up. She never spoke to me again. That was 3 years ago and we are still together and hope to get married soon. I hear she is back together with another ex and very happy. Was I sad to lose a close friend? Yes, but it was worth it for me. I am with the love of my life and she got over it and moved on. I say go for it. Both of your situations sound like enough time has passed and it won't be a problem for your friends. I agree with the posters that said that men are not meat and your friends don't own them. Do what feels right.

    Posted by bestthingieverdid July 14, 09 11:37 AM
  1. I used to be of the variety who said date whoever you want, that just because a friend dated someone doesn't mean they are off limits. Then the opposite happened to me.

    I was dating a guy who I was completely in love with. I thought we were going to spend the rest of our lives together. Flash forward a year when he suddenly said he didn't love me any more and left me high and dry. Six months to see him in the bathroom on a Sunday morning after spending the night with my roommate. Three years to their wedding.

    It may seem insignificant, but not only was I betrayed, I took it out on myself - "What does she have that I don't" and was deeply depressed for a year or so. Please, have respect for your friends and yourself and don't.

    Posted by Christine July 14, 09 11:37 AM
  1. Part of me wants to agree with Merideth on this one... but, due to my personal erxperiences, I have to say leave the ex-boyfriends alone. Although I was dating at the time, I tried having a "relationship" with one of my coworkers ex-girlfriend, but it turned out he still thought they were dating. It wasn't more than a week later that I found out he was.seeing my current girlfriend on the side as well.. Needless to say, our work relationship has never been the same -- now he blasts the most terrible music you could ever imagine in our cubicle to get back at me. Trust me, you don't want to be in this position -- if i hear return of the techno remix of "return of the mac" one more time, i'm going to lose it.

    Posted by Street Meat Pete July 14, 09 11:38 AM
  1. OK, the reality is that there are NOT thousands of good men out there, especially when you hit your mid thirties. If you find one, date him. If he happens to be the ex of a friend, that's just the way it goes sometimes. Your friends will get over it, and so will you - and if you won't get over it or can't see yourself having the conversation with your friends, then don't date the ex(es). If the shoe were on the other foot, what would your friends do? The advice provided and to follow is to make sure you want to date these guys first - since, as many women have pointed out already, you may be excoriated and banished from the group. Also know that as you get older, the click of women you associate with will not be as tight, especially as they marry and have children and other issues become more important than whether you are dating one of their exes. Don't worry so much.

    Posted by xz7 July 14, 09 11:39 AM
  1. Oh this is a sticky situation. I am also 35 and agree that it can be very difficult to meet quality men. If I were in your shoes I would definitely meet them like Meredith suggests - casually. If you then ask your friends if it is ok to date them - they will probably say yes it is fine - and then complain about you behind your back (that's what woman do unfortunately). It will sting for them, it will bring back all of the good times they had. It is true that the grass is always greener. They will wonder "what if" and probably feel a twinge of jealousy. I don't care if it's 2 years or 16 years - whether they are single or married with kids - it will still sting!!! With that being said, it is your life and you deserve to be happy. Don't miss out on the chance of meeting your match - just tread carefully. Be open and honest with everyone involved.

    Posted by T July 14, 09 11:39 AM
  1. You should date either one if you want. Yes, the friends might have some emotions stirred up (so be tactful when you let them know). But it sounds like the friends have moved on (whether it was by choice or not, life moves on) and if they're good friends, wouldn't they want you to find the right person??

    I look at it from this angle. I love my friends and want them to be happy. If a friend finds someone to be with, it would feel selfish on my part to obstruct that. It's really my problem if I have feelings about that -- it shouldn't be their problem!

    Posted by Anonymous July 14, 09 11:39 AM
  1. to the people who say there are "plenty of men out there", here's my question... WHERE ARE THEY? I'm 37 & single and I feel your pain! I've done the on-line junk, blind dates, i work in a male-dominated industry, i go out every thurs & fri nights - NOTHING. yes, in a perfect world, it'd be nice not to date men your friends dated - NEWSFLASH - it ain't a perfect world! the friend that's married, has ZERO claim to the guy. The one that broke it off, also ZERO claim. i KNOW how hard it is to find a quality, single guy in this town, if your friends want to set you up with guys that unfortunately dated freinds in the past, GO FOR IT. If they're really your friends, they should want the best for you too. i think the fact that your asking for advice means you've put thought into this & probably don't want to hurt anyone's feelings. good luck.

    Posted by JJ_boston July 14, 09 11:39 AM
  1. I am sick to death of all these people who think you can lay permanent claim to another human being. What about these guys and their right to meet and potentially date someone who from all reports sounds well-suited? As LW tells us, these guys were not jerks to the friends in question (breaking up with someone post-college is not a crime, even if it hurts). Why this continued insistence on exerting post-relationship control over someone else's life? I dated a guy for three years, he dumped me and married his ex. And yet when a good friend of his and I told him we were thinking about dating, he stopped speaking to him. If you like the guy/girl, marry them and live happily ever after. If you decide not to, accept that he/she is free to date anyone they choose, without threat of retribution from you. You had your chance.

    Posted by Q97 July 14, 09 11:39 AM
  1. If I was in that situation, I'd take both friends up on their set ups. It's so hard to meet guys, and here you have two set ups being offered, both with guys you have background info on. I agree with Jane in that you should only tell your respective friend if it gets serious.

    Posted by Erin July 14, 09 11:40 AM
  1. "Can girls stake their claim on guys forever?" I say no. "Do I have to ask permission?" No, you don't need their permission. Having said that, I personally wouldn't do this. There are TONS of guys out there, why do you HAVE TO date your friend's ex's? I've always had a mental block when it comes to my friend's ex's, would never even consider it. On the other hand, I wouldn't care if my friend dated an ex of mine - to me once a relationship is over, it's done and done, BUT I don't think I'd want to hear all about this ex from one of my friends AND I wouldn't want my friend spilling my personal business to an ex of mine, either. If you do it, keep in mind it might be a strain on your friendships with these people. I highly doubt it's worth it.

    Posted by bumbly-bee July 14, 09 11:40 AM
  1. Absolutely, positively do not eliminate either of these guys just because your friends dated them. I agree with Mer - something casual at first to see if you even like them enough to try a date. Then I would go on a very casual date before I mentioned it to my friends. I also agree with "Sometimes" - Men (and women) are not pieces of meat and no one owns them. It is too hard to find someone to love to eliminate people based on former relationships. Everyone has stories about spouses who a friend or sibling dated first. I dated my sister's husband a few times before she did and I never had a problem with them getting together. I met my husband after his friend wooed me all summer with long letters and presents into getting together halfway between where we each lived and he came with his friend at the last minute.

    Posted by JB July 14, 09 11:41 AM
  1. You should date either one if you want. Yes, the friends might have some emotions stirred up (so be tactful when you let them know). But it sounds like the friends have moved on (whether it was by choice or not, life moves on) and if they're good friends, wouldn't they want you to find the right person??

    I look at it from this angle. I love my friends and want them to be happy. If a friend finds someone to be with, it would feel selfish on my part to obstruct that. It's really my problem if I have feelings about that -- it shouldn't be their problem! I fully know that feelings of longing, loss, regret, guilt are part of the deal when it comes to the business of love. If you and you're friends are open and honest about your feelings, and approach things with love and respect, you'll be just fine!

    Posted by Living life with love and color July 14, 09 11:42 AM
  1. Whatever you decide to do, that is the kind of friend you are.

    Posted by WhetDreamz July 14, 09 11:45 AM
  1. I think that if you're 35 and still single, there's not a huge chance you're going to like either of these guys anyway. I don't go for the "group date" advice. That's really weird, like you're parading the guys in front of you for you to choose. I wouldn't want to be one of those guys, and I don't think anyone with decent manners would agree to it. If you're interested, just have your matchmaker set up an informal meeting in a coffee shop or wine bar and go from there. A married woman with 2 kids shouldn't give a rat's petooti about somebody she dated 16 years ago, "broken heart" or not. Have some dignity, people. The other friend who blew her guy off deserves not to have him. Where's the problem?

    Posted by baroque July 14, 09 11:46 AM
  1. Here is another perspective: I, personally, would love it if one of my single friends dated one of my good ex-boyfriends. Part of the reason I feel that way is that most of my exes were close-but-not-quite matches for me, and my friends are a LOT like me. It seems like the perfect way to find someone, actually. Granted, I come from the perspective of a married woman, so I am not "on the market" but I honestly think once we got over the hurt of a failed "could have been" either one of us would have been happy to see the other with a good person.
    I highly encourage the "group activity" agenda, btw. It is less pressure and you get to see someone in action, not necessarilly on their best first-date behavior!

    Posted by merilisa July 14, 09 11:48 AM
  1. I don't think there is one right answer here.. But my feelings are the opposite of Meredith's.. If these girls are really your friends, then I would tell them right from the front that someone wants to set you up and ask if they mind... If they don't mind, great.. If they do mind, then you'd have to decide whether your friendship is more important than going on a date that may or may not lead anywhere.. But I think it's better to do this before you see the guys than after..
    As for Bill or Jason, I'd be more worried about Bill's ex than Jason's, as that was only 2 years ago, and you KNOW she is still interested.. If Jason's ex is still not over him 16 years later, after she is married and has kids, then she has serious problems and probably needs therapy.

    Posted by Tom July 14, 09 11:50 AM
  1. Never, ever, ever, ever, ever date a friend's ex, no matter how it ended, who ended it and how long ago it was.

    In a world of 6.7 billion people, you don't do this type of thing.

    Posted by sluggosan July 14, 09 11:51 AM
  1. The fact that you have to ask this question should give you your answer. Stay away from both.

    Posted by Common sense July 14, 09 11:52 AM
  1. So many people wonder why risk it? I will tell you why: A friend is not someone who is going to live with you and provide you companionship the same way a spouse is. I have plenty of friends, none of whom live anywhere near me anymore, so if it weren't for my spouse, who would be there for me? And exactly who would be there by my side, buying a house with me, seeking out good used cars, feeding the pets, raising the KIDS (hello???) ...? Friends mean a lot, but they do not mean EVERYTHING, and a friend who is going to stand in the way of a serious romantic relationship is not a friend who has your best interests at heart. My view: If a friend is married, they have no claim on an ex. If a friend has broken up with someone, they have no claim on them anymore. That doesn't mean they won't be unhappy. They will. But if you follow the "try an informal trial first" rule of thumb, you should be able to avoid unnecessary friction. You can go to informal gatherings just to see if you'd be interested at all. If it looks like it's has gotten really, really serious, like spend the rest of your life with him serious, then talk to your girlfriends. I am not a proponent of asking permission. I think that's giving too much power to someone else. And it's YOUR life.

    Posted by AlicePalace July 14, 09 11:53 AM
  1. I disagree with those who think this is complicated - I don't find this complicated at all. Men from the past have resurfaced. Now they're available when OTF is available. This is not rocket science.

    In fact, I'd argue that this is quite common. Friends tend to have similar tastes, so it's unsurprising a guy would "circulate" within a group, so to speak.

    These exes are in the past of both women. The simplistic "friends first" ideal that others on the board are citing is just that - far too simplistic for real life. Taking into account maturity, life situations, and specifics, I'd move forward with Meredith's advice. After all, getting what you want (which in this case is a relationship) often requires breaking a few rules of convention.

    Posted by Fievel July 14, 09 11:53 AM
  1. I am a girl, so I can say this with total confidence. If you approached me and wanted to date MY "One that Got Away", I would feel like a real jerk if I said, "no" because I get that I don't own the rights to him forever. BUT, and it's an important BUT, hanging out with you and MY EX-FISH would be hard and time would either drive me away or allow me to get over it -- never know which way it would go though. You willing to risk that? (not with me; with your friends)

    Posted by puttytat July 14, 09 11:54 AM
  1. I'm sure there's input out there that is 5 paragraphs in length and long winded blabbering is not necessary ,so lets keep it simple and to the point.
    I don't understand the need for permission - why the insecurity?
    Everyone is single "mature" adults with no "current" strings attached. There's too much drama being supplied by you... Just go out on a couple of dates already

    Posted by twocents July 14, 09 11:55 AM
  1. Date who you want and don't ask permission. If you let them control who you date, they will always be in the middle of your relationship.

    Posted by Sabs July 14, 09 11:56 AM
  1. I wouldn't be upset if my friend dated an ex, but then again, I've never really been in that situation before (since high school)....I guess I'm not too sensitive about that stuff(?) An ex is an ex for a reason after all.....

    However, I would never, NEVER date a good friend's ex, unless the friend had a really casual relationship with the guy and my friend had clearly moved on. I have found that although good guys are hard to find, good friends can be even harder to find. I believe one can live without a signifigant other, but not without good friends.

    Do you know what your college roommate would do if she were you? How good of a friend is she?

    I am 27, so I don't know what dating at 35 for women in Boston is like, but I get the impression that its pretty tough. Both my roommate and I have boyfriends in their mid to late thirties, and most of my girlfriends who are in their thirties are still single, so that may say something about the availibility of quality single men in Boston.

    That being said, I think Meredith's advice is great. See if either of these guys is even worth starting something special with, then cross that bridge when you get there. Good friends usually do get over stuff.

    I'm curious, did you and "Jason" go to college in Cambridge?

    Posted by Tricia July 14, 09 11:59 AM
  1. ask the friend (now former friend) if it is okay...

    it won't be.

    Posted by sarah July 14, 09 12:02 PM
  1. A guys view:

    The guy from 16 years ago is a definite no, if your friend is a "tier 1" friend. The guy broke her heart. Unless she's over it you'll be breaking the line of solidarity. I know I was ticked at my best friend when he told me about run-ins with my ex from a particularly bad breakup. And he wasn't looking to hook up with her. I didn't care if he talked to her, I just didn't want to hear about it.

    I say the 2 years ago guy is fair game. She screwed up. She's fooling herself if she thinks the guy will come around. I certainly wouldn't be interested in a girl who had left me to go chase after someone else. She flubbed her chance, he brushed off her subsequent advances, he's open season. I reccommend following Merediths advice for starting it up, but its definitely not an "absolutely not"

    Posted by married in nh July 14, 09 12:03 PM
  1. I think you should go for it, heeding Meredith's advice. Be prepared for the worst case scenario with the friends. You can never predict how people are going to react, and no matter what we say here, it will be awkward or hard for them, esp. right away!

    You have to live your life....and you only get one.

    Posted by Ava July 14, 09 12:08 PM
  1. 1. Stop with the "me first, too bad for anyone else" nonsense. I don't buy the argument that there are no good men out there in the 35 year old age range, so she should poach or otherwise complicate your potential relationships out of dire necessity.

    2. No one said she needed to "ask permission", however, these women are her FRIENDS currently, so as a sign of respect, one would think you would want to get their feedback on the situation.

    3. I love it when Rico reads other comments and then tries to steal bits and pieces of them in his own thoughts.

    4. Enough with the pool / fish analogies.

    5. To anyone who is lonely or is wondering where potential dates are, I would like to inform you that they will not drop out of the sky and land next to you on your couch while you watch the latest reality show du jour. Turn off your tv. Leave your house. Get out and get into social situations.

    6. If you are a proponent of LW risking one or two friendships to date men she's never met or seen before, then as another commentor pointed out, it says a lot about the kind of friend you really are.

    Posted by Hadie Nuff July 14, 09 12:13 PM
  1. Re: #54: "I'm sure there's input out there that is 5 paragraphs in length and long winded blabbering..."

    Yes. It starts with the usual nauseating pomposity, "Rico's wisdom is to be dispersed to the masses..."

    Posted by Truman July 14, 09 12:13 PM
  1. Too many logistics. I'm with Rico; just move to a deeper part of the ocean. It's tough, but worth it.

    I have the same issues with dating as the LW, so I feel her pain, but you have to ask yourself if it's worth blowing a friendship over a short relationship. If there's long-term potential, then you might want to reconsider, but tread lightly. Relationships are hard to come by, but friends are even harder, especially as you get older.

    One more thing to ponder: what's wrong with these guys? The one who broke your friend's heart might have grown up a bit (I hope), but he still really hurt her. As for the other guy, your friend blew him off. Maybe she picked up on something? She might regret it b/c the other relationship she pursued didn't work out, but she did have her reasons at the time.

    Like I said, too many variables.

    Posted by P&P July 14, 09 12:13 PM
  1. There is always drama about dating friend's exes or dating an ex's friend or whatever - the thing is they are probably great people to date. Friends tend to be friends because they share common values, have similar sense of humor, enjoy the same activities, etc. That usually means that the people your friends dated or the friends of people you dated could be good fits for you (not always but sometimes).

    In general I think people should be allowed 1 don't-go-there ex (or longed for but never dated guy). I mean I have no interest in currently dating the guy I crushed on all through high school. We had flirtations but never dated. I'd still be upset if one of my friends dated him. I know it sounds petty but that's just the way I'd feel - I know it's irrational. I hope he finds happiness with anyone who isn't my friend.

    That said, maybe you should hang out with them casually first and see if there is even any mutual interest. Then I would ask your friends. While I think they shouldn't say no - everyone is different and it shows that you are considering their feelings. The married friend might carry a little torch for him still but probably realizes that she's married with kids (and hopefully happy). The other still single friend might meet someone next week and then be totally over that other guy (or not). It's the sort of thing you'll laugh about 10 years down the road.

    Posted by pomgreen July 14, 09 12:14 PM
  1. ummmm #50, AlicePalace: I think you've got this all flipped. A friend who dates an ex knowing the pain and suffering a break up has caused does not have the friends best interests at heart. Maybe this is why you have no friends?

    Posted by Christine July 14, 09 12:14 PM
  1. Case #3: "Bobby" held hands with my friend "Susie" during sex-ed class, the one where "Mr. Woodcock" showed us how to put a profolactic on a banana, but then "Bobby" got caught necking with some ho we'll call "Sally" under the bleachers and knocked her up. Now "Bobby's" out of prison, "Sally's" on the dole, and "Susie" is a lesbian. May I date "Bobby?" Or should I date "Susie"?

    Social retardation is a bummer. I think we should all refer back to that letter from the girl who didn't have female friends...

    Posted by Sally July 14, 09 12:15 PM
  1. My gut reaction from the headline was - NO WAY!

    I then read the letter and Meredith's advice. I think Meredith has a great idea and you should follow it.

    Posted by JustForComments July 14, 09 12:16 PM
  1. Sounds like the writer went to Harvard or some other snotty school...BC? Bentley, Babson? etc... Seems to be a normal thing for those people at these types of schools to only date only those in their little circle. You could have gotten that education at the library for a few bucks in late charges and saved over $100k.

    35 still thinking of dating friends ex's...you are going to be a lonely wretched old woman alone with your cats and a fancy diploma.

    Posted by Joshua July 14, 09 12:16 PM
  1. Since you are posting on this site and bringing attention to yourself, you clearly have a flare for drama. I advise both guys to run fast and far.

    Posted by runfastrunfar July 14, 09 12:18 PM
  1. I married my ex's best friend. My husband asked my ex if it was ok to ask me out before anything happened. Less than 9 months later we were engaged and have been married for 6 years Life happens. Get your date on.

    Posted by IMHO July 14, 09 12:18 PM
  1. As someone who has discussed similar situations with friends, I would agree with Meredith's advice. While people should not feel as though they can "claim" other people as their own, I do feel that everyone is entitled to one guy (or girl) who is off-limits to friends for dating. Usually this person is a first love, or a first significant relationship...it sounds like Jason may be that person for OTF's friend. Bill sounds like a better option (in terms of friend politics).

    Posted by LL July 14, 09 12:21 PM
  1. There is an unwritten rule here....you NEVER date someone that dated one of your friends. NO WAY

    Posted by Deb July 14, 09 12:25 PM
  1. Simple answer: Yes and yes. Totally ok.
    She dated one guy 2 years ago for a few months and dumped him!? That's not an "ex" - that's a cup of coffee. (And kudos to the guy for having enough self-respect not to get back together with her.)
    And as for the post-16 years guy, are you serious? He's completely fair game. Concern generally on this topic only should begin if the guy/girl was someone's fiance(e) at the least, in my opinion.

    Posted by Bob July 14, 09 12:26 PM
  1. AlicePalace.. if you ever lose your husband, you will realize how important girlfriends are. I'm in my 50s.. talk about good men being scarce... still wouldn't do it!

    Posted by Linda July 14, 09 12:26 PM
  1. I'm currently working on a soon-to-be best seller:

    "Men Are From Mars, Women Are Mental".

    Posted by Raymond Cist July 14, 09 12:28 PM
  1. "She met bill through MY friend"
    I have to laugh at this qualification - what difference WHOSE friend it was? Are you that controlling? Never should this become a justification tool.

    The married one should remain focused on the man she is married to and while it may sting at the thought of 'anyone' being with the love of her life it really doesn't matter who that would be. So, I'd be up front with her and tell her that you'll be dating her ex. Her ex is old news and a closed chapter - nothing will change his being her ex - with or without your dating him.

    The other friend - she gave him up and now he is free for other opportunities including you. It wasn't love (2 months dating) and she blew him off for someone else and it was 2 years ago. She's in a dating slump and reflects on how she let a decent guy go. I agree with Meredith - overly dramatic and it makes no sense.

    In either situation, I can't see how either of your girlfreinds could justify putting a 'hands off' sign on him. They may not like it initially, but if you get a relationship from it with either guy, they'll eventually warm up to the idea.

    Posted by marj July 14, 09 12:28 PM
  1. Who cares if you're 35? The love of her life? Don't touch that one. I would be devastated if one of my good friends went after the love of my life, even after many years. Any other guy should be fair game though.

    And Joshua, don't go around passing off lines from a movie as your own original thinking. Lame.

    Posted by OntheDeck July 14, 09 12:32 PM
  1. Yanno, I feel sorry for the 2 men in this situation, not the 3 women. Here they are, being debated and passed around. Don't they get a say in all this? How do they feel about the 2 and 16 years that have passed? Do they get permission to give or reject, too? Some of you are treating them like unfeeling objects. And I hope the L/W, if she decides to see them, has her letter-conversation with them. Otherwise (and this statement is for Mistral), the men may end up being Camille Claudel to Auguste Rodin.

    Posted by reindeergirl July 14, 09 12:39 PM
  1. Joshua-

    Even though I went to one of the schools that you mentioned, I totally agree with you. Maybe the best post ever. I love single 35 y/o women who complain about the lack of quality guys!! I think they should look in the mirror!! More than likely a “quality guy" doesn't look at you as a "quality girl". When a guy looks at a single 35y/o the first question that comes to mind is, what's wrong with her? Instead of trying to date an investment banker who participates in triathlons on the weekend maybe you should set your sights a little lower (i.e.).. A garbage man or a high school janitor.. Maybe that is more in line with your level??

    BTW, if Meredith is still single when she is 35 then it won’t have anything to do with the above. It just that so many guys like her that she is having a hard time picking one out!!

    Posted by Paul from Wellesley July 14, 09 12:49 PM
  1. The only thing constant is change. Let go of former loves.

    That said, has anyone seen my high school sweetheart from 30 plus years ago? Boy she was kind and smart and pretty......

    Posted by cisco kid July 14, 09 12:50 PM
  1. The only thing constant is change. Let go of former loves.

    That said, has anyone seen my high school sweetheart from 30 plus years ago? Boy she was kind and smart and pretty......

    Posted by cisco kid July 14, 09 12:50 PM
  1. The only thing constant is change. Let go of former loves.

    That said, has anyone seen my high school sweetheart from 30 plus years ago? Boy she was kind and smart and pretty......

    Posted by cisco kid July 14, 09 12:50 PM
  1. The only thing constant is change. Let go of former loves.

    That said, has anyone seen my high school sweetheart from 30 plus years ago? Boy she was kind and smart and pretty......

    Posted by cisco kid July 14, 09 12:51 PM
  1. Joshua-

    Even though I went to one of the schools that you mentioned, I totally agree with you. Maybe the best post ever. I love single 35 y/o women who complain about the lack of quality guys!! I think they should look in the mirror!! More than likely a “quality guy" doesn't look at you as a "quality girl". When a guy looks at a single 35y/o the first question that comes to mind is, what's wrong with her? Instead of trying to date an investment banker who participates in triathlons on the weekend maybe you should set your sights a little lower (i.e.).. A garbage man or a high school janitor.. Maybe that is more in line with your level??

    BTW, if Meredith is still single when she is 35 then it won’t have anything to do with the above. It just that so many guys like her that she is having a hard time picking one out!!

    Posted by Paul from Wellesley July 14, 09 12:52 PM
  1. #1 - Yes
    #2 - No


    Posted by DrK July 14, 09 12:53 PM
  1. a teir two friend of mine got together with my ex shortly after we broke up (full disclosure - i broke up with him), and truthfully i couldn't be more happy about it. what's better than seeing two people that you really care about fully in love, and happy? imho it makes total sense that your friends might be into your ex's... after all you were into your ex once too.

    Posted by bostonistoosmallfordating July 14, 09 12:54 PM
  1. are your 2 girlfriends still friends with the friends whom are close to their exes?

    I say dont do it. A friend stayed friendly with my ex and it has hurt our friendship. It will never be the same.

    Posted by me July 14, 09 12:56 PM
  1. Joshua-

    Even though I went to one of the schools that you mentioned, I totally agree with you. Maybe the best post ever. I love single 35 y/o women who complain about the lack of quality guys!! I think they should look in the mirror!! More than likely a “quality guy" doesn't look at you as a "quality girl". When a guy looks at a single 35y/o the first question that comes to mind is, what's wrong with her? Instead of trying to date an investment banker who participates in triathlons on the weekend maybe you should set your sights a little lower (i.e.).. A garbage man or a high school janitor.. Maybe that is more in line with your level??

    BTW, if Meredith is still single when she is 35 then it won’t have anything to do with the above. It just that so many guys like her that she is having a hard time picking one out!!

    Posted by Paul from Wellesley July 14, 09 12:57 PM
  1. Please... If someone else wants to set you up then let them. Forget this walking on eggshells around the friends. They really shouldn't care. They realized these guys had potential and blew it. Life's too short for you to be sitting there alone on Saturday night wondering "what if...". People meet people in so many weird ways. Life's funny that way. And besides, what's more important? Your happiness or the feelings of your friends? There are NOT a ton of potential good mates out there so don't turn your back on a chance that might end up good. Be selfish. And I agree that however they react is a good sign of what kind of friend they are.

    Posted by Been There July 14, 09 01:05 PM
  1. my advice is to tell your two friends that people want to set you up w the two ex's. See what their reactions are and tell them you don't want to do anything to harm your friendship(s). I did this w my oldest friend from first grade and she said she had no problem w it but it later turned out she did but would never say so. Since I valued her friendship, my loyalties were w her and I didn't date the guy. I care too much about my friend to do anything that would hurt her. If all depends on how close your are w your two friends. Are either of these guys worth it?

    Posted by Rosie July 14, 09 01:09 PM
  1. So, my question is... If these guys dated your friends (one you claim to be a good friend), wouldn't you have some idea as to whether or not you are attracted to them and if there may be potential for a relationship with them? If you forsee any potential with these guys, is it enough to warrant risking your friendships? Again, since these are friends of yours, can you guess how they would respond to hearing you are dating Jason or Bill? I don't believe in the hard and fast rule that you shouldn't date an ex, as there are just too many reasons why it could work out, but in these situations, you aren't going in blindly. You should have enough information to be able to make the decision on your own.

    Posted by k July 14, 09 01:12 PM
  1. Follow your heart and do what makes YOU happy.

    Posted by MTM July 14, 09 01:16 PM
  1. A little surprised at the vehemence with which (mostly women, it seems) are saying to stay away from these men. My initial thought was, they are all grownups, and in either of those situations I can't imagine any one of my friends protesting. And that's why I liked Meredith's advice, because it ensures OTF is not investing too much into the possibility, leading to needless trouble.
    But I think just by asking this question OTF is uncovering the potential for one or both of these situations to turn into very bad things.

    Posted by heartseek July 14, 09 01:18 PM
  1. I am really shocked by the people advising NOT to date these guys? Are you kidding me? Oh that's right - we live in overly sensitive Massachusetts, where someone who has no right to claim an emotional attachment to a past lover *might* get their feelings hurt. PUH-LEEZE! All of you really need to get over yourselves.

    Posted by Bob July 14, 09 01:24 PM
  1. Wow. Coming from someone who married the love-of her-life, I think it would be so sad if your friend really held a torch for Jason, 16 years later. That said, some women are really unreasonable about this kind of thing. (obviously, because some of them have posted here.) In college, I dated a guy that my friend had previously "hooked-up" with, one night. She didn't speak to me for a whole year!!!! It didn't end the friendship, but did put it on hold for a while. Of course, as it turns out, she wasn't such a good friend. A few years later, she did something really awful that did end the friendship.
    I say, take Meredith's advise. Have a meet and greet with each. Maybe there will be no chemistry and nothing to ruin a friendship for. But you may always wonder if you don't at least meet them.

    Posted by betty July 14, 09 01:25 PM
  1. Ok. This happened to me eleven years ago when I got together with my now husband. He had dated my good friend seven years prior when they were in high school. I did not plan to get together with him it just sort of happened and we fell in love. At the time she was and had been dating her now husband for quite some time.
    To be honest with you, I did tell her, and our friendship has not been the same since but would I do it all over again the same? You bet.
    People drift apart regardless and as I read in another post, your friend is not going to live with you and be your constant companion.
    I questioned myself in the beginning of the relationship because of their history but I decided that she was happy with someone else so why shouldn't I be happy as well.
    Good luck.

    Posted by afriend July 14, 09 01:28 PM
  1. On the one hand, it seems like dating either guy is likely to lead to hurt feelings and drama. For that reason, were I in your shoes, I would probably look elsewhere. But, thinking more abstractly, neither of these women (especially number 2, who sounds like a drama queen with her statement that breaking up with Bill after dating for a few months was the biggest mistake of her dating life. The time and place for such hyperbole is high school; not adult dating) can lay claim to these guys.

    I like the idea of meeting both of the men out in group situations as a way to gauge chemistry. If sparks with either of them, discuss the situation with the respective women. It is hard for me to fathom your married friend being angry with you as Jason is far in her past. If she is angry, that is an issue that she and her husband need to work out. As an aside, the notion of a married woman clinging so tightly to a college ex is disturbing. And we wonder why the divorce rate is so high. It sounds like the second lady will be upset; I am guessing you have dealt with her dramatics in the past and therefore have more insight into handling that than I do.

    Posted by fairlee76 July 14, 09 01:29 PM
  1. Someone who would want you to miss out on potential happiness because she can't get over an ex is not a real friend. A real friend cares more about you than their own foolish pride & old baggage. If either one has an issue with this, you're better off without them.

    Posted by Q97 July 14, 09 01:29 PM
  1. Yes and Yes. Meridith nailed the best way to proceed...

    Posted by Darwin July 14, 09 01:29 PM
  1. OTF - I think the fact that you even wrote to Meredith is a good sign that these women are close friends of yours. I was once the gal whose best friend dated my ex. It was a mutual breakup but it had only been a couple months when my best friend asked if she could date him. I wanted to scream “NO!” but I figured that if she liked him and he liked her, it was none of my business. Eventually she realized he wasn’t worth the trouble but she and I are still best friends.

    I’ll admit, at the time it felt like I was being betrayed but given the time frame you’re dealing with and the respect you have that you’d ask first – I think your friends will be happy for you if you and Bill or Jason make it as a couple.

    One last thing – seeing my friend with my ex only made me realize how happy I was that I wasn’t the one with him anymore. I think that maybe once your friends see these guys with you, they may realize that they’re happier where they are now. Really though – don’t stress it. Meredith gave awesome advice.

    Posted by That Friend July 14, 09 01:31 PM
  1. I'm tired of this "it shows what kind of friend you are" stuff. How selfish is it to say, I'd rather have you remain single, while I'm happily married, than have you date someone who didn't like me? And, what about the MEN in these situations? Is it really OK for them to be held hostage by two women from the past?

    I'm married to an ex's best friend. Was I not supposed to fall in love with the love of MY life because i went on a few dates with someone else?

    I would test out whether you actually LIKE either of these guys first, and then talk with your friends abuot it. I think their response shows what kind of friend THEY are.

    Posted by catherine July 14, 09 01:34 PM
  1. 1. There is NOT a million good fish in the sea in your mid-thirties. I know, I'm still fishing.
    2. Do the casual meet and greet, see if you are interested in either or both.
    3. If you do start dating, wait until it goes from casual dating to more exclusive before you broach the subject with either friend.

    No use in putting it out there until there is something to tell them about.

    Posted by LuluLemon July 14, 09 01:37 PM
  1. On the fence: here's what you do - set up a little menage with each GF and their ex. Have a little wine, a little weed, and enjoy yourselves. Then let each man choose his favorite: his ex GF or you. Problem solved.

    Plus, you get a little extra excitement in your life. AND you get to lord this adventure over your married friends, reminding them once again that as a single babe you can still have these kind of adventures while they are stuck with their humdrum suburban minivan-driving soccer-attending existences.

    Posted by Don Juan Lynn July 14, 09 01:39 PM
  1. It depends. Did your friends get buggies from those guys?

    Posted by fzappa July 14, 09 01:50 PM
  1. It depends. Did your friends get buggies from those guys?

    Posted by fzappa July 14, 09 01:51 PM
  1. As usual, I agree with Meredith's response...don't rule it out, but tread lightly. Curious why you asked if you "HAVE TO" ask permission? In life, no one really HAS TO do anything, but also in life, there are consequences (both intended and unintended), so the question really is...what are willing to proceed with and possibly either gain (perhaps a wonderful boyfriend or dating partner) or give up (possibly hurt feelings from a girlfriend). Neither is guaranteed. For all you know, either guy won't be a good fit for you and/or both girlfriend's don't give a flying you-know-what if you date them. But then again...life isn't about guarantees or die-hard dating rules. You didn't mention if you've met either of them before, but regardless, I like the group hang-out option to see if there's anything chemistry-wise worth pursuing. Doesn't make sense to ask for permission or get feedback from your friends, find out you're not that into them, but now because you floated the idea, their antenae is up for good. If you make a connection with one of them, I do think they should hear it from you as soon as possible so it's not spread through the grapevine....something along the lines of...."just so you know, me and happened to meet up and I'd like to see what the possibilities there are for dating, but wanted you to know and also want to see what you think about that?" That way, you're not really asking for permission, but letting her know that you acknowledge her feelings and it gives her a way to have a conversation with you where in the end, she may actually come to terms with it after working it out in a dialogue with you. Either friend will come away feeling grateful that you were honest and open about it. I don't think anyone has a "claim" on anyone. Last I checked, no one owns anyone, and adults are free to date who they want, but along with that, respect for friend's feelings and being honest goes a long way.

    Posted by bklynmom July 14, 09 01:51 PM
  1. This is all about risk vs. reward. Just as Meredith said, weigh whether the reward (catching a great guy) is worth the risk (angering or potentially losing the friend). Remember, often the greater the risk, the greater the reward.

    Meredith, great job on the radio this morning! That guy sure was a rambler, and you handled it really well!

    Posted by sarah July 14, 09 01:51 PM
  1. I'm sorry, but NO woman has a claim of any kind on an "ex".

    "Friends" need to get over themselves, do some intensive therapy regarding their fragile egos, and let their "friends" date whomever they wish.

    Not allowing a friend to date an ex is the equivalent of treating the ex as property. Women, who have moved well beyond being treated as property, would be served well not to treat others as property.

    I'm disappointed in Meredith for being so blind to selfish, insecure women.

    Posted by Sigh July 14, 09 01:52 PM
  1. A friend of mine says that as you get older, your circle of friends gets smaller and smaller. That's just the way it goes, for most people - everyone gets married, has kids, and friendships are the filler between all of that. Doesn't make them unimportant, but it does make them second to family. While there may be 3 billion men out there, the portion of available good ones that exists in any single woman's world is significantly smaller. For all you know, Bill will end up being the love of YOUR life. Do you want to risk THAT for a friendship that will probably fade as the years progress?

    Posted by l'italiana July 14, 09 01:55 PM
  1. My hunch is that people's response to your question is directly related to how they feel about their exes. People who have such strong NO! reactions probably still have a thing for at least one ex... people who admit if you meet and actually have interest in these guys you should go for it are probably happier without their exes.

    What I am trying to say is OTF is probably the only person who can really answer this question for herself. Ask yourseld how you'd react if a friend wanted to date your Ex, and be honest about how you think they'd react. If your friend would selfishly hate you forever (however wrong that might be) its up to you to decide if its worth it or not.

    Posted by Christine July 14, 09 01:55 PM
  1. I'd say both are fair game and you should go for it. And yes, emotions will probably get stirred -- after all, humans always like to wonder, "What if...????" or "If only I had..." But, neither woman has a claim over these guys.

    I guess it depends really on how you think your friends would react. For example, I'm speaking as someone who broke up with a guy (who a week later started dating the girl he'd end up marrying). Then 4 months later, I started dating my ex's good friend... and ended up marrying him. To this day, we all are still good friends, hang out, go to our kids' birthday parties, etc. So, it is possible to be on good terms with your friends even when you date (or marry) their exes.

    Posted by me July 14, 09 01:55 PM
  1. Good luck with all the conflicting opinions! I don't agree with people that say there are 1000's of men out there. Having been in my 30's and single in Boston, I know it is extremely difficult to meet someone. Your friends may not like it, but if it works out they should be happy for you. I say go for it, in both cases.

    Posted by Amy July 14, 09 01:55 PM
  1. Judging from what I'm seeing here with all the attempts to justify risking one or two friendships for a chance to date guys that the LW has never seen or spoken to, I strongly recommend that the LW and her crybaby commentor fans ("There are NO good men out there...AND you're 35 and about to turn into a pumpkin!!! You go girl!!!!") ought to be flooding Meredith with letters for advice on how to get dates.

    If sloppy seconds from current friends is your only available dating pool, then I truly feel sorry for you. All things being equal, it would seem easier (read: less complicated) to ummmm...I don't know....MEET new guys?!?!? It's nothing short of pathetic that these are the only two options presented by the LW and even more pathetic for the commentors to validate this selfishness and laziness.

    Honestly, the pool party girl from yesterday was smarter than this absurdity.

    Posted by Hoss July 14, 09 01:56 PM
  1. Joshua #67 - Are you mentally stable?

    Paul #78, #83, #87 - You ask "what's wrong with her" because she is single at the age of 35? Seriously? You don't know anyones story until they decide to share that with you.
    You both sound extremely bitter, judgemental, and immature. Grow up.

    Posted by Bentley Grad July 14, 09 01:57 PM
  1. Many women are so quick to throw their friends under the bus to get a man. Women know this too. Men wouldn't even think twice about dating an ex without "permission" from his buddy. If I was approached by someone in this situation, it would tell me something about the woman if she hadn't cleared it with her friend. It would tell me that she doesn't respect her friend and would likely not respect me. I'd say NO THANK YOU if I was the guy and learned that the friend wasn't fully supportive.

    Posted by sanity123 July 14, 09 01:59 PM
  1. Hypothetically...
    say the poster met her friend sometime after the friend's breakup with the true love. poster and friend enjoyed a good friendship for a few years but the subject of who the friend's only real love never really came up or was never talked about in depth. Friend married and moved away now it's 16 years later. Poster finds a great man during that 16 year period, dates, and maybe even gets engaged. Poster and friend re-connect and friend finds out that poster's fiance is her long lost true love-even though she is married herself with 2 kids. So is poster just supposed to just dump her fiance to avoid hurting her friend? i think not. date whome ever you want.

    Posted by my own two cents July 14, 09 02:04 PM
  1. Amen Hoss! Seriously! If you are having a hard time meeting guys out there than you have bigger issues. Because there literally are 1000's!!!! The point of this letter was not to debate the "lack of guys" out there but to determine whether dating your friend's ex is a risk worth taking. If it is...good for you! Have fun picking up the pieces of a failed relationship on your own cause you have no friends left. It might not be fair, but it's reality. Get over it.

    Posted by Kathleen July 14, 09 02:08 PM
  1. "Waahhhh! I can't find a guy. Waaaahhh! I can't get a date. How dare you tell me it may not be a good idea to go after one of my friend's ex-boyfriends! He might have a glass slipper that fits me!"

    Posted by Boo-Hoo Brigade July 14, 09 02:13 PM
  1. the only reason I wouldn't want a friend of mine to date one of my exes is because I want my ex to be miserable and my friend, being the great gal she is, would probably make him happy.

    yeah- i'm bitter. b/c the ex is a vain SOB and doesn't deserve happiness.

    Posted by the friend July 14, 09 02:16 PM
  1. Ahh, A bentley grad angry at me...big deal. I must have hit a nerve on that one. Let me guess, you are in your late 20's to early 40's and still can't find the right guy since you've already dated the entire alumni classes from 6 years before and after you. You tell your friends you don't want kids because it sounds better than I am getting too old and can't find a donor good enough to fertilize my eggs. You probably still hang out with only people you went to school with and likely look down on coworkers that went to a state school. Do you drive a Volvo or Lexus? Probably live in a 1 bedroom with a cat and last had a date in 2005.

    I am happily married to a girl not from the area that I met while actually going out and meeting real people from outside my circle of friends. We have a child and a home and jobs and friends from all over. And very happy I spent a lot less on my state education than a piece of paper saying bentley or bc or harvard.

    Tell me? Have you still got your cap and gown in a case hoping someday you can meet the man of your dreams to fertilze you and give you another generation of Bentley grads? I bet you still go on the yearly class trip too? Where are you going this year? Cancun?

    Posted by Joshua July 14, 09 02:18 PM
  1. OTF, I understand your concerns, and I applaud you for your very considerate regard for your friends’ feelings. You are a good friend to be worrying about this. And you’re lucky to have friends who have guys to fix you up with--my (married) friends don’t have any prospects for me (age 38).

    1. Ignore the “chicks before d!cks” posts here. Your happiness matters too. You deserve to find a great guy and love and all that stuff. As women, we’re conditioned to put everyone’s needs first. What would make you happy? Is it keeping your friends happy? (would they do the same?) Or is it settling down with the hubby, house, dog and anklebiters? If it’s the latter, isn’t it worth the temporary discomfort if it results in finding the love of your life with Jason or Bill? Someone once told me “you meet people for a season, a reason, or a lifetime.” Friendship isn’t always forever. Love, hopefully, is.

    2. Don’t listen to the advice-givers here who think you’re a homewrecker or a ho and damaging your reputation. You didn’t steal these guys away from your friends. These guys left of their own volition. Unless they were real jerks to your friends and treated them badly. And if that’s the case, that should answer your “date-or-not-to-date?” question immediately.

    3. There’s enough time elapsed. You’re not scavenging for leftovers here. Your friends have no claim. Jason was ancient history. Yes, he’s the ex of your roommate, who’s probably a BFF. BUT he’s probably not same the person he was back in the old days. Your roomie is either stuck in the past to an unattainable ideal, or she’s really unhappy in her marriage. You can’t fix those things for her, and she’s the only one who can do something about it. Bill was 2 years ago. Again, history. And it doesn’t sound like their relationship was serious, committed or particularly long-lived. Was he your friend’s boyfriend, or a guy she dated? There’s a difference.

    4. If you do hit it off with one of the guys and things look serious, you’ll have to tell the friend eventually. Here’s the thing: tell her as a courtesy, DON’T ASK PERMISSION. Otherwise, you’re putting yourself in a no-win situation. If she says “no,” you’re probably not going to stop dating him. And you’re going to look kind of insincere for asking when you have no intent of complying. Present it as a fact, not a request. Or, alternately, you could ask for her blessing; be prepared not to get it.

    5. You don’t even know if you’ll hit it off with Jason or Bill, so this could totally be a non-issue. Yes, go on those group outings to check them out. It’s less pressure, and it’s less guilt for you. If there’s no chemistry, don’t even mention it to the friend involved.

    Good luck, girlie.

    Posted by Madra July 14, 09 02:22 PM
  1. I absolutely agree with Meredith. These girls are your friends and want to see you happy and so do I :) Go for it!

    Posted by Robin July 14, 09 02:33 PM
  1. How important are these friends to you?

    With Jason, I can't imagine that get-togethers with your girlfriend in Atlanta would be all that fun. Hell, it would be awkward at best--husband and kids or not. With Bill, your friend may be pissed off if you date him, but it doesn't sound like they were together for very long.

    However--I'll reiterate my original question: how important are these friends to you? If you don't care for them or don't really like them, then I guess you have your answer. If you do, if you don't want things to be weird or awkward, I'd go the route of not hurting them and just walking away. There are plenty of men out there, despite what some of the whiners on this site say.

    And you know, to the women here who are whining that there are no good men around when you hit 35--shut it. Seriously. I'm 40, and have no problems meeting men. I'd like to set these women up with the men on this site who whine about how women don't like nice guys and how women are all evil and mental. You trainwrecky losers could at least make yourselves useful by providing entertainment for us well-adjusted folks and removing yourselves from the dating pool.

    Posted by PM July 14, 09 02:39 PM
  1. @ #114 Sanity123: guys ask permission when they’re swooping in quickly or if it’s a girl their buddy was somewhat serious about—men always feel somewhat possessive of a woman they slept with first. There’s a different code between male friends and between female friends.

    Posted by Anonymous July 14, 09 02:41 PM
  1. @ #114 Sanity123: guys ask permission when they’re swooping in quickly or if it’s a girl their buddy was somewhat serious about—men always feel somewhat possessive of a woman they slept with first. There’s a different code between male friends and between female friends.

    Posted by Clue Bus July 14, 09 02:42 PM
  1. OTF, I have never understood the rule of not dating a friend's ex. People are not objects that you can lay claim to. Jason and Bill are both free to date whomever they please. And so are you. If your friends truly want you to be happy - and if they care about their ex-boyfriends and want them to be happy too - they should be okay with you dating either one of them. They might not come to your wedding, but... Good luck!

    Posted by Dee July 14, 09 02:46 PM
  1. Sanity123, women are no less cut throat than men. The "being male is a brotherhood" thing is as big of a myth as the "women are a bunch of cats" myth. In matters of friendships and relationships, nothing is sacred and nothing is predictable. Please, relax with the misogyny.

    Posted by Fievel July 14, 09 02:48 PM
  1. Wow lot's of good posts today.. Rico, you need to change things up because Joshua and Hoss have way better advice than you.

    Hoss- Amen brotha..

    Supposed Bentley Grad #113. aka femi-nazi. Talk about being judgemental. Again, look in the mirror, you are the one being judgemental. Aren't we all judgemental and that is why we write our opinions on this site? Get a clue. Also, look up the stats for single women as they get older!! Their chances of getting married go down every year. As I said before, maybe some of these women should lower their standards down to their level. Women who are single at 35 are always trying to marry up. And yes, it's usually the girl who graduates from the good school but maybe doesn't know how to put her self together and maybe doesn't have the best personality. It's good to have a nice self-image but please be realistic. Just because you graduated from a good school doesn't mean your entitled to Tom Brady..

    Posted by Paul from Wellesley July 14, 09 02:50 PM
  1. Is there a way for you to just meet these guys and see if you are interested or not in a lower stakes environment? It would be hard for me to deal with my friends dating some people I've gone out with because of nostalgic attachments, but I'd be able to get over it (as long as the news was broken to me in a respectful manner). I would NEVER double date with them though.

    It's also interesting that both of these guys seem to be highly recommended by your friends. The only people I'd be REALLY upset about a friend dating would be guys I knew for a fact were bad boyfriends/creeps, etc.

    But you are risking your friendship by doing this, and you'll need to be very sensitive to other people's feelings. TheSee if you can meet them casually, but look outside this small social group as well.

    Posted by Red Sox Rock July 14, 09 02:55 PM
  1. From OTF
    Thanks! Most posts are helpful, those for & against set-ups. A few are just plain mean, but were expected. Also, I’ve tried match, joined sports clubs, taken ski trips, etc. I’m NOT waiting for a guy to show up - also not making finding one a full-time job. If it happens, it happens, if not – my life is pretty great as is. Also, both guys gave the set-ups a thumbs-up before I was even asked. When it came up the first time, I said "NO", but when asked about guy #2 a few weeks later, i thought “should I keep turning down these great guys?” So, I came here for advice. Also, if a friend wanted to date one of my ex’s – I’d probably set it up myself, being single is hard & I’d do what I could for a friend.

    #8 – if you really think there are plenty of men out there 31 – 39, I’d LOVE to know where!

    #15 – “selfish” for considering dating my friend’s bf from 16 years ago?? I also drove 12+ hours for her mother’s funeral, after baking her favorite muffins.

    #64 / #112 – I’ve met both men. I’d say there is potential or I wouldn’t bother.

    #67 – no fancy degree & no cats. I may be alone, but I’ll never be lonely. I’ll take it as a compliment that you think I sound Harvard educated… & Good Will Hunting is one of my favorite movies too.

    #73 –just pointing out that she met him through me. It’s a fact – it doesn’t make me controlling. My friend hosted the party we met at & now wants to set me up w/ him.

    #100. 101, 108 & the many similar posts, thanks –exactly what I was thinking.

    Posted by On-the-Fence, Boston July 14, 09 03:02 PM
  1. You know, I think it would be different if you had kept in touch with a friend's ex or run into him randomly, and romantic feelings developed naturally over time. You can't help who you fall for and sometimes these things do happen. But that's not what's happening here. In this case, you're purposely targeting guys your friends used to date. You haven't kept in touch with them, don't have any particular feelings for either of them. Are you just bored? Desperate? It's creepy enough when young people date every other person in their little incestuous social circle. It's just plain weird when grown adults try to do the same thing.

    Posted by Rae July 14, 09 03:05 PM
  1. My first thought in reading your letter was - no, don't do it, not worth dating a friend's ex ,unless the friend gives the ok right from the get go. But, in thinking about it, I agree with Meridith tread lightly and do the group activity thing, could be that you're not even all that interested in either guy or vice versa and it's a moot point.

    To the people who have said - there's millions of quality people out there, yes in general that's true, but meeting a quaility that person that you actually you click with isn't that easy. So, if you have a chance you should try to take it. That said, you should still consider your friends feelings. If these were recent ex's that your friends were very serious then that would be a different story. However, "Jason" and your friend have been broken up for 16 years and she is married with 2 kids, I would hope that she is over it by now. "Bill" and your other friend only briefly dated and she dumped him so she definitely should get over it especially since he's already said he's not interested. Good luck!

    Posted by cc July 14, 09 03:05 PM
  1. Feivel of post 52 has it precisely right. This issue is not to be over-thought. Give both of these guys a try. If things go well with one of them, everyone SHOULD be happy. Folks who react badly to your possible happy connection with one of these men are immature and selfish.

    It's as simple as what I always tell my 7-year old: everyone has to do what THEY want to do. In this case, date these guys and enjoy yourself, and don't engage in wild speculation about the reactions of others. Things have a way of working themselves out.

    Posted by Jetta July 14, 09 03:10 PM
  1. It's frustrating when the LW writes in to validate what they already know they are going to do. Our advice both for and against was helpful? Yet in your fancy little list you have pulled out all the comments for it, saying it's what you were thinking? Then why the letter?!?!?

    And FYI - Muffins and a road trip do not excuse your poor judgement now. See you on your next letter, "How do I meet new girl friends?"

    Posted by Kathleen is cranky today... July 14, 09 03:22 PM
  1. Not misogyny... Men and women are VERY different in their friendships. That said, my view is that if a man or woman did that without "permission", I feel it is disrespectful to the friendship.

    Posted by Anonymous July 14, 09 03:23 PM
  1. OTF- thanks for calling #67 out on that Plagiarism from Good Will Hunting!!! I was going to myself!

    Posted by love GWH July 14, 09 03:24 PM
  1. I totally disagree - you can never date a friend's ex. Never Ever.

    Posted by Liz July 14, 09 03:24 PM
  1. Post #100 (Catherine) said exactly what I was thinking: "I'm tired of this "it shows what kind of friend you are" stuff. How selfish is it to say, I'd rather have you remain single, while I'm happily married, than have you date someone who didn't like me?"

    Posted by Go Wake! July 14, 09 03:25 PM
  1. Sorry, but I'm just not buying the fact that you keep insisting that your two best prospects right now just happen to be ex-boyfriends of your current friends.

    Also, you wrote in to an online advice column for a reason. You feel uncomfortable about it in some way and are looking for the green light. The only way to resolve it is to ask each of the two friends what they think. Not permission, just feedback. Just as a courtesy and out of respect for them as friends. It's called being an adult. Go ahead. Try it.

    Posted by Hoss July 14, 09 03:30 PM
  1. "Just because you graduated from a good school doesn't mean your entitled to Tom Brady.. "

    And just because you're a Harvard grad and/or aking a lot of money at age 48 doesn't mean you're entitled to a 27-year-old Angelina Jolie. (When I was in my twenties, I wasn't going to go near any 40 or 50 somethings, no matter how much money or success they had.) Just sayin'. Dating laterally goes both ways.

    Posted by goes for you too July 14, 09 03:31 PM
  1. Rico loves the hate and the jealousy and just loved the writers response to the posts...

    Rico still sticks by his opinion of looking beyond the usual places that you currently look/hang out. Rico thinks it is great you joined clubs and tried other methods, he is proud of the fact you took initiative and wishes you the best on that. Rico has a few other places for you to meet men in the age range you desire. Have you tried a singles vacation? Backroads is a great one. How about MFA Friday night's? Plenty of charity functions to go to in Boston as well. Also you could be a volunteer at events or functions or join a charitable cause in other ways. Biking? Running?

    Rico wants everyone to know he is loving the weather and hopes you all are as well...

    Love always,


    Posted by Rico July 14, 09 03:31 PM
  1. It seems that there is much more lurking below the surface here than a question of who to date. What 35 year old still has her college roommate set her up with guys?! Frankly, On-the-Fence, get off the dang fence and find greener pastures. Have you not learned how to cross the street yet? Do you currently live in a nunnery and have no opportunities to meet men? Why are you dating recycled guys? Are you still living in the little po-dunk town that you grew up in? What gives? There are milliosnof men in the world. Dating friends ex's is creepy-no matter how far back they were an item. It's a big world, get out of your box and explore it.

    Posted by City Chick July 14, 09 03:32 PM
  1. OTF in her follow up comment: "if a friend wanted to date one of my ex’s – I’d probably set it up myself, being single is hard & I’d do what I could for a friend"

    Congratulations on the most unintentionally absurd comment ever posted on LW. It narrowly edges out the 7 posts by that reindeergirl person that were previously tied for the top spot.

    Posted by Bob Dwyer July 14, 09 03:43 PM
  1. its mutual friends who are trying to set you up. trust their judgement. do social activities. i dont think its being a bad friend, i just think it needs to be handled carefully, in the sense that first comes group outings, and if something happens than a very open yet not too detailed talk needs to happen between you and the friends- especially bc if you hit it off they will notice, or find out, through your mutual friends.

    Posted by katie July 14, 09 03:48 PM
  1. #139 I agree with you. I'm 35 and married with kids. I will say that some gentlemen that work in my firm are north of 45 and go through a mid-life crisis where they must dump their first wife in order to date women young enough to be their daughter (25-29).. Wether it's right or wrong doesn't lead me to judge. However, they seem to be able to get their fair share of younger women!! Some of these guys are old and look old.

    Posted by Paul from Wellesley July 14, 09 03:52 PM
  1. If you can't find anyone on Match, or POF, or Chemistry, etc., that meets your standards, and are reduced to your friends ex's then as several have already said IT'S YOU! And God help the two you have your eyes on.....

    Posted by Brett July 14, 09 03:53 PM
  1. Look, a woman who is married with two kids got what she wanted - she's married with two kids and shouldn't be pining for an ex-boyfriend from 16 years ago. The other girl made a choice to break it off with the guy so she could date someone else, realized that she was missing out on Mr. Wonderful, and when she came back he said 'Not so fast.' The author of the letter is looking for love and a relationship. Doesn't she deserve some happiness and a chance of being married and having kids too? Perhaps one of these guys or neither of these guys are 'the one', but she should at least go out with them. If it doesn't work out, no harm no foul, but she at least has the guts to try. But I agree, don't mention anything until either of them actually 'go somewhere'.

    As an aside, I just got divorced at 37, almost 38 and I ask myself, where are the 'millions' of men everyone speaks of here? Trust me, before I was married I did blind dates, internet dating, you name it. I found someone who I thought was wonderful, but turned out to be not soo good. Dating now is much harder. Thinking about moving to another state for a fresh start *and* for a new crop of men who I hope are amazing and ready to settle down.

    Posted by Newly Single July 14, 09 03:58 PM
  1. Plagiarism? Yeah, like I was going to actually put footnotes to my post that I got the line from a movie. You are a Jack-A$$. The letter writer picked up on it as it was supposed to be. I bet you are a whole lot of fun at a party? Do you walk behind people putting coaters on the table to avoid drink rings? Goof!

    How do you like them apples?

    I Love Rico, his posts are the best but thank you Welleseley guy for liking mine too.

    Posted by Joshua July 14, 09 04:16 PM
  1. Who started the whole bad habit of encouraging the LW to give us an update? It's gratuitous. I don't need to know how the LW's life has changed since 10:30 this morning. This is not a chat. Chat's tomorrow at 1pm. You want dialogue? Go to a movie.

    Additionally, I'm tired of ampersands. GO AWAY AMPERSAND USERS.

    Posted by Sally July 14, 09 04:18 PM
  1. As for the ladies, OPP means something gifted
    The first two letters are the same but the last is something different
    It's the longest, loveliest, lean-- I call it the leanest
    It's another five letter word rhymin' with cleanest and meanest

    I really like Edith’s way of explaining how to sample the menu without tasting the dish. That sweet wine will give you a headache, but not before it enhances your insight. I vote for Mere to go wine tasting every Monday. OK, let’s get down to it… It’s a MATH problem: If you’re 35 and you have to date and capture one of these fine gentlemen, I would imagine that between the dry heaves of asking or being asked out, the ugly meets and greets, the life stories of past romance and genital comparisons, the awkward intermingling of tongues, the sobering realization that “Jason” is comparing your then 19 year old friend to the now 35 year old you, yadda, yadda, yadda…he’s stepping on a glass at best maybe 2-3 years from now, blah, blah, blah, with the fertility injections and the onslaught of perimenopause your looking at a bun in the oven @ 39 and Little Bill @ 40. I think traditional dating is out of the question at 35.

    Posted by valentino July 14, 09 05:27 PM
  1. #1 (Jason) is definitely off-limits if you value your friendship. My BIL is seriously dating my husbands first serious, long-term GF from about 17 years ago. She dumped him after almost 4 years of dating (she was very young), it took him two years to get over it. Married with kids or not, it kills him to have to see her (and me to have to see him react to her) to a point where we don't go to family functions if they are there.

    #2 is probably doable, but do give your friend a head's up first.

    Posted by Jen July 14, 09 05:37 PM
  1. I think if you are good friend, that shows through no matter whom you date (even exes)

    The dating advice taken should reflect your goals in dating. Do you real want to find that special forever-person (well then the dating advice should be obvious, you should date people who you find interesting until you do)? Or do you want the approval of your friends? I am not saying it is a bad thing to seek approval of your friends, it is just a matter of priorities.

    I w

    Posted by Fred B July 14, 09 06:00 PM
  1. if they're unattached, and your unattached, your all fair game. Go for it !!

    Posted by Pam July 14, 09 06:20 PM
  1. In both cases, if they are genuine friends that want to see you happy, these two women should not care. In case #1, she's married to someone else, has kids, case closed - go for it. I'd also chat with her about it at some point, I bet she'll get a kick out of vicariously living through you as you date him. Case #2 seems a little stickier, she might still harbor some feelings for the guy since it was just a couple of years ago and she felt she made a mistake dumping him. I'd talk to her first if you want to hold onto her as a friend. If she's still single, then I would do that for sure, she might take that news a lot harder than case #1 will. At 35, your dating options dwindle a lot. If these are 2 good guys with potential, and these women are real friends, it shouldnt matter.

    Posted by Whatever July 14, 09 06:33 PM
  1. I say #1 is fine. With guy #2, maybe wait a while longer.
    I'm 35 and single too. It sucks being single at this age and it just gets harder and harder every year that goes by. I hope one of these guys works out for you.

    Posted by lisa July 14, 09 06:55 PM
  1. I haven't read too many of the other responses so i hope i'm not being repetative but...since you have not met either guy I would avoid the situtation all together. No point in getting into this potential conflict with your friends. Again I say this because you have not met the guys. Emotional involvement is minmal at this point. I liked what Rico had to say so I would read his posts if you haven't yet. In reference to his post, I will say that it may be easier said than done, but definately worth thinking about. There are other options-Good luck!

    Posted by JP July 14, 09 06:59 PM
  1. poster #36, I am so totally agree with you. You don't date your friends'ex at all.
    You will hurt her feeling. I hate hurt others feelings. especially someone you know
    and care about.

    Posted by stephanie July 14, 09 07:32 PM
  1. Kathleen does seem a little grouchy today. I always enjoy her input.

    Friends wont tell you they dont want you to date their ex. My brothers (4) and I always had an understanding, "no dating the ex of one of the other brothers". If theres hurt there, from the breakup, it could be ugly. Its just a bad idea. Of course, they will tell you its ok, but its really not. Sometimes it works out, but for the most part, dont do it. Its not worth it.

    Posted by billy13 July 14, 09 08:04 PM
  1. Everyone has regrets in life, and the ones of the most consequence tend to be from love. The girlfriend to be most injured will be the married one. Of course.

    Should you? No advice on this. You have no attachments to either men that you express. Unless you left something out. Any old attractions you felt back then? Or merely a dry spell and some anxiety on getting older makes you consider them? Reasonable feelings none the less.

    As we age, those we knew in our youth hold such significance in our hearts. And this is not just my opinion on the matter. From Howard Hues to George Washington and FDR, those we knew when we were young have a special intimacy, a special place superior to those you meet later in life. It's lovely, really.

    The man from two years ago is of no consequence, or should not be to someone reasonable. The love of her life. Well, now, does that knowledge of something so passionate tempt you? A naughty delicious attraction?

    Well, do make note, he may feel some special spot for her as well. If you get your ideal, you have him, how comfortable are you with her being someone he will always love? If I may be so ridiculous as to say imagine you marry, do realize that you, as the wife, will eventually turn into the routine and she will be the long lost love who is occassionally on the phone or coming over - whom he remembers making love to while he politely grills hotdogs for her kids. Does that sit well with you?

    If you pursue these men, or even ask to, your friendships will change with these women regardless of whether these relationships pan out into anything meaningful.

    You cannot have your cake and eat it. So who do you walk away from? That's up to you. Only you know the value of these relationships and the burden of falling in love with a man who has made love to your friend.

    But you will walk away from someone, the men, or a friend. Such is life.

    Choose wisely.

    Posted by a few grey hairs and whole lot of life behind July 14, 09 09:58 PM
  1. Sixteen years ago is ancient history--if your old roommate has a problem with you dating this guy, it is her problem and not yours. Maybe run it by her just to humor her, but really she has no say. Two years is a little more recent, but only because she more recently tried to get him back. And got rejected. But again, she will need to go cry on another girlfriend's shoulder. I'm thirty and was in love a few times before my current relationship, it doesn't give me rights over those guys. Might be a little awkward at first if one of my girlfriends starting dating my ex, but within a circle of friends, it's bound to happen. Now that I think about it, half of the couples I know wouldn't be together if friends' exes were off-limits. We're not in high school--date who you like! Anyone who is your friend should be happy for you, period.

    Posted by formerbostongirl July 15, 09 12:19 AM
  1. Get thee to a nunnery. Or at least graduate from high school. You're 35 for God's sake. Time for you and your girlfriends to grow up.

    Posted by Youbrokemymoodring July 15, 09 06:05 AM
  1. It doesn't matter if the boston.com world says it's ok or not ok. Regardless of what we say you are gambling with your friendship.

    If the risk is worth the possible rewards than you do it. Otherwise, give online dating a try :)

    Posted by Gamble July 15, 09 07:43 AM
  1. OMG! The person who said that this is a chat rather than an advice column is so right. First of all I agree with the person that said the LW has probably made her decision and is just looking for confirmation. My feelings on this are very simple. What would the girlfriends do in this situation? One lives in another state and is married with children....while she's living her life in the coupled world, the LW is looking for a relationship. The other friend moved on, so what is the question here? If these 2 guys are willing to be set up, then LW should go for it. I believe that friendship between women is sacred, however, when you are 35, the available men are scarce. Most of the men that want 35 year olds are in their late 40s, some have already been married and divorced. My advice - go out with them, test the waters, you may not even like them. It would be a totally different story if you snatched them away while your friends were actually dating them. Try on the shoes before you walk out of the storeEnjoy.

    Posted by beenthere July 15, 09 08:12 AM
  1. I am in the situation of being like Jason's ex. He broke my heart. It's been a while, but if one of my friends wanted to be with him.... well, I just don't think I could handle seeing HIM happy. But talk to your friend, listen to her and see if you two can figure it out. As to Bill - tough luck to your friend - the grass is not always greener on the other side.

    Posted by single and finally happy July 15, 09 08:18 AM
  1. Paul, these guys will soon be divorced and whining about their gold-digging trophy wives who are taking them to the cleaners. Sure, they can find someone (in rare cases) but most twenty-something women can't be bothered with aging men who feel entitled to arm candy. They'd rather be with guys their own age--way hotter, and they have more in common.

    I just think it's a bit hypocritical to lecture women to start opening their minds and their horizons when many men refuse to do the same. I can't tell you how many men I know whine about how they can't find anyone, and then dismiss viable women as too old or not pretty enough--even though they're a couple of years younger than these men, and these guys are balding with a paunch--not exactly hotties themselves. And last time I checked, your average male Harvard grad wasn't giving the cleaning lady or the cashier at Target the time of day, or considering her for marriage. Again, just sayin'.

    Posted by goes for you too July 15, 09 09:18 AM
  1. At 35 most single people have a few (or more exes). If in a small town like Boston you restricted your dating to "fresh meat" it could be a long time before you date again. If your girlfriends (hate that word for women -- we're not 14) think this guy is absolutely someone you MUST meet and date, that's another story. As long as they're not sending someone your way just to do so, or to avoid hearing you whine you aren't meeting men, then fine. BTW, Boston might be THE worst city for meeting men. My experience is men think they're too good for the women in Boston.and are very judgmental and unfriendly (unless they're drunk).

    Posted by Lauren July 15, 09 09:47 AM
  1. The whole "if they were real friends, they would be happy for me" goes both ways. They can also say, if you were a real friend, you wouldn't date my ex. Bottom line is, you really have to consider how important these friendships are to you - because logic and fairness often have nothing to do with how a person feels. Odds are good that, permission or not, dating either one of them will be seen as a betrayal of sorts. In their eyes, it's about loyalty, not staking their claim on someone. Which is not to say that you don't have a "right" to move forward and date these guys if you really want to - but having a right to do something does not necessarily make it the best course of action. Personally, I would walk away from this situation, unless you're really prepared to face the drama and hurt feelings this could potentially cause.

    Posted by Sluggo July 15, 09 09:50 AM
  1. its absolutely ridiculous. there are so many petty jealouse people out there, If they were walking in your shoes I'll bet the sage advise would change.

    In both of these situations it seems that you should see if your interested, the case that happened 16 years ago, It may as well not even be the same man, people change so much in 16 years, and your other freind dropped the guy, Hello!

    She has no-one to be upset with but herself, Its very big of you to even pose the question, and then have to read all this advise.

    and who knows? maybe you won't even be interested in them, and if you do feel the slightest bit Guilty, I'd say go look for other men, because guilt is not a good foundation to start a relationship on.

    Posted by WLM July 15, 09 10:04 AM
  1. I was in a relationship for a year with my boyfriend (now ex) and when I was with him I had this funny feeling that my friend liked him. Now this friend wasn't just an aquaintance, she was a friend...someone I discussed my relationship with. She was also a big help to him and his family (as a favor to me) when we were together because of what she did for a living and where she worked. That is all I can say about that.

    Well we broke up (his decision) and my friend started acting strange...she started hanging out with his friends more, joined the gym he belonged to...always talked about him and to me, etc. Truthfully, I was just waiting to find out that they were together. Well, about three months after we broke up, I know longer had to wait. They were dating. She actually called me and said we never meant for it to happen..it just did. OH right, sure it just happened.

    I am no longer friends with her or with him...and never will be. They have made some wild accusations about things they think I have done...and that is just unforgiveable.

    So for me, reading this made me think about what happened. All I can say to OTF, is think about both of these friends and how you would think they would react. I don't think anyone can tell you what to do...you need to make that decision. Good luck!

    Posted by littletap July 15, 09 10:39 AM
  1. First, anyone who calls women older than 25 "girls" is annoying.

    It sounds like the chance of meeting a guy who may or may not be a good fit is more important than your friendships. If it is, then so be it, though it seems pretty sad and desperate and makes me think these friendships are more superficial than substantive.

    By the way, you are seeking them out now, so that "logic" holds no water. You have choice, exercise it, cause with either guy it will change the dynamic of your friendships. It's different if you met the guy, didn't know, formed a bond, then found out later. But that's not the case. You know now, so the choice is conscious which means you need to take personal responsibility for it.

    Posted by yupokay July 15, 09 10:57 AM
  1. I have to agree with Meredith on this, take it easy, go out with both guys in a non-date setting to see if you have any interest, or see any potential, then go from there.

    Guys aren't much different, we expect our friends to not date our ex's either. What sucks is that there were a couple ex's of friends who I liked and were friends with (in some cases, I was friends first before my friend dated them), but didn't ask out, and I regret it, esp. now, looking back and not being friends with those guys anymore. One of them, we stopped being friends when he left for basic training. If I knew then that we wouldn't be friends, I think I wouldn't have cared as much and asked them out.

    As for #158 (a few grey hairs and whole lot of life behind), I have to disagree with part of what you say. You said that "those we knew when we were young have a special intimacy, a special place superior to those you meet later in life."

    I think it depends on your life and what happens to you as you get older and develop friendships. I have friends now with whom I have that same "special intimacy" or more then my friends from when I was younger. Some of them are superior to those I knew when I was younger. In fact, I wish I had them back when I was young.

    Posted by C.J. July 15, 09 11:00 AM
  1. Whoa, I'm married with 2 kids living in Atlanta and was in college in Boston 16 years ago. If you're one of my good friends, and you want to date the one that broke my heart go right ahead. He was a great guy, and a lot of fun. I have a wonderful life now that I LOVE and a family I wouldn't trade for the world. I want you and him to be just as happy!!

    Posted by Lynne Cole July 15, 09 11:08 AM
  1. OTF,

    The situations with both guys is completely hypothetical at this point. I'd try the whole group meet situation Meredith mentioned with each of them. After all, this may or may not lead to you dating either of the guys anyway. As someone pointed out earlier these guys have their own thoughts/feelings/desires and may/may not be interested in dating you.

    If the group meet does lead you to dating either of these guys, then I'd say you need give the friend who dated them a heads up. Depending on the friends involved this may lead to you losing a friend, only you can decide if the possible relationship is worth it to you. As several other posters have written, no one owns the people that they dated previously, but some people do have attachment issue with prior loves. So if you know your friends are like this be prepared for issues if you go forward with dating either of these guys. Good luck with whatever you decide.

    Posted by sundiego July 15, 09 11:16 AM
  1. Ban Rico!!!

    Posted by byubba July 15, 09 11:53 AM
  1. better grab one quick before you officially become an old maid.

    Posted by lifesucks July 15, 09 01:59 PM
  1. dating your friend's ex is a no-no in my book. It becomes awkward and could potentially ruin your friendship with your girlfriend.

    Posted by joycejohnson July 15, 09 02:37 PM
  1. that so despreate to me poster#174. some people like to put their career first.
    and some like to put their man first. In this 21st century, you don't call single an
    old maid or whatever.

    Posted by stephanie July 15, 09 03:31 PM
  1. “What’s a Friend to Do” Haiku

    Girlfriend’s boy-toy leftovers
    Doggie bag to go

    Posted by val July 15, 09 04:18 PM
  1. Jason may have dumped Friend #1, but that was 16 years ago. She should be over it by now. Bill, while involved more recently with Friend #2, was Friend #2's dumpee, not the dumper, so that's her tough luck. Be gentle about it, but don't feel reluctant to see if either of them floats your boat.

    Posted by david in ohio July 15, 09 04:45 PM
  1. #164- I agree these older me are grotesque but some women can overlook that when they summer beachside on Nantucket. I’m not saying what they are doing is right or wrong but it’s just a fact of life. It’s not the life I would sign up for… I’ll say, you should never date one of your friends ex’s even if they say it’s ok unless you don’t value your friendship. There are plenty of opportunities for women in there mid to late 30’s to day. Stop whining and get out there. Again, these girls need to date men at their level.. So they have a blue-collar job or a few pock marks… So what! Maybe you’ll find your soul mate.. All I know is that my wife thanks her lucky stars everyday as I have given her a good life and beautiful children…….. Just kidding..

    Posted by Paul from Wellesley July 15, 09 04:49 PM
  1. People are living complex beings, not property. Date whoever wants to date you. Life is short. No one is off limits. People need to be mature. If it didn't work out for you... too bad... bad timing.... it takes 2 to tango. Dating is like the train. There's always another one on its way.

    There are 5 billion people out there... are people going to have emotional issues over 1 person? Free advice.. be the best person you can be (honest, friendly, hardworking unselfish) and if someone wants to be with you... then they will be.

    Posted by unselfish July 15, 09 04:57 PM
  1. Glad I got in on the tail end of this one, I've got a lot to say on it.

    First - Please stop calling grown thirtysomething women "girlfriends". We all left the schoolyard a long time ago.

    Essentially all these posts are coming down to who or what is more important. Your friendship with your friends, or your potential serious relationships. (I assume there is an element of seriousness to OTF's intent).

    Caveat: I'm not getting down on friendships, I'm really not. True friendships are one of the great gifts in life, and I'd never walk away from one if I could help it.

    That being said, let me say something. In my opinion in a permanent, loving, committed relationship, the person I'm with is at the top of my list of priorities on the day-to-day. She is the first person in line who deserves my time and attention. That just makes sense. She is the one I go to with talk of life-changing issues and serious topics. We pay the bills together, clean the house together, go to weddings and funerals together. We argue, we fight. We make up. But we're there for each other in very basic, and very real ways my friends simply aren't and never will be.

    She has earned that place at the front of the line. And I've earned that same place from her.

    If there was a woman I was seriously interested in, and I had a friend who dated her a few years back and took issue with it - I'd tell them to go to hell. Things would be rocky with him for a while. He'd call me 'whipped'. Or a crappy friend, or claim my 'man-card' is revoked or some other juvenile garbage. Whatever.

    As time goes by he'd either come around or he wouldn't. But I'll be damned if I let anyone else tell me who I try and build a life with, take a shot at happiness with. A real man takes care of his lady first, that's just the way it is. If he can't, he doesn't deserve one.

    That might make me a less-than-great friend. But it makes me a damn fine boyfriend/husband.

    I've got friends - guys mostly - who live and die by their friendships, that "no woman will ever come between us." And every last one of them, well into their 30's, is a career bachelor. Because no woman wants to think they're second fiddle to your friend. And let me tell you all a secret - no man wants to either, even if they don't admit it.

    Perhaps... just perhaps... this whole friend-before-anybody mentality.. is contributing to the demise of relationships everywhere. It's a self fulfilling, self perpetuating system where, if your friends are so important to you that they can literally tell you whom to date, and no man will EVER be as important to you as your friends? Well then no relationship will ever work for you. And if it does, if you find a man who deserves to be at the front of that line and you put him there? You get the "bad friend" label. It's a trap.

    Since when did "friendship is forever" replace the committed nature of an actual marriage? What, friends are forever, but spouses come and go? That's kind of backwards thinking, don't you think?

    Maybe we all ought to loosen the reins on our "ya-ya sisterhood", "man-card-having brotherhood" mentalities a little and re-prioritize. A friend, a TRUE friend, will look out for your happiness, especially if it's something as inconsequential as an ex boyfriend from 16 years ago, no matter what they meant to them. If you're still pining after 16 years to the point where you just coulden't BEAR to see a good your friend happy with them? Seek some therapy.

    Sorry, I went a little off-track there. But I think I've made my point.

    So really OTF - if it's that important to you, sit down with your friends and lay it out. You're going to ask this guy out, just wanted to let them know. And whatever they choose to do, they do. Just make sure you can live with the consequences.


    Posted by Ceej July 15, 09 06:08 PM
  1. Ceej,

    This is the most intelligent, non-gender-biased post ever on this blog.

    You didn't win on numbers. But IMHO you win huge on quality.

    DAMN well done.

    Posted by SettleDown July 15, 09 11:48 PM
  1. "Again, these girls need to date men at their level.. So they have a blue-collar job or a few pock marks… So what!"

    Again, men should ALSO really take this advice (BTW, at 35, she's not a girl, she's a woman. I'm not calling you a boy, so can you kindly drop the girl thing? Coupled with "men" it sounds gross). I'm not seeing a rush of men to marry the cleaning women at their offices or the cashiers at Dunkin' Donuts. So they've got a few extra pounds and have menial jobs. So they don't have perfect dewy skin and are maybe closer to your age. So what!

    I don't want to hear any complaints from MEN about how hard it is to find women when THEY won't expand their search either.

    Posted by goes for you too July 16, 09 09:05 AM
  1. Mere is so on point here. I was thinking the same thing about Jason`s Ex. She might not react well to you dating him. However she is married and lives in ATL. Therefore, I say follow Meres advise and feel it out. You never know Bill or Jason could very well just be "The One"!
    Good Luck!

    Posted by Lilshorty98 July 17, 09 09:02 AM
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Meredith Goldstein is a Boston Globe columnist who follows relationship trends and entertainment. She offers daily advice on Love Letters — and welcomes your comments. Meredith is also the author of "The Singles," a novel about complicated relationships. Follow Meredith at www.meredithgoldstein.netand on Twitter. Love Letters can be found in the print edition of The Boston Globe every Saturday in the G section.

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