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Almost 40. Never dated.

Posted by Meredith Goldstein  February 4, 2009 10:58 AM

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Almost 40. Never dated. Let's help.

Q: How do I get into the dating world? I'm pushing 40 and never really dated. I'm probably too scared to date at this point in my life and too embarrassed to tell anyone that I"ve never really dated anyone or had any kind of relationship.

The last time I actually dated a guy, I was in college - a summer fling, really. There have been guys I've been interested in but they have never been interested in me. And guys just don't seem interested in me. A bit on the overweight side, but I am active in many activities And I have many friends. I tried online dating once but never got any interest and got frustrated and gave up and don't see much sense in going back.

Over the years, I've had different priorities (making friends since I'm not originally from here, job, etc). Now I'd like to see what this dating world is like and maybe find that someone special. But I get tired of people (usually married) saying oh .. you'll find someone . There's someone for everyone. Well, I haven't found anyone - just to date.

Is there any hope for someone like me? To find someone .. anyone at this point.
hopeless_in_dating, Waltham

A: Oh, Hopeless. It's never too late. And I'm sure many readers would agree that it's not easy to meet people.

That said, I do find it odd that you haven't met anyone online or in real life since college.

My advice? Stop being embarrassed about your drought and start soliciting help. Tell your friends you want romance and ask them for guidance. Tell them to be honest with you -- even if it means hearing real criticisms. Your friends are the best way to find out whether you're giving off the wrong vibes, whether you always smell of lunch meat, or whether there's something you do that makes people think you don't want to date. These friends can also look over your online dating profile and tell you how you're marketing yourself. You need lots of dates. Online sites are the easiest way to find them.

They made a whole movie about this starring Steve Carell. In the end, he gets sex. And love. And great friends. Just because he's finally honest about his needs. That could be you.

Readers? Can you give Hopeless some help? Share your thoughts here.

Also, get ready to chat at 1.

-- Meredith

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68 comments so far...
  1. Get your friends to set you up.
    Also, go to "pick up" bars. Try Lucky's in South Boston. All of my exes have found signifigant others there.

    Posted by Situation February 4, 09 12:10 PM
  1. There's more here than meets the eye, and I agree with Meredith that you need to get honest feedback from someone. It sounds mean, but you are doing something wrong -- looks, personality, vibes, something. Find out what it is and correct it.

    Posted by Raffi February 4, 09 12:15 PM
  1. I recommend counseling, don't be afraid to LET yourself.

    You have to be happy with yourself for who you are, and it's AWESOME that you wrote into the paper with this question.

    My sister is in the same social situation, what do you advise I tell her?

    I've signed her up for online dating, I've set her up with guys, but nothing has clicked.

    Posted by FrankD! February 4, 09 12:55 PM
  1. I don't mean to be hurtful...but do you have a weight problem? Or do you expect men to do all the work? If either of that is the case, you may need to be more proactive, but first check with your friends and do ask for their honest opinion of you.

    Posted by Jack February 4, 09 01:01 PM
  1. What about speed dating? You might not find the love of your life, but at least you're putting yourself out there and meeting people. Practice!!

    Posted by hohum February 4, 09 01:03 PM
  1. I am in the same situation. I am 41 and never dated and hitting 42, but I have started to open up my eyes, talk to guys more often, and I should admit that many of them when they hear that I have not dated, they get really scared or wonder why. Some think that they should start teaching me things, and feel like they do not want to have a kid around. Others are very appreciative and are very very happy to hear that I will be excited for any thing that goes on. Do not worry about it, just go for it.

    Posted by Newengland123 February 4, 09 01:03 PM
  1. Try to open your social network to different people, you never know who will be a good match for you. They say opposites attract, but that is not always true, so don't rule anyone out. You seem like a real down to earth person who has a lot going for you, so don't get too discouraged and keep an open mind.

    Posted by MF February 4, 09 01:04 PM
  1. I'm convinced that some people really are not cut out to be in a relationship (dating, boyfriend/girlfriend,married, or otherwise). I had two former friends (both female - both around 40). They "talked the talk" and always professed that they wanted to date and find someone, but when it came right down to it - they could not (or would not) "walk the walk." They would choose the wrong person - on purpose (unavailable married men), make bad dating choices for drama's sake, sabotage their relationships over trivial matters. They will never have a serious relationship, let alone a marriage. So, I would ask yourself this question: do you REALLY want to date, and put in the time and the effort that is required? If so, go for it. But by 40, we're all pretty set in our ways. Be prepared for lots of compromise and flexibility. I have to be honest - I find it very odd that you have not been involved with anyone else - at any level - by forty. That would be a red flag for me.

    Posted by Scotty Boston February 4, 09 01:14 PM
  1. My advice would be 'relax.' While Raffi is right that you may be doing something wrong and that it should be corrected, the far more likely culprit is that you stop being you and that it drives the quarry away. I've seen too many people tense up, act or speak strangely, be ungainly, be embarrassing to be around and it's all some deep-seated fear that being themselves is somehow a bad thing. If any of this sounds like it applies to you, then you only need to decide to let the chips fall where they may. Relax, be yourself, and the quarry will come to you!

    Posted by Roland February 4, 09 01:17 PM
  1. I think you shouldn’t hold back the side of you that you’re probably afraid to show. Become the go getter. Want what you deserve and you can’t go wrong. You should take your strongest asset weather it be your smile, back end lol, etc and let it show. Being big can also be beautiful. That’s something you truly need to believe.

    Posted by Woodline February 4, 09 01:27 PM
  1. Try eharmony.com. One of my college roommates was in the same exact situation and she found her husband there! It's not like match.com or the others where you're matched by the computer. eharmony.com has real people in the background matching you and when you sign up they have you complete a lengthy profile with which they use to match you.

    Posted by nz February 4, 09 01:28 PM
  1. Online dating is the easiest way. But don't limit yourself to one site, sign up on many different sites (Match, Eharmony, Chemistry.com, OKCupid, PlentyOfFish, etc). There are also sites that are more designed for flings or one night stands which could be what you want to get comfortable with intimacy again. Definitely concentrate on making yourself stand out in your profile, get active in conversations, and don't hide from who you are. Also, you could try speed dating where you meet several people for 10 minutes each at a bar for example.

    Posted by Josh February 4, 09 01:33 PM
  1. Also look at your expectations for your 'dates'. Sometimes the standards that you set for others may be unrealistic. So in addition to the other advice, take a look at what it is that you are looking for, not finding, and whether it matters.

    Posted by Powerbar February 4, 09 01:51 PM
  1. For men and women, it's the same: You have to develop an interest in people. Before dating people, you have to practice some basic social skills such as, participating in a group conversation, paying someone a compliment, following up with someone who's recently shared something personal with you. Sharing something personal about yourself, when the situation allows.
    The second thing is to develop an external view of yourself, or a "noticer". How would this noticer view you, day-to-day? If that information suggests changes to you, then make the changes. None of this involves being fake, but rather what we all do in polite society. Then one can register in all those fun dating pages.

    Posted by The Coach February 4, 09 01:53 PM
  1. Just stay positive and stop being a "Debbie Downer"...

    go to the gym...you'l help yourself feel better and lose some weight too...

    Posted by Me February 4, 09 01:54 PM
  1. "Activities" are good, but they are most effective if they are teamwork. When you and a bunch of people are working together - putting up a show, serving at a shelter, discussing church policy - it gives you a good start on a relationship without the pressure of "dating". From my experience, I would suggest sailing (Community Boating, Boston Sailing Center) as team activity where there are more men than women.
    If you FEEL overweight, it may hold you back. You can either lose weight and worry, or learn to move and enjoy it . I suggest ulimate frisbee, martial arts or contradancing. Once you can move with grace & power, you will not feel overweight.

    Posted by Dotreader February 4, 09 02:06 PM
  1. It's hard to let down your guard especially if you have been hurt or put down or ignored before and then to pick yourself up and go out there and date again. You definitely need a "wing woman" who could tell you what you're doing wrong or maybe the type of person you're talking to. Most men are attracted to three things - a woman with a beautiful smile, a woman who listens, and a woman who is feminine. Just because you're overweight that shouldn't get in your way to work on those things. Go where the men are - join a group where women and men work together on constructive projects like Habitat for Humanity, a hiking club, a church group. You're showing off the best of yourself and you're being part of team.

    Bars don't necessarily work all of the time.

    Posted by lolipopp February 4, 09 02:08 PM
  1. Your biggest problem: your letter reeks of low self-esteem and uncertainty. This is the #1 turn-off to most guys, at least the decent ones that aren't looking for easy prey. Work very hard on this, and consider counseling as Frank suggests. There is no point in being embarrassed over something you can not change. Until you become more confident, nothing will change with your situation.

    Online dating can be as shallow as any other medium. Make sure you use good (but honest) pictures, even if you need to see a photographer. Share your real self in your profile, not just what you think people want hear. Show confidence. If it turns out that your best qualities are internal, consider speed-dating or other singles events where your personality will come across clearer than online.

    I wish you luck!

    Posted by Tibbs February 4, 09 02:14 PM
  1. I wouldn't say you're doing something WRONG, but you may not be giving off the "dating vibe." There are more people in this position than anyone realizes. Remember the dating world with people who WANT to date can be just as difficult and drought-like with the only difference being that there are too many dates that don't lead to anything. And don't be embarrassed! Just be thankful you don't have a checkered past that a date can dig up. Men in their late 30s and early 40s are a prime age group, more mature and stable. There are plenty of them dating the wrong people, or having been married to the wrong people and now divorced, who would be thrilled to be in a serious relationship with a woman who's settled into her life and learned how to take care of herself before searching for "the one." (In fact, by this point, you may be too good for a significant chunk of them, so don't get discouraged if you have any unhappy endings.) YOU'RE NOT HOPELESS.

    Posted by Cool Beans February 4, 09 02:16 PM
  1. Make sure you are "open" to situations. Relationships don't come in cookie cutter format. My current boyfriend had never had a relationship. He was 28 when we meet and I was 40! He said if someone had told him they would set him up with a 40 year old, he'd never have gone on the date. I would have said the same about a 28 year old that had never had a relationship. But, it's been almost 2 years and we are very much in love and get along fantastic. Good luck and God Bless!

    Posted by DieselG February 4, 09 02:18 PM
  1. I mean this in all seriousness, and to be helpful: have you considered trying to date women? Perhaps men aren't sensing any interest coming from you, for which there could be a good reason. I've known a couple of women in similar situations; they slowly realized that their lack of "success" with men was actually due to a lack of interest in them, but they hadn't been exposed to the possibilities of relationships with women (didn't have any gay friends, so focused on meeting men they hadn't considered anything unconventional, etc.). If you think you might be at all inclined that way, give it a try; it might strike a chord. If it's not for you, you'll know (or maybe you already do).

    Posted by Observer February 4, 09 02:20 PM
  1. Don't date.....your not missing anything.
    Anyone you meet will be an expert in deceit and will rob you blind.
    If you dated like everyone else did (by starting young); then by 40 you wouldn't even want to date period! It's a horror show out there....you are not missing anything except heartache and deception. Keep your peace of mind and get a "hobby" that you like....

    Posted by Anonymous February 4, 09 02:25 PM
  1. It may be something as simple as your breath. I once dated a girl who had the worst bad breath. It was medically bad. I used to keep a bottle of Listerine in my car so I could sanitize my mouth after kissing her. I couldn’t bring myself to discuss it and I broke it off. She was a wonderful person but I couldn’t get by it.

    Ask you friends to be brutally honest. It may be hard to hear, but it’s a kindness. If there is something, then address it or go to a doctor if its something you cant change on your own.

    Posted by Anonymous February 4, 09 02:28 PM
  1. You are not hopeless by any means. At 39 I found the love of my life online, after years and years of 'voluntary' singlehood. I am not a size 4 (Lol......who is!) and trust me, there are online sites for all shapes and sizes. Many men perfer a woman with meat on her bones! Start out slow, having your friends help you with a profile. Many sites are free, don't be lured into the expensive ones. Post a photo, and be smart about who you respond to and meet. Also, online is not for everyone. You may meet the love of your life in church, at the library., buying groceries, or walking your dog. Keep up the social activities, and don't be afraid to meet new people. Most importantly have fun and be yourself. There is no schedule or timeline you have to keep.for anyone but yourself......you will find love at your own pace. Good Luck!!

    Posted by Lucky in Love at last..... February 4, 09 02:34 PM
  1. Try meetup.com. They have tons of activities for all different interests--sports, hobbies, travel, movies, etc. You'll be out having fun and meeting people while doing things you enjoy. Not all events are designed specifically for singles, but you'll have a good time anyway. I've met both platonic friends and dates that way. Good luck!

    Posted by runrun61 February 4, 09 02:51 PM
  1. Aside from some of the other comments, what are you expectations? I've heard the riff a lot from female friends of "The guys I want aren't interested in me, and the guys interested in me I don't want." Well, yeah, most people fantasize about waking up to the prom king or queen, a movie star, or that terrific, successful coworker, and most people DON'T fantasize about the "losers" they know. This may sound harsh, but I'm going to say it anyway: 40, overweight and never dated isn't in a position to be choosy. The guys available for you to get are going to be likewise 40, tubby, receding hairline and not successful in business. Wrap your head around that.

    Posted by Kittencat February 4, 09 02:52 PM
  1. After my divorce, I vowed to myself that I would be more open to ALL people. I pressed myself to engage others - men and women, young and old - in friendly conversation whenever the opportunity presented itself: waiting in line somewhere, getting a coffee, out with my friends, on the train - anywhere where small talk with another person was safe and appropriate. I can't tell you how liberating an exercise this can be, and how many nice interactions I continue to have with others on a daily basis. I now know that my previous vibe, whether I realized it or not, was one of unapproachability, and that I had been missing out on the great pleasure of simple connections with others. When the time came for thinking about dating, I was already comfortable with pleasant, casual interactions, and meeting men came easily because of that. Thank heaven I grew in this way - I never, ever would have been in the wonderful relationship that I am today if I hadn't been brave and open enough to engage in the casual chatter with a fantastic man who ultimately became my beloved boyfriend!

    Posted by Jetta February 4, 09 02:53 PM
  1. What do you look like? are you sure maybe you are not into woman?

    Posted by Josh 26th February 4, 09 02:59 PM
  1. Oy! Are you nervous around men? Do you have male friends? I would suggest practicing conversation with your male friends and co-workers...No need to send out a lefty to face a lefty. Then, concentrate on making friends...not dating, per se. Allow the guy the opportunity to see you as a great person first. I agree that online dating is a good idea. These guys are there to meet people. There's no mistaking their intentions. However, in your situation, I worry that you won't be able to be decerning as to the quality/truthfulness of the guy. Be prepared that some may be there for sex, some are married and others are also afraid. All of that is OK. It's the experience you're looking for. Don't be surprised if things don't go like a storybook. But use it all to get to the next level. Remember, there are awkward and inexperienced guys who are having a tough time meeting women out there. Don't be shy and beef up that self -esteem. Romance or not...Be someone that someone wants to spend time with. You'll find someone . There's someone for everyone.

    Posted by Dr.(boy named)Sue February 4, 09 03:07 PM
  1. I'm just like you, but in my late 40's and I really don't know what to do. I'm not a guy who drinks, so the "bar scene" wouldn't work for me. I worked for a law firm for 9 years and was attracted to a couple of the women but, being only a legal assistant, I was too embarrassed by my low position to even ask one out. I am only a little overweight myself and am losing the hair, but I'm average looking, not ugly. I even had a couple of married women come on to me, which was really embarrassing and not that easy to turn down because one of them was really hot. But I guess the truth is I'm too shy and don't like to be rejected. I'll be anxiously watching the advice here, because I need to "get a life" myself.

    Posted by Alone February 4, 09 03:11 PM
  1. Get involved in activities that (a) you enjoy and (b) have a social element that includes singles. It's a great way for men to get to know you, and you to know them, without the pressure of a 'date'. Once men have the opportunity to get to know you beyond an initial impression and see you in action, you might find that some of them are interested in learning more.

    Posted by GregP February 4, 09 03:18 PM
  1. Being from Waltham myself, I can give you some specific places that nice people of your age group hang out. And if you are in places with lots of socially mingling people, it's more likely you'll bring up your social skills and work toward your dating goal. Okay, in the summer, the Farmers' Market is the heart of the town. Volunteer or just go every Saturday. There's music sometimes. Back Pages Books has tons of readings and lectures and you can strike up a conversation with the person next to you. The Jazz Cafe: go there with a friend and talk to someone at the next table. Half the people there look as if they're looking for some human interaction as they're hunched over their laptops. I could go on, but you get the picture. Staying local means you run into the same people over and over and can build up your acquaintanceships into friendships and into more, perhaps.

    Posted by Sasha February 4, 09 03:22 PM
  1. Being single for 4 yrs so I tried with eHarmony.com which I got success with meeting single Mom with kids. After several dates with women and chosen the person I feel comfortable with. The dating with her still going strong after I met her in person since last Sept. The site are much better than any date sites that I've been used before. They have plenty of men/women across from USA & the world that are looking for date/relationship that lead to marriage. It's important to match up someone with similar profile & compatible. She and I shared many similar interests & activities. Both of our family likes us so much. It helps great deal.
    You may need someone (friends) to help you out with many things for improvements. Like from workouts to clothes as make over. You can do it now as it never too late for you. Good Luck for it.

    Posted by KL February 4, 09 03:25 PM
  1. Can Alone and Hopeless meet up?

    Posted by Jane February 4, 09 03:28 PM
  1. I think Hopeless and Alone should go out for a coffee.

    Posted by GregP February 4, 09 03:29 PM
  1. Alone, there is definetly someone for everyone, you just need to reach out. :)

    Posted by BostonLatina February 4, 09 03:42 PM
  1. If you are really that hard up, just go to a bar and sit there by yourself. Dont go there right after work though. Have a few glasses of wine at your house to catch a buzz, and then hit the bar later on in the night That will ensure that people have been drinking and wont be afraid to approach you If you are sitting there by yourself, try drinking something out of the ordinary even if it doesnt taste good. Like a big glass of something with a pineapple sticking out of it or something that catches on fire. That will be a good conversation starter. Make sure it is a strong drink though so when a guy (or girl, you cant be picky at 40) comes over to talk, you wont be nervous. Dont worry, it will work. It might take two or three tries, but it will work. If it doesnt, don't worry, one night stands are fun too.

    Posted by Bud February 4, 09 03:42 PM
  1. Step 1: Learn to love yourself (easier said than done, and the suggestion of counseling is probably a good idea in this regard.) In this way, get a make-over, buy some new clothes, pay up for a personal trainer and join a gym, join a church, find a hobby....make yourself truly happy. If that's too hard, get a puppy.
    Step 2: Learn to think of a potential "date" as just that - a date - not a relationship, not a commitment, just drinks, conversation and dinner. Learn to crawl before you walk.
    Step 3: Figure out what you like to do on your own, and open your eyes to single people who are doing the same things.

    Posted by Bob February 4, 09 03:55 PM
  1. Hmmmm......
    I don't mean to criticize either, but there are an awful lot of folks here who really are trying to put the blame on you.........and there may be nothing you are doing wrong. And that is fact.

    Your story is my story......right down to the bit overweight, no dating of any kind since college and very little of that (count on less than one hand). And yes, it is absolutely concievable one meets nobody since college.....I found that comment insulting......please be open enough Maureen to realize that we all have different feelings and opinions about other people, and that there is nothing wrong with it.

    I found my fiance less than 20 months ago thru events with mutual friends at age 40, and I didn't even like him "that way" for another 5+ months! I had just gotten back into the 'actually leaving the house and doing activities thing' after 5 years of VERY severe voice and back issues that shut down my life. When I "emerged", I could do less than half of the socializing I could before, and was really in a state of grief that I couldn't express myself as the person I had been before because of the new limitations. I was putting the best of myself forward to be sure, but I was feeling that it really wasn't good enough, and that sometimes people were just tollerating me.

    It was when I was in this place in life I met him. He apparently liked me from the start; I didn't actually notice him much the first time, as we were out touring the city with a group of about 16 folks. But he was there at the next couple parties, and I saw him as a quiet, yet funny fellow I thought would be a nice friend, nothing more.
    But he took a "Hope to see you soon" in a e-mail as hope and asked me on what he considered a date....and I didn't. I thought I had a problem, but 2 months and 3 more events later I loved him!

    The point is, while it sure wasn't one of the lowest parts of my life, it wasn't even what I considered even good. I was the heaviest I'd ever been, bad skin from the meds, no muscle tone, voice disappeared if I ate the wrong thing........but it didn't matter to him; he saw the underneath. He's had his issues too, so maybe he saw how I was trying to deal, and liked that. I wasn't looking for anyone for once in my life...I was just trying to reconnect socially with as much of the world as I could. And IT happened anyway....we found each other!

    Keep going out and doing things......and keep trying new things so you can always be meeting new folks, and really get involved in the ones you like. That's how I met him. If there is something you need to work on, then do it.........but don't think that a lack of success in dealing with it is going to stop someone from becoming interested in you. You have my story to know that's just not true. And......don't be afraid to make some moves yourself if it seems like someone you're interested in isn't going to. They can be shy, you know. Make sure they are really available and invite them to something you're both interested in. I did!

    Best of adventures!

    Posted by Tina February 4, 09 04:07 PM
  1. I think its a Waltham thing. I know 2 other people from Waltham with the same (or almost same) problem. I think someone should check the water or something.

    Posted by Travis Brooks February 4, 09 04:13 PM
  1. Bud-
    Love your style. I see a few flags for Hopeless, however: Drinking at home before you go to the bar is an OUI waiting to happen. Then, when you get to the bar, don't leave your drink unattended or you could get Ruffied...or receive 2nd degree burns if your drink catches fire. Jumping in with both feet...you could drown...sink or swim. Meaningless sex might be the way to go, so when your inexperience in relationships becomes an issue, the sex will keep hope alive.

    Posted by wazn't me February 4, 09 04:14 PM
  1. Would you consider meaningless no strings attached sex?

    Posted by dave February 4, 09 04:18 PM
  1. Once you view yourself and your life as full, fulfilling, fascinating - and any potential mate as an accessory to your life - you will have to beat away suitors with a stick.

    I heartily recommend a therapist or life coach to help get you to a happy place!

    Posted by catherine February 4, 09 04:25 PM
  1. I think Jetta #27 had some of the best advice. Just practice talking to people - no dating intent - to get used to interacting with strangers, then you will be ready and comfortable when the time comes to talk to a potential dates.

    Posted by Red February 4, 09 04:29 PM
  1. True!!!!!
    Have a few drinks in your house 1st and you'll get in your happy mood...then go out and get a real unusual "eye catching drink" (guys love to try and figure out what your drinking).....and you'll meet so many guys - you'll be burnt out from talking & laughing with em that you'll just want to go home and crash - then again maybe you'll end up spending the night with one of em (if you want) - go for it and remember to "have fun and enjoy yourself".

    Posted by Anonymous February 4, 09 04:32 PM
  1. I don't say this lightly or sarcastically, but I honestly recommend - along with others helpful suggestions of being active, asking friends to set you up, etc. to go to therapy.

    I went in my late 20's when I was having similar issues, and realized I had alot going on in my head that was keeping me from meeting someone and being involved in a real relationship. I put up walls so thick and so old I wasn't even aware they were there anymore - and then wondered why no knight in shining armor was not climbing those walls. :)

    Along with the other things, therapy will help support you in the process of getting out in the world, letting go of some excuses and embracing a life that is not something you've been comfortable with.

    I came out of my shell, fell in love and got married. And honestly, I'm back in therapy trying not to revert to my habit of climbing into my own little shell (that's natural for me - maybe for you too?). I highly recommend it for everyone.

    Posted by ml2620 February 4, 09 04:45 PM
  1. what do you do for interaction? is there any social activity at all?

    There are warning signs to perhaps needing some professional help.
    1. do you have more than 3 cats? and/or do you have birthday parties for them?

    2. is there a basement involved i.e. of a parent?

    Seriously though. the hardest part of datng is this. Confidence. thats it, thats the big word. I had a bit of ahrd time dating, always picked women who wanted to get married after the first date, or the like. Then i met my perfect one, and once you get that feeling, you get confidence in yourself, and its amazing how many women will ask you out etc after that.
    The trick is to have confidence in yourself frist.
    Now as to the looks issue, It shouldnt be a problem, unless you look like kathy bates and are hitting on george clooney. etc. expectations can be a killer.
    Im not saying settle, im saying get to know someone before you think they arent perhaps prince charming, they may just be everything you need in life and love.
    oh and teling a guy youve never dated before and your 40. TMI , first off why would you tll them your age on the first date. be demure be mysterious, heck its a womans right to lie. Oh and heres rule #1 that you must not EVER EVER EVER EVER EVER EVER EVER break. Do not ever sleep with a man you would like to see again, on the first date. Unless he is shipping out to iraq or something.
    Unless you want to be the booty call of the night dont do it. no matter how much we lie, we will not respect you for it. good luck.

    Posted by Steveh February 4, 09 04:51 PM
  1. Ignore the comments about dnnking to bolster your confidence!!

    There is nothing more unattractive than a drunk/buzzed women alone in public! It looks so sad and desperate!!

    Your confidence must flow from within, and you can do positive things to rediscover your confidence. Be honest about who you are and above evenything, accept yourself! If it is a problem that can be fixed, do it, otherwise, you will have to make a search for someone a goal you put some serious energy into - it is not an accident or apassive activity.

    Posted by Missy February 4, 09 05:17 PM
  1. I recommend eating lots of cheesecake, and letting yourself go!

    It isn't easy. Most guys in your age group have been divorced; the few singles are either unattractive as mates (ex. living in mom's basement), or playing the field forever. If online dating didn't work out, try craigslist (it's free) or yahoo chat. In the "real world" try to increase your networking: Ask friends for help, join volunteer service groups, or just dress up a bit and hang out!

    Posted by Eric February 4, 09 05:21 PM
  1. Steveh, stop being such a prude. This lady is trying to get dates. If she wants to sleep with a guy the first night, so be it. There should be no rules in dating. What if she finds a guy and wants to sleep with him but remembers your advice. No she has to deny the guy and herself. She needs quantity at this point, not quality

    Posted by Bud February 4, 09 05:40 PM
  1. Do you want to go "there"?

    I am 50 years old (a guy) and hardly dated either. No, I am not a virgin, nut-job - or anything of the sort. I've just found that most places people go to "meet" people are simply meat markets ... full of people looking for one night stands. That garbage isn't for me. Don't listen to people who are trying to get you to go to Southie to meet their "ex's"; chances are that their "ex" is full of problems. If you're like me, you don't want someone's "ex" - you only want your own true love. Forget relying on family either; I come from a large family and they've done sh*t to help me. I saw that movie "must love dogs" and wish I had a family like hers. Boston is a drinking town; if you're aren't an "alcy" you are pretty much out of luck.

    Posted by Me February 4, 09 05:46 PM
  1. Hey, Travis of "I think it's Waltham," it's Sasha from Waltham again. You may be on to something. I am happily married, mother, middle-aged, etc., and Waltham is great for that, but I would no more live in a suburb if I were single than live in a retirement village. Maybe our girl should try moving to a more singles-oriented place (though as I said there are great people and activities here). When I was single I lived in Boston and had dates galore. As for the water, we have the lowest lead levels around. Just had to mention that.

    Posted by Sasha February 4, 09 06:25 PM
  1. Hit the gym. I don't say this purely for weight issues, but the endorphins and other effects on your body will do a world of help for your confidence, and boost your self esteem. Then if you can really get going, weight loss will happen quickly and effectively tone you up. You'll be knocking the boys off with a stick!

    3 days a week, 1 hour a day. See if you can pull that off to start!

    Posted by mdminer February 4, 09 07:17 PM
  1. I just wanted to say that my cousin got married last year in her late '60s. She was in therapy for years and years, before she was ready to date. I just feel that if she can do it, there is hope for everyone!

    Posted by Elizabeth in Westford February 4, 09 07:52 PM
  1. OH YEAH!!!! Steveh has nailed it:
    rule #1....Do not ever sleep with a man you would like to see again, on the first date. Unless he is shipping out to iraq or something.
    Unless you want to be the booty call of the night dont do it. no matter how much we lie, we will not respect you for it. good luck.

    I don't understand why women don't realize this is the worst thing they can do. I'd go further and say tell the guy who's going to Iraq to find someone else to disrespect. I've been called old-fashioned, but this to me is HUGE!! Women don't even give guys a chance to get into them before bringing them to the promise land and then they wonder why they're alone.

    Posted by Marj February 4, 09 08:04 PM
  1. "Relax, be yourself, and the quarry will come to you!"

    When I did that, the quarry sure didn't come to me.

    Posted by Jennifer February 4, 09 08:27 PM
  1. "go to the gym...you'l help yourself feel better and lose some weight too..."

    Unless the weight comes off your breasts first, like it does with my body. I have only half a cup size left to lose (and the rest of me still isn't super-skinny so I can't get away with being flat-chested the way Kate Moss can), so I avoid the gym because having a completely flat chest won't make me feel better about myself.

    Posted by Jennifer February 4, 09 08:29 PM
  1. "This may sound harsh, but I'm going to say it anyway: 40, overweight and never dated isn't in a position to be choosy."

    That's stil, in a position to be choosy. If her choices boil down to having sex with a man who turns her off or staying a single virgin, she can still choose to avoid having sex that would be uncomfortable or even painful due to her lack of arousal.

    Posted by Jennifer February 4, 09 08:33 PM
  1. "Meaningless sex might be the way to go, so when your inexperience in relationships becomes an issue, the sex will keep hope alive. Posted by wazn't me"

    WOT?! (And Bud, are you giving her a recipe for self-harm?)

    Meaningless sex could make her feel worse. She's looking for connection, not dysfunction. I can't believe how mean people are to this poor woman. Moderators!

    Posted by reindeergirl February 4, 09 08:57 PM
  1. I like what Jetta said and I may try that myself. I'm 40 too and I have not dated in a long time - at least 4 years. I've had long relationships, but some of them were unhealthy there seemed to be a pattern of me picking the wrong people. So I am not picking the wrong people anymore - I am just not even trying to date. Sometimes I like being alone.I am pretty independent and the work week is usually so busy I'm gone for 12 hours...but the weekends can get hard. But part of me would like to give it a chance again. I admire the poster for being brave and asking for comments. Try Jetta's approach! I am doing that at work with people I used to just breeze by. It helps you feel more connected and confident. I also joined a gym. I am not overweight but I think it is good for general health. good luck!

    Posted by listening February 4, 09 09:01 PM
  1. Hi - I don't think there's anything wrong with your situation or you! I know of several women who are in thier mid-40s', who are very nice women, have a tremendous amount going for them, are very intelligent ,and have never been in a relationship. In fact, each one has barely ever dated, but like you, they do want to start. I have also known of a couple of guys who finally started dating in thier mid-30s. I would recommend that you just get out there and start dating. Even though you have never been in a relationship, you have everything you need to have a wonderful relationship - the same things all those people who are in relationships have! Just get out there in and try to meet people. In the end, once you find the right one, even if it takes a few years, you'll still be better off than so many people who get into the wrong relationshsips and get married sooner, only to find themselves divorced in thier 40s ;-) . It is normal to be nervous when going on dates with little experience, but don't worry. If you are on a date with someone who is interested in you, they won't care at all! Trust me...most likely they will find it flattering. There are also web articles out there that describe some of the things you might find mysterious, or nerve-wracking about the dating process. These may give you a bit of insite on what to expect. ....And the #1 piece of advice - watch out for your first relationship, because you could get carried away, and unfortunately, with the wrong person. Keep your options open, and go slow with becoming emotionally and physcially involved. You can always move forward, but can't move backward. GOOD LUCK and try to have fun in the process!

    Posted by Mike February 4, 09 10:19 PM
  1. Hope you can deal with yet more advice from a guy.

    It's NOT hopeless. I never had a steady girlfriend until I was 34 or so. One approach, and it may not be right for you, is to sit down and think about what the person you want to meet would be like. I'm not talking about loaded or eye candy, I'm talking about how they think, what they like to do, etc. Then pitch your campaign toward that kind of person. This may well make it EASIER to find someone.

    Also, and be honest with yourself, are you depressed or anything like that? ALthough not a fatal flaw, it makes things harder, and you can now get treatment for it. Seeing a shrink and taking antidepressants can help a lot.

    Although everyone says it's true, not all guys are looking for the same thing, either. For instance, I'm not really interested in someone if they're excessively "feminine", heels, makeup and helplessness. I'll bet a lot of other guys feel the same way. And don't be afraid to show off any talents you have. Some of us guys are turned on by smart and talented women. If a guy gets upset because you trounce him at Scrabble, you probably shouldn't be with him anyway.

    Tolerate flaws if they don't mean a lot to you, but don't give up on stuff that's important, at least if you want it to last.

    It's good that you have friends and activities. This means you don't have to get all your social goodies from the one relationship, so it takes some of the pressure off. Find a guy who's got some of these things going on too.

    If you are good at writing and/or giving little speeches, then don't give up on the online dating. From your note, it seems like you might be good at it, although you should be prepared to write many drafts of anything you put up there.

    And skip the alcohol, or at least the second drink. That's a REALLY bad idea.

    Take good care of yourself. It shows that you value yourself. If you do, other people will be more likely to as well.

    Good luck!

    Posted by L February 4, 09 11:35 PM
  1. "It is normal to be nervous when going on dates with little experience, but don't worry. If you are on a date with someone who is interested in you, they won't care at all! Trust me...most likely they will find it flattering...

    "...And the #1 piece of advice - watch out for your first relationship, because you could get carried away, and unfortunately, with the wrong person."

    Good points. Especially watch out for your 1st relationship if he's very very flattered by your lack of experience - he might dump you the morning after your first time if you bleed less than he fantasized about. Sadly, I've heard of this happening after some wedding nights.

    Posted by Jennifer February 5, 09 02:41 PM
  1. Your weight is probably a big factor in this. I am assuming that by mentioning you are a” little overweight” you are really quite a bit overweight. Join a gym and also join weight watchers or something similar. Its a cruel world out there and an older, overweight woman will just not get noticed.

    Hard but true.

    Posted by AlanM February 5, 09 10:55 PM
  1. Your weight is probably a big factor in this. I am assuming that by mentioning you are a” little overweight” you are really quite a bit overweight. Join a gym and also join weight watchers or something similar. Its a cruel world out there and an older, overweight woman will just not get noticed.

    Hard but true.

    Posted by AlanM February 5, 09 10:55 PM
  1. OMG, Jennifer. Seriously?!

    Posted by GregP February 6, 09 12:27 PM
  1. "OMG, Jennifer. Seriously?!"


    Posted by Jennifer February 10, 09 09:39 AM
  1. You are not alone. I am a 32 year old male who is a virgin and has never had a girlfriend as well as having been only on one date in his life. I grew up with little female presence in my life. My mother decided her music career was more important than me so my dad raised me. I wasn't close to my aunts and female cousins(or any family members outside of my dad and grandfather) so any image I had of women came from my father. He did raise me to respect women and see them as equals. But the residue of my mother's inattentiveness has left me distrustful and inadequate.
    For the longest time I did not understand this, but now that I do I am addressing it.

    The point of this is to show you that there are others who have it worse than you in this regard.I openly admit that I have "issues" with women when it comes to establishing deep relationships.That brutal honesty is necessary.

    Some willbe surprised at how frank I am being, but that is no concern. Afterall, many more people are dealing with far worse personal issues than I.

    Prehaps being honest with yourself is what you need to do. Analyze yourself and check for any issues. To cure a disease you first must know the cause of it.

    The comments about fat are absurd. You should lose weight because it increases your chances of living longer, not for aesthetic reasons. There are plenty of men who like average or plus size women. You should just be more willing to put yourself out there.

    Posted by ryan March 8, 09 11:01 PM
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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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