Q: Dear Meredith,
I'm a longtime lurker. And since I can't turn to my friends for advice, I thought I'd turn to yours. A few months ago, my best friend from childhood, "Stacey," got married. I was her maid of honor. Stacey's parents have been separated since we graduated high school but just haven't divorced yet (financial reasons). They live apart but in the same town. Anyway, at the wedding, I had more than a few drinks (after all, it was open bar and my job as MOH was to lead the fun). Stacey's dad, "Bob," and I started talking. A lot. When we were teens, Stacey's friends and I used to joke that her dad was hot. Well, wow. He actually is. There was a connection. Needless to say, it was awkward around Stacey's mom since she used to make us cookies all the time and here I am flirting with her almost ex-husband. He's my best friend's dad. It's weird, I know. But hey, at least I didn't throw a shoe! Anyway, after the wedding, Bob and I started dating. We didn't tell anyone. He makes me laugh, has great taste in wine, and well, let's just say that there's some benefits to dating an older, more experienced man.
I've wanted to tell Stacey but there really is no easy way to say it. Her parents are separated and are going to divorce, but it still really bothers her. Bob wants to tell her,
but I've been taking an "I'll deal with it tomorrow" approach. But here's the real problem. Bob has Red Sox season tickets. He has four seats for Opening Day. He wants to invite Stacey and her husband. And me. Can we say awkward? I know I need to tell Stacey and I certainly don't want a scene at Fenway. (I mean, it's the Yankees!). How do I tell her? I don't want to ruin anything. I am enjoying my time with Bob. I like him and I want to keep seeing him. I also don't want to lose my best friend. Do I just show up at the game with Bob and hope she doesn't flip out? Do I talk to her ahead of time? Does Bob tell her?
– I'm In Love With Stacey's Dad
A: You are not allowed to go to this game, IILWSD. You are certainly not allowed to surprise Stacey by showing up at Fenway Park on the arm of her dad. I mean, even if Stacey knew about your relationship with Bob and was cool with it, she might not be ready for a double date. Please put yourself in her shoes.
Before you sit down and tell Stacey that you're in line to be her stepmom, please think about whether this whole Bob thing is worth it. Can you really see yourself with him in five or ten years? You don't have to know for sure whether you want to be the next Mrs. Bob, but you do have to be honest with yourself if this is just a fun fling. Because if it is, you must end it -- for the sake of everyone's sanity.
But if Bob is worth the risk and you do want to stay with him, tell Stacey as soon as you can. Explain to her that you understand how weird this is and that you're confused and looking for guidance. Ask her what she needs you to do to make this work.
And again, whatever you do, don't spring this on her at a game. Opening Day against the Yankees is stressful enough on its own.
Readers? Is she going to lose Stacey? What are your thoughts about Bob? Could you deal with one of your peers dating one of your parents? Discuss.
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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 new novel about complicated relationships. Follow Meredith here and on Twitter. Love Letters can be found in the print edition of The Boston Globe every Saturday in the G section.