Take her out to the ballgame?

She’s hot for her best friend’s dad, and he wants to take her to Sox with . . . his daughter

By Meredith Goldstein
Globe Staff / April 9, 2011

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Q. 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, and 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?


A. You are not allowed to go to this game. 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 10 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 the ballpark. A Yankees game is stressful enough on its own.



For the love of God, what are you doing? I don’t care how hot Bob is, you are so wrong, wrong, wrong to be doing this. POOHBEAR44

Can you say Daddy issues? He’s HOW MUCH older than you? And they’ve been “separated’’ for how long, without divorcing? Good luck surviving the drama vortex you’ve created around yourself. THETINMAN

When I was in high school, I had two BFFs — Dana and Cathy. After graduation, Dana started dating this guy, Scott. Cathy started dating Scott’s dad. Cathy ended up marrying the guy. Dana and Scott were in the wedding. Sometimes these things work out. But you have to tell Stacey. Before the game. If it doesn’t go well, ping me. I’m happy to upgrade my seats. LILY

Today I can write “Meredith hit this one outta the pahk’’ without embarrassment.


If this is for real you are a lousy friend and Bob is a crappy Dad. Do you really think double-dating is a peachy-keen idea? Stacey’s entire world will be thrown into chaos. She will rethink every moment of her past friendship with you, and she will question her entire relationship with her father. And I won’t even talk about her poor mother’s feelings. Break this off with Daddy-o, remove yourself from Stacey’s life for her sake, and get thee into intense therapy STAT. You have more issues than all of us armchair psychiatrists could handle. THEREALJBAR

If by some chance you think it might be serious, you’d better check in with “Bob’’ first to be sure he agrees. (I’d guess not). Then get out of the situation as quickly as you possibly can. The big question next is, do you ever tell “Stacey’’? If you decide to, please do it somewhere private and give her plenty of time to react, respond, and hopefully forgive. In any case, stay away from the game. NEEDCOFFEE

True story: Shortly after my parents divorced, my Dad asked me if it would be OK if he dated my best friend (I was in college at the time). Here is what I did: I FREAKED OUT! In NO WAY did I it find it cool. Needless to say, I said NO! (actually NO, NO, NO, NO, NO!) and then had to blind my mind’s eye. Bleak! To my Dad’s credit, he never said a word about it after that and never approached my always-around BF. Years later, he met and married a wonderful woman who is only slightly older than me (she is my hubby’s age) and he is blissfully happy.


Edited and reprinted from Meredith Goldstein can be reached at She chats online Wednesday at 1 p.m.