She hangs out with her ex

I think it was Sally who recently pointed out that there are no letters in our "set-ups" category. If you have a set-up-related question, feel free to ask. It's a sad little category right now.

I think we also need a money category.

And maybe a "jealous-about-the-ex category" for letters like this one:

Writing a bit on a whim here, but I'd be interested to hear what you or your readers have to say about this one. The story begins when I met someone I really liked earlier this year, let's call her Marge. When we met, Marge was dating someone else, but soon that ended and we began seeing each other. We've passed the "defining the relationship" conversation and have been exclusive for a few months now and are generally very happy. We spend a lot of time together, have had some great road trips and enjoy hanging out either alone or with our friends.

One negative thing that seems to come up from time to time is the ex, let's call him Jack. Marge and Jack had been friends for some time and had sort of an off-again (mostly), on-again (rarely) relationship with a close friendship in between the periods of dating. Even during the periods of friendship, he was very jealous - and only got worse during the brief periods they were dating. When Marge finally broke things off last year, Jack was very upset and even mistakenly berated one of Marge's other male friends at a social event, thinking he was the "new guy." Marge felt bad about causing Jack pain and tried to maintain the friendship, but eventually that became impossible and they cut off communication for a few months, which was hard for Marge because they shared a lot of mutual friends and the friendship is really important to her. Recently, they've been trying to re-commence the friendship, exercising together and occasionally getting lunch. At this point, Jack still has not been around any time I have been hanging out with their friends and would mysteriously disappear when I showed up at group outings.

Recently, Marge told me that Jack had invited her to attend a wedding with him ("as a friend") out of state. She mentioned that he really didn't want to go to the wedding alone, and he told her none of his other friends could make it. Not wanting to seem overly controlling, I only let Marge know I thought this was a bit weird, but I did not say I thought she shouldn't go (even though it made me very uncomfortable, I told her I had no rational reason why she shouldn't go). We both agreed that it would make the most sense for us to see how he acted when I was around, since that might give some indication about whether he intended to really be a friend or was just using this as a way to stay close to her. Well we all hung out at a party this weekend, and it was clear he was extremely uncomfortable around me. I am an approachable person and talked to everyone at the party, except for Jack. To me it seemed like he avoided engaging in any sort of conversation with me.

So now I am really uncomfortable. I am in disbelief that someone who appears to have these continuing issues with Marge would ask her to go to the wedding, and, to a lesser extent, I am upset that she'd agree to go with him. I am 100% certain that Marge would not cheat in any way and pretty sure he wouldn't try to make a move, but some part of me still just feels really uncomfortable with the situation, even though I can't rationally explain it. What should I do? Put my foot down and say it's a dealbreaker or suck it up and let them figure it out for themselves? Am I uncomfortable because I have issues with trust or because this is something inappropriate (i.e., going to a wedding with a recent ex)? To make it trickier, I still haven't told Marge I am uncomfortable and the wedding is soon. What should I do?

– Uncomfortable in Brookline

UIB, you don't have weird trust issues. She's in the wrong here.

You may be out of luck for the wedding depending on when it is. It's not fair to tell her a week or two before the event that you’d rather she not go. But when the wedding trip is over, it's time for a talk. You don't have to be the super cool boyfriend who shrugs when she's at the gym with an ex who still loves her. You do have to be honest boyfriend who says, "Just exactly what are you trying to do with this guy?"

Many letter writers say, "I trust my partner -- it’s the ex/friend/gym buddy I don’t trust." But that's not really true, is it? Your issue is with Marge, not Jack. And my issue is with Marge, not Jack. If Marge is really worried about Jack, she should set major boundaries with him so he can figure out that there's no future and get over her. And if Marge is worried about her relationship with you, she should go out of her way to make you (the new boyfriend) comfortable. Right now she's being bad to both of you (unintentionally, I hope).

When the wedding is over, sit her down and tell her that you’re not loving this -- because no normal person would love this. Ask her why she thinks this is good for Jack. And ask her what she wants her relationship with him to be in the future. If she really wants a true friendship with him, she shouldn't be going to weddings with him. She should be going out of her way to show him that she's just a friend.

If she can't cut her close ties to Jack, well, there are things to consider. But know that you're not in the wrong for having weird feelings about this. It's time to disclose them.

– Meredith