Skip Nav

Ask a Wise Guy: How Do I Get His Ex Out of the Picture?

Conventional Wisdom is a different kind of advice column. Your questions will be answered by people from all walks of life rather than by advice experts. Today, a person who likes to think of himself as a wise guy will offer some common sense advice. You can submit questions here.
Today's Question:

My boyfriend and I have been dating for about a year. Things have been going very well, except for something he can't seem to let go of. Two years ago he and an ex broke up, and ever since he and I started dating she continues to devote attention to him. It never appears to be romantic, but she's always offering to do him favors, asking him to play with her dog, texting/calling/Facebooking. As far as I know, he doesn't respond all that much.

But that's the problem. By not responding, he has not made it clear that there is no room for her in his life now. So the other day I told him that if he wanted to move forward and have a future with me, he needed to make it clear to her that the past is in the past.

He agreed, but now I'm playing a waiting game. I don't want to nag and ask him when he is planning on having this conversation, but I also want to know when it takes place. She has continued to contact him and he continues not to act.

I'm beginning to wonder if I'm fighting a losing battle. Could there be a deeper reason he's dragging his feet, or is he just being passive aggressive? Am I crossing a line by putting pressure on him? Or should I be drawing a line, and saying enough is enough?


Sick of the Ex. To hear what a wise guy has to say,

Dear Sick-of-the-Ex,

Wow, this is a tricky one —in fact, navigating exes is a complicated (but necessary) dance in any relationship. I’m also a little confused about what your boyfriend wants. If he really isn’t responding to her “all that much,” then it seems like the message is pretty clear that he’s not interested in spending time with her — and so the whole situation shouldn’t be a threat to you (and you should back off). On the other hand, if he does sometimes call/text/play with her dog, then it seems that he still wants her to be part of his life, in which case there needs to be a lot more clarity between you and him about what’s OK and what’s not.

Here’s where it gets tricky: if you prefer that he have no contact with the ex, and he wishes to maintain a friendship with her, then one or both of you will have to compromise what you want.

Reading between the lines of your letter, I’m sensing that you don’t feel as secure as you should in the relationship. If you’re feeling threatened by a few phone calls and text messages, then I think there’s something deeper going on here that needs to be addressed head on. I think you should have a heartfelt conversation with him explaining why you’re not happy with the situation (rather than telling him what to do), and then figure out together how to deal with the ex. This seems like a better way to handle the situation than “putting pressure” on him, and giving him ultimatums about your future together. If he really cares for you and respects your feelings, then I’m hopeful that you can come to a solution that works for everyone.

And if that doesn’t work, you should go her house and duke it out Jerry Springer style. Guys like it when chicks fight over them.

All the best,

A Wise Guy


Latest Love
Looking for the perfect gift this holiday season? Order our POPSUGAR Must Have box now >>