Q: I've been with my boyfriend for 2 years. He's great in many ways - cute, funny, good to my kids, hardworking. Our chemistry is off the charts. However, one thing continues to bring me down.
He feels the need to share SO much (everything ... even sexual escapades in a campground) about his past loves. If we go somewhere new to us, he wants to tell me all about his last trip there with whomever he was with before me. If a song comes on and it reminds him of when he was trying to get over some other woman, guess who gets to hear all about it? Me!
Recently I blew up at him because we were in the grocery store and he saw an unusual item that another woman had used to make him a fabulous dinner. Well, I already heard that particular story in detail before, so as I saw him pointing out the item and getting ready to "share," I exploded and stomped off to the deli case. This caused a huge fight (again), as I have told him that I don't want to hear any more about his former conquests. I would never do that to him. I think it's hurtful and unintelligent. He says it's his history, what makes him who he is, and he's with me now and that's what matters! Please, can you offer me any advice?
- L.B., Amherst

A: He is either insecure and wants to make you jealous, or he hasn't gotten over any of his past relationships.
I'm betting on insecurity here. He wants you to know that he can have other people, but ultimately is choosing you. After two-plus years together, these things are not necessary to bring up, and he needs to cut it out. I understand that an occasional conversation might require mentioning an ex, but the instances you've listed are ridiculous.
He keeps doing it because you keep reacting to it. Sit him down and calmly tell him one last time that you will no longer listen to him talk unnecessarily about his ex-girlfriends or past sexual encounters. If he does it again, ignore it and change the subject. It will be difficult, but once he sees that he's no longer getting the jealous reaction out of you, he won't find any reason to keep doing it.
However, he does come across as really immature. If he feels the need to bring up his past in order to reassure himself of your love for him, he's not ready for a serious commitment.

Breaking the news

Q: How do I tell a long-term boyfriend from 15 years in the past, who still hopes for reconciliation, that I'm seriously involved with someone else? I made the mistake of staying in occasional touch via mail and email over the years in a platonic way while I was dating others. Now I really need to terminate contact, but I think he will be crushed, which is why I haven't said anything yet.
- S.D., Buffalo

A: Just tell him the truth and stop talking to him. He's a grown man, his heart will mend, he will find another woman, and you will both go on with your lives. If you've known that he wanted you back all this time, it was selfish of you to lead him on by evading the truth about your current situation.
Do the right thing and do it soon. A simple message of "I've enjoyed keeping in touch over the years, but I'm in a serious relationship right now and I don't think it's appropriate that we keep in contact" would suffice.

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