When Your Ex-Boyfriend Starts Dating Women

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Social Q’s

I am a gay man in my late 20s. For a few months, I hung out with this young guy who had just finished college. We had a strong sexual connection but not much else in common, so the relationship didn’t last. I was pretty disappointed. Now I see that he is going out with a woman. I don’t know much about relationships, but I know when a guy likes having sex with other guys. And the woman he’s going out with is a friend of a friend. Should I tell her about my relationship with her new boyfriend?


I love to put people in boxes. (It’s one of my worst qualities.) Still, they give me the illusion — albeit false — that there is order in our chaotic world; so I cling to them. But one of the things that’s impressed me most about young people, these days, is their bravery in foregoing labels (and boxes) when it comes to gender and sexuality in favor of more honest self-expression. Who knows where all this fluidity may lead? But let’s hope it’s in the general direction of greater fulfillment.

Just because your young man enjoyed sex with you doesn’t mean he can’t enjoy sex with women. Abandon the notion that you are somehow “saving” the woman he is now seeing by telling her about your relationship. There is no evidence that she needs saving. To me, speaking up would smack of vindictiveness masquerading as white knighthood. Don’t be that guy.

Still, I get your disappointment about the relationship not working out. But on the plus side: It points to your desire for a deeper connection, which is the first step on the road to having one. Until Mr. Right appears, I suggest an old-fashioned remedy: the breakup film. My go-to was always “Sense and Sensibility” (the Emma Thompson version, please). Honor your feelings of loss, but don’t try to scotch your ex’s new thing.

An Epistolary Oops

For almost 40 years, I kept in touch with a college friend through letters. (Real ones — on paper, with stamps!) There was no romantic overtone to our friendship. A few years ago, he wrote that he had a terminal illness. As it progressed, I heard more from his wife, whom I didn’t know, than from him. Frequently, she wrote things I would have preferred not to know, but I think it helped her having someone to confide in. After my friend died, she wrote that he had kept my letters and she had read all of them. I was deeply offended. I waited six months, then wrote that I was upset that she had violated my privacy. I never heard from her again. Was I wrong?


Your friend’s wife erred in reading your letters. You mention that there was no romantic cast to your friendship, but that doesn’t mean you didn’t confide intimately in him over the years. She should have returned the letters or destroyed them. Still, people who are grieving grasp at any and all straws within their reach. I turned my parents’ house upside down after their deaths, hunting for unspecified clues and violating their (and other people’s) privacy right and left.

So, I wish you could have exercised the same kindness during the widow’s mourning that you did when she provided uncomfortable details during your friend’s final illness. Her intention was probably to connect more deeply with you as someone who cared for her husband. That doesn’t excuse her invasion of your privacy, but it does explain it in more sympathetic terms.

Second Time Around

My 32-year-old son is about to marry for the second time. His first wedding, in 2014, was a blowout destination affair for 120 guests. It cost the bride’s family and ours a ridiculous amount of money. They separated four months later. His second wedding is going to be very small (immediate family only). Is it appropriate to send a wedding announcement to close friends and family? It’s awkward because some of them don’t know he divorced. And we don’t want to look as if we’re hinting for gifts. We just don’t want people to be surprised when his new wife turns up.


Of all the brilliantly funny lines uttered by the brilliantly funny Carrie Fisher, one of my favorites was her explanation of her 11-month marriage to Paul Simon: “Short people, short marriage.” It is perfectly appropriate for your son and his bride to send wedding announcements to family and friends. His first marriage was a mistake; we all make them. No need to shroud his (hopefully better-considered) second marriage in secrecy.

You may receive a few calls from folks who are curious about the first wife, and they may receive a few gifts. To the first group, say, “It didn’t work out.” To the second: “Thank you.” We can’t live our lives in fear of people on the hunt for venal motives. A wedding announcement calls for gifts only to people who want to make them.