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What went wrong this time around?

I thought he wanted to reconnect

Love Letters

Love Letters

Q. Recently I received a message from a guy I dated three years ago. We only dated for about two or three months. From what I remember, it ended amicably because we agreed there wasn’t a strong romantic connection. However, we did end up having a physical one. We hooked up a few times during that period and went our separate ways. We hadn’t seen each other since.

Then he friend requested me and messaged me on Instagram, saying he wanted to “reconnect.” When I asked him what he really meant by that, he said, “I remember we had fun together and that we did get kind of hot and heavy ... but I just wanna go out and see what happens.” We hung out and I was expecting him to maybe talk about our history and what we’ve been up to since then, but of course we hooked up again. The second time we got together and hooked up he seemed a little hot and cold. Before he left my apartment he said, “I don’t really think we should see each other anymore like this.”

He used the classic “it’s not you, it’s me” line. I know it was a huge mistake agreeing to meet up with him, but should I ask him to explain why he thinks this all of a sudden? Or should I just move on and make peace with it?



A. I think you know what happened here, right? He wanted to hook up with you, which is exactly what happened. Even if he enjoyed himself, he wasn’t motivated to try for more.

If you’re looking for a deeper emotional relationship with someone, it’s better that this ended now. You could have played this game for another three months, leaving you wondering why you repeated the experience for so much time.


Before you go into a deep hole of rejection and shame for making a mistake (for the record, it doesn’t sound like a mistake; it was a fact-finding mission), please know that it doesn’t seem like you were very interested in this man either time you went out. Part 1 was about sexual chemistry and it ran its course. As for Part 2, well, did you ask him questions about what he’s been up to? Did you laugh at his jokes? Were you having a good time? I get the sense you were going with the flow and trying to figure out his motives, but it doesn’t sound like you felt a great pull to him as a human.

My guess is that it’s not him or you, it’s just a brief experience that’s a step along the way. Feel free to move on.



He was between partners and remembered all the “fun” you used to have, so he looked you up and — voila! — still fun. A couple of times. If you don’t like doing this kind of thing, then take it as a warning and move on.


It was a booty call and that’s it. I wouldn’t be surprised it he reached out to all of his former flings to see who was available.


He pretended to be open to the possibility of a relationship in the hopes you would hook up with him. You pretended to enjoy the idea of a hookup in the hopes that it might lead to a relationship with him. Just use this as a learning experience and don’t make the same mistake (with him or anyone) next time. Not quite the same scenario but for some reason all I can picture is Jon Hamm and Kristen Wiig in “Bridesmaids.”



Don’t ask him for an explanation (the mysterious “closure” that some people seem to need). He wanted sex. He got sex. He’s done. Nothing more to see here, just move on. But don’t continue to interact with him on social media.


Send your own relationship and dating questions to loveletters@globe.com or fill out this form. Catch new episodes of Meredith Goldstein’s “Love Letters” podcast at loveletters.show or wherever you listen to podcasts. Column and comments are edited and reprinted from boston.com/loveletters.

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