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Was breaking up the best decision?

Maybe I could have given it more time

Love Letters

Love Letters

Q. Yesterday I broke up with the man I’ve been seeing for the past 2½ months. We’re both in our 40s. I have two children I share with my ex. This man doesn’t have kids and has never been married.

We met organically when we kept bumping into each other on the streets of Brooklyn. That’s quite unusual, so it was hard not to become curious. One day he stopped me and asked me out. It was great for some time, meeting every four to five days for dinners, drinks, and sleepovers. Texts a few times every one to two days. Sharing music, movies, things we like. We seemed to have a lot of tastes and interests in common.


The thing is, the relationship didn’t seem to be advancing the way I wanted it to. The frequency of everything remained the same. I wanted the intimacy to grow, the connection to improve, and it didn’t feel like that was happening. I wasn’t feeling comfortable and relaxed. Instead, it started to feel frustrating and superficial.

The last time we went out felt uninteresting. He has the tendency to talk to everyone everywhere we go, and that last night it was too much. The conversations were focused on other people around us, instead of about us or between us. It was boring to say the least. It was also my birthday, so my expectations were higher. He will be perfect for someone who can appreciate that type of extrovert.

I explained myself through text the following morning and wished him the best. I realize I could have done that better; I think I was pissed. He seemed surprised at first but then basically said we are obviously not a match after all. Our text conversation could have been a call and maybe things would have been different. But I don’t know, maybe that felt too vulnerable, and I was already half out the door, and he didn’t stop me.


I think I did the right thing for me, but the loss of what could have been is still painful. Being intimate with someone develops all kinds of feelings in me that I can’t just switch off instantly. All the could-have-beens that will no longer be. My question to you is: Did I honor myself by deciding how I didn’t want to feel with a partner, or did I jump ship too soon without giving this relationship a proper chance? Was I too afraid of being vulnerable in a conversation, and maybe not being met with reciprocal feelings?


A. It doesn’t sound like you initiated this breakup because you were scared to get close to someone. Had he asked deep questions, you would have answered. Had either of you been desperate to see each other more often, one of you would have asked.

Yes, an in-person breakup would have been a good idea (please learn that lesson), but it wouldn’t have changed who he is.

It’s simple: You weren’t compatible.

Why do you feel so unsettled? It sounds like you’re experiencing buyer’s remorse, but for a breakup. Many big decisions are followed by a period of overwhelming doubt, even if you did the right thing.

Give yourself time to get over the second-guessing and try not to change the story. Don’t pretend he had qualities he never showed you.


Make room for loneliness and disappointment. It’s sad to look at a phone and see no texts, or to have a week without romantic plans because the person you were dating is no longer there.

Also allow yourself to be bummed about the anticlimactic end to a really great meet-cute. I mean, who meets on the streets of Brooklyn theses days? What are you, Harry and Sally? It’s too bad it didn’t lead to cinematic bliss. But it’s a good reminder that origin stories don’t matter much. Maybe you’d be better off connecting with someone on an app.

Let yourself feel OK about moving on.



Not every great person is a great match, and it’s perfectly OK to acknowledge that and to feel a pang of “what might have been” as well.


Exactly what were your expectations for a birthday celebration with a guy you literally met off the street, whom you had been dating less than 90 days? I think you need to lower your expectations.


Did you mention that you’d like to spend more time together or were you just assuming he would know? Maybe he assumed you would say something, especially since you’re the one with two kids half the time.


You ended it when you saw you weren’t going to go the distance. Not dragging things out is a good thing.


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