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This is going to sound weird and conceited and awkward, but please bear with me. I’m a 28-year-old man, and from what I’m told, I’m a “catch”. I’m well-employed, fairly handsome, and what my friends call “accidentally charming”. I’m incredibly lucky for everything I have in my life, so I’m not complaining about myself.

My problem? I can’t date normally, because the women I date get attached and I don’t have the heart to let them down. This has happened my entire life. There are women (who were then “girls”!) from fifteen years ago on through present day who consistently call me the one who got away, and it makes me feel awful. I’ve never once even briefly dated a woman who hasn’t come back days/weeks/months/years later to tell me that she “lost me”.

It makes me feel terrible, so I stick around in bad relationships. I know I do it, but I can’t bring myself to ruin another person’s feelings until I’ve been there long enough to start hating myself and my life more than I care about her. I’m in this cycle now – my current girlfriend is a sweet, kind, fun woman who’s utterly dedicated to me and who I can’t see myself with long-term. She’s been through many bad relationships, and to her, I’m “The Guy.” But I’m almost thirty and I know I don’t want to spend the rest of my life with her, so every time I’m with her, it’s bittersweet. What can I do to break this cycle and end relationships without lingering feelings of guilt?

Jay

Thirteen years ago, I dated somebody casually for about a month. Zoe. Lovely woman. Smart. Nice. Great sex. Different senses of humor and sensibilities. I didn’t see a future with her, per se, but I was definitely enjoying myself and thought she was, too.

Thanksgiving rolled around and I recalled that Zoe had lost both of her parents separately in the past year. As a guy whose father died at a young age, I was particularly sensitive to this issue, and even though I wasn’t her boyfriend, I called her on the holiday to see how she was holding up.

The second you don’t see yourself with your girlfriend in long-term, break up with her and let her find another guy who does.

I was just doing what nice, sensitive guys do, right? What I didn’t calculate was that, in taking that intimate emotional step, I pretty much induced this woman to fall for me. I was no longer the boy toy; I was suddenly acting like a boyfriend.

That’s why the second the conversation was over, I knew I had to break it off. And I did. In person. Upon which she said:

“I think this makes me like you more than I already did.”

“I hope this doesn’t mean we can’t have sex from time to time.”

Yes, this was one story in which doing the right thing led to a positive outcome. But the truth is, Zoe couldn’t handle our FWB relationship. We only got together one time after that.

I thought of this story when I read your letter, Jay, not because I doubt that you’re a “catch,” but because I find it almost amusing that you don’t know how to break this cycle.

If you’re going to feel guilty about anything, let it be that you’ve been wasting lots of women’s time under the guise that you’re too “nice” to hurt them.

Don’t get me wrong: you’re not alone. I routinely coach women who have trouble breaking things off from men. More commonly, I field complaints from women who date cowards like you who don’t have the spine to break up when you’re never going to marry her.

So there’s your answer, Bittersweet Jay.

The second you don’t see yourself with your girlfriend in long-term, break up with her and let her find another guy who does.

Doing so makes you nice. Not doing so makes you cowardly.

If you’re going to feel guilty about anything, let it be that you’ve been wasting lots of women’s time under the guise that you’re too “nice” to hurt them.

Sorry, but that’s not true. You’re just being selfish.

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