I broke up with a girl who wasn't hot enough for me. That's specifically why I broke up with her. I tried for my whole life to not be that kind of guy. I treated her carelessly because she wasn't that important to me. I would be self indulgent and rude and disrespectful. I would take her for granted and not pay attention to her, and it made her cry, but she put up with it anyway. She's perfectly attractive, but not in the obvious way, which is what I want. I can't get away from wanting that, no matter how hard I try. I love her still for everything she has done for me, but I don't want to date her. I feel guilty because I don't want to abandon her as a friend, because she is still a pillar of support that I have not had, and have needed to have, for a very long time. She's the first girl I ever fucked, and I'm the first guy she's ever dated. She is 28 and I am 24. We have known each other for one year. In general is it more important to have good friends or have someone to love? Is it a bad idea to maintain my relationship with her while I pursue other women? Would it be better to end all contact? What is a man who is pathologically worried about being an asshole to do?

Must Remain Anonymous

My response after the jump...

So... you were a virgin at age 23 when you met this woman.

Hm.

I'm guessing that you're not conventionally attractive yourself, MRA. You're attractive, of course, just not in a conventional sense. You're attractive in the same way that, say, your ex-girlfriend is attractive. Perfectly attractive, just not obviously attractive. Not hot.

But what you want—what you feel entitled to—is a woman who is attractive in obvious ways. A woman who is objectively hot. And you may get one. There are lots of obviously and conventionally and objectively hot women out there with guys who aren't, objectively speaking, anywhere near as hot. Helps if the dude's a billionaire. But a word of warning: If you had to wait until age 23 for a woman to come along who was 1. willing to fuck you and 2. willing to put up with your shit, MRA, the wait for a hot woman who's 1. willing to fuck you and 2. willing to put up with you shit could be a long one. But you can live in hope.

What you can't live in, MRA, is some sort of alternate reality where you've been anything other than a complete and total asshole to the woman you've just dumped. All that worry—all of that pathological worry—about not being an asshole was for naught: you've been an asshole, a complete and total asshole, a frothin', flamin', flippin' asshole. You treated this woman terribly. You emotionally abused her for the not being something she wasn't when you met her (and something that you're not either): conventionally, objectively, and obviously attractive. You weren't obligated to stay with her forever, MRA, but you were obligated to treat her with kindness and consideration. You were an asshole instead—you went out of your way to be cruel—and that was unnecessary and uncalled for.

Under the circumstances, MRA, I think it's best to end all contact with your ex. I mean, it's nice that you're willing to keep her in your life in order to get the support that you need, support that she's willing to provide, all the while providing her with nothing in return—no, wait. That's just more assholery. Cut her from your life. It's the only decent thing to do. It may the only decent thing you've ever done for her.