It's possible that you've got an uncommon romance on your hands. Because they're going to see you holding hands with their ex, and remember how nice that felt, and if you think they won't envision you having sex together, you're being naive. In the end, I got about five dates out of it, in exchange for an irreparably ruined friendship. But it's largely a matter of compartmentalizing. It means that it's a bad idea, but that's not the same as "never do it. I don't mean that you can never be happy again after breaking up with someone. Flirting with each other was easy, taking each other's clothes off was easy, and it felt like fate — like absolute magic — and it kept feeling like absolute magic for about a month, at which point I discovered that she was kind of boring, or at least that we bored each other. It's going to hurt even if you say all the nice things you should say — that you're still going to be his friend, that you're going to try not to Instagram this girl obsessively, etc. All of those old wounds stick around, just waiting to be re-opened. Tom found out, and he never forgave me.
I found out about this the hard way, in a similar situation. About a year after she dumped Tom abruptly, leaving him a sniveling wreck, I discovered that I was correct. It means that it's a bad idea, but that's not the same as "never do it. And dwell on the fact that some of your excitement might just come from the taboo nature of this potential relationship, because, like everyone else, you want what's off-limits. Maybe this is your future wife, or muse, or whatever it is that you're looking for. I suspected that she had a low-key crush on me. Now, if you're sure that this is not you, that this is Real Love you're looking at, then what you have to do is tell your friend what's up. This conversation will not go well. Like I said, this is a tough one. You're always going to feel weird when you see your ex, at least a little bit. Over the last couple of weeks, I've been hanging out with a close friend's ex-girlfriend, platonically, after we ran into each other at Starbucks. Of course, that's going to hurt. So what do I do here? Which is that people never really get over significant romantic relationships. There's no two ways about it. Or is she just an attractive person who finds you attractive, too? And I think she wants to take it to the next level, too. The problem is, my friend had a deep relationship with this girl, and I think he's still kind of in love with her. It's possible that you've got an uncommon romance on your hands. You get a new and even prettier girlfriend, or hang out with your friends more, or get into jiu jitsu or knitting. But it's largely a matter of compartmentalizing. Because, again, you're declaring to an old friend that you're prepared to disregard his feelings. Odds are, that's what this is, in which case you should probably just sigh, move on, and hit up your online dating site of choice, where you can find lots of other crush-worthy women. Tom found out, and he never forgave me. He's been on more dates than you can shake a lengthy bar tab at, and he's here to help the average guy step his dating game up a notch — or several.
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