About half a year ago, I briefly dated basically the most beautiful man—picture Ryan Gosling's bigger, stronger older brother—and had the best sex ever. (I'm a straight woman, BTW.) It ended because he didn't want to get serious but he has expressed enthusiasm for hooking up again. I think about him during sex all the time, but I feel conflicted about it—maybe it keeps me from moving on? So should I try to stop thinking about him? Or should I sleep with him again? I don't know how much I'd enjoy sex with him since I'd be hoping he'd fall in love with me.

I guess I just hate the feeling of leading a second-choice life. It doesn't feel fair to my current sex partners, great people who all are first choices for someone, but I know we can't all marry the most beautiful person we've ever been with. It's just that I always thought I'd end up with someone who I think is beautiful. I'm 32 now and no one's made me feel that way in a long time—except a stupid sexy guy who didn't want to get serious.

Does he deserve to be immortalized in my sex fantasies? It feels like living in defeat but it makes orgasming very easy.

Thinking With Portals

My response after the jump...


First off, TWP, I can't believe you would send me a question like that. This Ryan-Gosling's-bigger-stronger-older-brother stuff—you seriously expect me to take your word on that? A courteous person would've sent pics from multiple angles.

I will look for your followup email. My advice in the meantime...

I don't generally subscribe to the fuck-em-and-get-em-out-of-your-system theory. If you fuck this guy again, and fuck him on his terms (hooking up only, no dating or romance), you're unlikely to get what you want—that is, he's unlikely to fall in love with you, ask you to marry him, and impregnate you with scores of muscular little goslings—and you'll continue to obsess about him, at least over the short term. But you're not fucking him now and you're obsessing about him, right? So a case could definitely be made for fucking him since you're going to obsess about him anyway.

So fuck him, I say, from multiple angles.

And who knows? It's possible—it's unlikely, but it's possible—that he'll be ready to "get serious" at some point and, hey, if you're the person he happens to be fucking when that day comes... maybe he'll get serious about you. It's also possible that this relationship ended so quickly that you were incapable of seeing his flaws. People we date briefly often seem perfect; people we date for months or years—or just hookup with for months or years—rarely seem perfect. He may be no less beautiful after you've fucked the shit out of him for two or three years, TWP, but by then you'll be acquainted with some of his less attractive qualities and you'll be able to move on, no longer obsessed, with this boy him safely tucked away in your solodex.