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Q I’m a 29-year-old male, straight, fairly attractive and with a pleasant personality, etc. But—there’s always a but, right?—I’m a huge whoremonger! I lost my virginity at 21 to a sex worker and I’ve been whoring ever since. I’ve never had a girlfriend. None of my friends or family know about this secret side of my life. They think I’m secretly gay or just lazy. I see someone once a week or every other week. Some of these women I’ve been seeing for five-plus years. I get tested for STDs every two to three months (in my eight-plus years soliciting prostitutes, I’ve never had any health issues). And we are not talking about anything crazy, just plain old penis-in-vagina sex for money.

So now I am almost 30. Most of my friends are married, lots of them have kids. And I have nothing to show for myself in terms of my love life. I tried online dating, and I can get dates easily. But I hate dating. Also, especially with my sexual history, I just feel bad about misleading these nice “normal” girls you meet on eHarmony. But I don’t want to die in utter solitude. So, any suggestions?

A Um, yeah, stop having meaningless sex with prostitutes. Plus, you’ve got to start addressing the fundamentally flawed way you view sex. It seems like, for you, the only real sex is sex that has some sort of illicit edge, and the idea of actually doing it with a “normal” eHarmony woman is too pedestrian and boring to even contemplate. That’s a problem for someone who ultimately wants to end up with a wife and kids. It’s also patently absurd. By maintaining a prostitutes-only sex life, you’re basically chickening out on developing an emotional attachment with someone. And emotionless sex is never really as hot as the kind where real people and real feelings are involved. It may seem hot in the moment, but eventually that hollow, what-the-hell-did-I-just-do feeling sets in. Oh, and using your sexual history as an excuse for not pursuing normal dating opportunities isn’t going to cut it. You either want to change your ways or you don’t. Worry about how you’re going to explain your lost decade to a potential mate later on; right now, an awkward first date with a run-of-the-mill woman is exactly what you need.

Q I’m a healthy, relatively attractive 41-year-old woman. I recently separated from my husband of nearly ten years and have just begun dating again. I met a man online who is also divorcing (after more than two decades). We hit it off and the sex is great. Problem: He’s a dater, meaning he’s seeing a couple of other people in addition to me. We’ve talked about it. He knows it makes me uncomfortable. I guess I’m asking your advice here, because the situation is causing me a lot of anxiety. When I see him, things are fine, but I’m hungover until the next time we go out (like, once a week). I don’t have a lot of dating experience, so I’m asking for your take on this. There’s part of me that says he’s worth sticking around for and another that says I should cut him loose. What do you think?

A If your marriage has just recently ended, then why aren’t you being a “dater” too? There’s no reason to completely cut this guy loose, but I certainly don’t want you sitting at home waiting for him to call, either. I get the feeling that you’re trying to take a shortcut through the dating process by latching on to the first guy you have a genuine rapport with. But it’s far too soon postbreakup to start settling down again. You should be filling your time in between dates with this guy by meeting other people. The last thing you need is for someone to treat you like a safety net—and chances are he’ll be a lot more attentive when he realizes that you’re not looking to take things too quickly.

Send letters to Jamie Bufalino c/o Time Out New York, 475 Tenth Avenue, 12th floor, New York, NY 10018, or send e-mail to sex@timeoutny.com.

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