Skeleton Closet

I'm a 34-year-old man who's never had a girlfriend. I've had sex fifteen times or so, all with prostitutes, except for one drunken one-night stand with a stranger I met in a bar. I spent my 20s drinking, to the exclusion of pretty much all other activities outside of work. Although there's nothing physically wrong with me, I believed that no woman would ever consider sleeping with me (and this was a self-fulfilling prophecy for sure, given the absolute mess I was). It followed, then, that the only way it was possible for me to have sex was to pay for it. This was insane, but I believed it unquestioningly.

I got sober in 2000 and have spent the last four years sober and getting the rest of my life (financially, emotionally, etc.) into some kind of order. Things have gone reasonably well, and I am planning to start dating soon.

Here's my question: How, and when, do I tell a potential sexual partner about my unusual and possibly unsettling history? I haven't had intercourse in over five years, and got myself tested for HIV eight months ago; I am HIV-negative and have never contracted any STD. It seems to me that the responsible thing to do would be to inform any woman who was considering sleeping with me that my sexual history consists almost completely of intercourse with prostitutes. I strongly suspect that having been with a prostitute even once would be an immediate show-stopper for most women, though, and the explanation-that I honestly believed that was the only way for me to be with a woman-isn't going to help clear things up. I want to be in a normal, healthy relationship with a woman, so how do I tell her that I've (a) never been in a relationship and (b) had sex with many prostitutes? What do you think I should do? I really want to do the right thing.

-Unsure How to Tell

A:

First of all, Señor Unsure, you've got to give yourself a break. Quit being so hard on yourself. Self-deprecation can be charming; self-loathing has quite the opposite effect. It sounds like you've done an excellent job of overcoming obstacles a lesser man might have found insurmountable. I don't know if this will make you feel less freakish, but I've gotten letters from virgins older than you. At least you're not toting that burden around with you.

This might be a shock to your system, but you're far from the only freak on the planet who thinks himself unworthy of love. Just about every time I've been dumped (and believe me, I've been dumped plenty!) or rejected (ditto!), I become utterly convinced that nobody else will ever love me and I'll spend the rest of my life utterly alone.

And whereas your self-loathing led you to retreat into booze and hookers, my pathology manifested itself by gravitating me towards abusive jackasses, because for a long time I fully believed I deserved nothing better. Sound familiar?

And so you slept with a couple hookers-big deal. Hiring a sex professional to comfort and fellate you is about a billion times more sensible than several other options you could've pursued.

That said, there's absolutely no reason in the world you should tell potential dates about your history! Noooo! Would you drop trou and exhibit your hemorrhoids at the dinner table, just so she knows your ass doesn't look nearly as cute naked as it does in those flattering 501s? Would you want to hear about her nipple-hair removal routine before the main course? I think not.

A huge, gigantic part of being a successful dater is knowing when to shut your big fat yap. I can't tell you how many men blow it on the first date by yammering on about "the one who got away," or-worse still-their "psycho bitch ex." Women who are attracted to you definitely do not want to hear about all those who've gone before them-whether those pioneers were supermodels or sex workers (or some combination of both). Your job is to make your date feel special; like she's the only person in the room. Dredging up ghosts of "paramours" past is the quickest way to queer the deal.

Once you've moved beyond casual dating and into relationship territory, you can decide how much-if anything-to tell her about the dark years. Up until that point, be vague. "I had a lot of problems," or "I don't like to talk about the past with someone I'm interested in having a future with," are two good evasive tactics.

You're 100 percent right in assuming that a lot of women would freak if they found out their men had ever paid for sex. I'm not saying that attitude is correct or makes any sense, but it is prevalent. So I would keep any revelations vague. You don't have any contagious "souvenirs" of your past, so it's not like you're under any moral obligation to spill. I'm not saying you have anything to be ashamed of, it just seems foolish and counterproductive to let your past taint what could be a very happy future.