Get Naked: January 6-12, 2005

Q am a 34-year-old unmarried guy. I have slept with three women in my life. Whenever I tell people this they are shocked and they bombard me with questions. Are you religious? (No.) Do you masturbate? (Yes.) Do you enjoy sex? (Of course.) For reasons I don't understand and can't explain, I have always considered sex a Big Deal and have lived my life accordingly. I'm comfortable with my life choices, but I hate feeling defensive or dysfunctional whenever people talk about their "number." New York is supposed to be this bastion of the nonjudgmental, where you're free to be whoever you want without anyone caring. Anyway, my reason for writing is twofold. First, I hope you publish this because I think there are more people like me than the media would have you believe. Shy people get no ink. And second, how does a guy meet a nonreligious woman who also thinks sex is a Big Deal?

A Although I do believe that New York City is generally a place where you're free to be whoever you want to be without anyone (or at least most people) giving a rat's ass, the idea that it's also a bastion of the nonjudgmental is complete hogwash. Secretly judging others is one of our favorite pastimes (as opposed to publicly judging others, which we do everything in our power to avoid whenever a jury-duty slip makes its way into our mailbox). It's not something to be proud of, of course, but being judgmental kind of comes with the competitive, packed-in-like-sardines, melting pot–ish territory. How else are we supposed to cope with the multitude of lifestyles we see marching past our windows on a daily basis? We see someone opening the door to her Upper East Side townhouse and we immediately think, Sure, she's rich now, but how many old geezers did that walking bad-dye-job have to sleep with to get the keys to that palace? Or, as happened to me recently, you spot a transvestite prostitute ushering his/her john into the below-ground garbage-can area of a neighborhood brownstone and you think: I'm all for exotic gender-bending sex, but why in God's name would someone want to receive a blow job in a place where I don't even want to drop my recyclables? Judging is our go-to defense mechanism. It gives us a chance to take stock of our lives and think, Wait a second, am I truly happy or am I missing out on something by not having trannie trash-can sex? It's not clear to me whether you've had sex only three times or if you've had lots of sex with just three women, but either way, you suddenly became the "exotic other" among your group of friends. I wouldn't waste any time brooding over their finger-pointing or second-guessing your life choices, I'd just make sure that you're actually being honest with yourself about your own personal sexual agenda. Is sex truly a big deal to you, or is that just a cover story for the fact that being shy has prevented you from throwing it down as much as you'd really like to? And while you're at it, you might also want to work on keeping your own judgment in check. For instance, what makes you think most New York women (whether religious or not) don't consider sex a Big Deal? The truth is, if you just get up the gumption to put yourself out there more, I have no doubt that you'll find plenty of women who share your sexual point of view.

QI am having an issue with my boyfriend's penchant for making friends with other women. We have been together for three years, and in that time I have become familiar with his many women friends, many of whom are ex-girlfriends. This hasn't bothered me but I do feel threatened by the girls he has become friends with since we started to date. One in particular has me in knots. My boyfriend is a writer who received a seductive fan e-mail from this woman. He decided that it would be fine to write her back, which didn't bother me at the time because the whole thing seemed silly. He told her off the bat that he lives with his girlfriend. They ended up finding out that they have a lot in common and started to e-mail frequently. The e-mails then turned into phone calls, and now they have half-hour-long phone calls once or twice a month. He tells me I have nothing to be jealous about, that she has just become a friend with whom he can talk about art, literature, wine and The Simpsons. He tells me I have nothing to be jealous of because she's a thousand miles away, but I can't help my feelings. How can I get my point across without sounding jealous and accusatory?

A It's kind of hard not to sound jealous and accusatory when those seem to be the two main traits you've got going for you at the moment. Good God, woman, just let the man have his little chats about the chocolate undertones of an Australian shiraz or his favorite Krusty the Clown lines. She lives 1,000 miles away, for crying out loud. It's not like he can just sneak off for a quickie rendezvous—unless, of course, she flies here and they have an illicit hotel nooner while you're obliviously at work, or maybe she's discovered a way to telepathically transport her clitoris, which means he could be brain-fucking her while you're sitting right across the dinner table from him. In case you haven't figured it out, I'm trying to tough-love you into realizing that you're going to drive yourself (and your relationship) over the edge with this kind of maniacal jealousy. Trust me, the harder you try to keep this man glued to your hip, the faster he's going to try to unstick himself from such a suffocating situation. Take deep breaths, flex those trust muscles a time or two, and please, please, please, just give him a smidgen of space.

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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