Get naked

Q I’m a 32-year-old gay man. About six months ago, I became friends with a nice guy, but we’re just friends. I felt no sexual attraction to him. I recently heard from a “credible source” that my friend is massively well-hung. Now I feel awkward around him because I would love to know what he’s like in bed. It’s kind of like being back in high school, when I wanted to see the hot guys in the gym shower. The last time we hung out, my friend noticed I was uncomfortable. I tried to play it off by saying I had a stressful week at work. What should I do about this situation?

A Before I give you my advice, I should tell you that I’m one of those people who sometimes doesn’t have a filter. For instance, the other day I was at a fund-raising dinner for Tibet and one of my tablemates asked me for my thoughts on the Dalai Lama. My response: “I think he’s a great guy, but I can’t get past the accent.” That happens to be my honest, juvenile thought—the unvarnished truth—but what kind of jackass says something like that at a Tibet dinner? But the funny thing is, it turned out to be a total ice-breaker. The guy who asked me the question admitted that his initial reaction to the Dalai Lama was similar (“Whenever I heard him speak, he sounded like a child to me,” he said), but when he really listened to the holy man, he was touched by the power of his message.

This is a long way of saying that I think you should come right out and broach the subject of this dude’s big dick (we’re not still talking about the Dalai Lama here, just to be clear) with the guy himself. But don’t do it in an “I want to have sex with you” way, do it in the potentially less off-putting “I would love to eyeball that freak of nature between your legs” way. Although the thought of this guy’s big dick has sexualized him more to you, I think your initial determination about the lack of attraction is the more authentic response. So let’s keep this strictly at the voyeur level, and make sure you keep the discussion about him showing off his goods light-hearted, not creepy. Of course, the risk is that you end up making things even more awkward, but given the current uncomfortable situation, that doesn’t seem like such a big gamble.

Q I’m a male in my mid-twenties. I’ve had nerdy interests and behaviors my whole life. As a result, I don’t get laid. I have had sex with three people in my life, and have never had a girlfriend. I get phone numbers frequently, but almost always get rejected quickly. I am doing everything I can to be more attractive. I’m physically active and am trying to upgrade my wardrobe. I’ve been seeing a therapist. But, in the meantime, I’m trying to identify any repulsive behavior I have, and address it. At this rate, I feel like I’ll have my first girlfriend at 35. How can I speed up this process?

A This is probably going to blow your mind, but it’s not being nerdy that’s preventing you from getting laid. It’s that you’ve internalized all the negative messages that the dating process transmits. The idea that you think there’s something “repulsive” about you is heartbreaking. People bail out of relationships for all sorts of reasons—and most of them have nothing to do with the person they’re leaving behind. Yes, being fit and well-dressed can help draw women in, but that’s not going to seal the deal. You need to use that therapist to help boost your self-esteem, and start entering relationships with the idea that a woman is damned lucky to land a guy like you rather than expecting the sad-sack past to repeat itself. If you can do that (or at least fake it until you can), you’ll have much more success.

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.