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Get Naked: Sex advice for New Yorkers (September 13, 2012)

Jamie Bufalino advises a size queen to step down.

Photograph: Courtesy Shutterstock

Q I am a 37-year-old divorced father. I separated from my wife about one and a half years ago. About six months ago, I decided I was ready to start dating again. In June I met someone online and we immediately hit it off. We went on a few dates, and they were all pretty great except for the last one. Nothing sexual happened during the dating, but there was affection. On the last date I kept thinking, I’m going to kiss her and she is going to be receptive, but I was also incredibly apprehensive and completely wussed out. From there I became an emotional mess and revealed too much to her and became too clingy and that likely made her lose interest. Now this woman won’t even talk to me. Before I met my ex-wife, I was in a three-year relationship and I surprised myself by working up the guts to dump her, which is something I had never done before. Until then, I was always a “nice guy” who did everything he could to please women and made myself their bitch, which always led to relationships destined to fail. So I dump this girlfriend and something magical comes over me; I date around with a confidence I never felt before. Then several months later I met my ex-wife. This new confident me hit it off with her immediately—the old me never would have gotten anywhere with her. Yet I still was able to maintain my niceness. I feel like I have now lost that swagger. I can’t help but think that if I hadn’t become an overly sensitive wuss with this last woman, she wouldn’t have run away. So now I want to try dating again, but I don’t know how to get my mojo back. I’ve read books, visited websites, kept repeating positive affirmations to myself, but nothing seems to help. I want so badly to meet someone and be the best me I was five years ago, but I am completely lost on how to get back there. Please help.

A I think your goal should be to stop thinking about yourself in such a schizophrenic way—as either the self-assured, got-all-the-moves ladies’ man, or the weak, needy, hapless romantic. The fact is that every guy can feel like either of those types on any given day, depending on how much he lets the angels or demons inside of him control his worldview. I do find it a bit troubling that you see such a strong association between your self-esteem and the act of dumping a woman because you no longer want to be her “bitch.” There seems to be some misdirected anger at women happening there. After all, she didn’t make you her bitch, you made yourself her bitch (whatever that means, exactly). Which brings us to the next key lesson you should learn: Speak the fuck up while you’re in a relationship. Nobody wants to date a phony “nice guy;” they want to date a real guy who is nice but also expresses authentic emotions, including disappointment, anger (expressed appropriately), sadness, frustration, etc. Going forward, you need to learn to make peace with the fact that you have both strong and weak sides to your personality. You may have lost this latest woman because you overshared your anxieties, but it wasn’t the “sharing” that was wrong, it was the “over” part. When people see themselves in such stark, opposing ways, they tend to overindulge each aspect. Moderation is the key. Oh, and you may want to cut back on the use of the word mojo. I’m pretty sure that term went out of fashion long before you became single again.

Q I’m an attractive, tall, successful gay male in his thirties, but people think I’m in my twenties until they hear my life story. My issue is I go on a lot of dates, but I am only turned on if the guy is well-endowed. My dates don’t usually wind up in the bedroom (my choice), but I like to take things slow. However, I risk investing time and then coming out with the short end of the stick. Regardless of how great of a catch they are, if it’s average, there is no future. I try to be sensitive, but I’m tired of feeling like I should apologize or feel guilty because I like a big sausage. Should I be up front about my big dreams?

A First of all, how could you not include details about your life story? You can’t dangle a big, fat, potentially juicy tale in front of the “Get Naked” community and expect us not to be disappointed by the complete lack of anything to back it up. (Ha! See what I did there?) Secondly, are you kidding me? You really base your whole romantic life on the size of a dude’s pecker? That doesn’t seem like the most intelligent approach to finding a truly compatible long-term partner. That’s why I think that you’re actually not in the market for a relationship—you’re really just looking for sex, which is great, but let’s be honest about it. Of course you should be up front about what you’re looking for. Why waste anyone’s time by beating around the possibly gherkin-encompassing bush? In fact, I wonder how you even manage to keep yourself interested in some dude if you’re constantly wondering what he’s got going on down there. I’ll leave you with this: Thanks to porn and their association with excessive machismo, big dicks continue to mesmerize many people like yourself. But it is indeed possible to find an average-size (or even tiny) guy whom you connect with emotionally. Then you can simply use the human brain’s capacity for fantasy to compensate for whatever’s lacking in length and girth. There’s no reason to feel guilty about your sexual needs, but you should consider whether you’re actually shortchanging yourself with your predilection.

This seems like a perfect time to once again poll the “Get Naked” readership. Here’s the question: What’s your most memorable encounter with a ginormous cock? Or, if you’re a guy who possesses one, what’s been your experience with how sex partners or just casual observers have reacted to what you’re packing?

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.