Q I am a 37-year-old heterosexual woman. I no longer have sex that much. This started nearly ten years ago. (Yes, there is a traumatic event there, and I did therapy and I feel good about myself, though I still have this lingering “men are shit” feeling.) I have sex every one to two years now. I fell for a nice guy recently, but he didn’t want anything real. So the last time I had sex, director Robert Altman was still alive (love him). I’m not itching to have sex. I masturbate rarely now. It used to be a lot. I used to cry at first about the sex. None of that anymore. I’m beginning to view sexual hunger as a weakness in others, and I’m happy to be clearheaded and to live my life and work really hard at my job without the impediments and confusion of those in relationships. There are highly accomplished people who have led virtually celibate lives. Yes, when I was kissing that nice guy I was hoping things would work out happily ever after, but when do they work out that way for most of us? Rarely. So many marriages are about going through the motions, loyalty, fear of dying or growing old alone, status, money, the need to avoid dating (that last reason is a good one). So given the low success rate, I’m actually just saving a lot of time that would be wasted. Is this sexually unhealthy? I hear a lot of people just give up, especially in the rat hole of frustration that is NYC, where there are so many people living anonymously that no one cares if you are unmarried.

A As someone who’s not exactly genetically and chemically predisposed to being happy, I instantly recognized your letter as the “Aw, fuck it!” cry of someone who’s given herself over to the gloom and doom of depression. Believe me, I’ve been there. Some people are born (or more accurately, raised) with the capacity to breeze through life without letting its slings and arrows pierce their sense of hopefulness and optimism. And then there are those of us who—for whatever reasons—feel the weight of the world’s slights and injustices to an absurd degree, and inevitably get caught in a phase where it just doesn’t seem worth it to fight to be happy. If I had the answer for how to once and for all conquer that sense of hopelessness, I wouldn’t still go through it myself (which I do). What I do know, however, is that it does no good to just give up and take yourself out of the fight. In fact, it only deepens the depression, because now you have no one but yourself to get angry at for not achieving the goals you deeply desire. Remember, depression is really just a consequence of unexpressed anger. Clearly, you haven’t gotten over that traumatic event, and you have to learn to get in touch with the anger you feel surrounding it, because that “men are shit” attitude is ultimately what’s holding you back from truly connecting with someone. Now don’t get me wrong, other human beings can truly be shitty (just wait till you read the letter after this one) and life can often be frustratingly unfair, but the key is to develop such a sturdy sense of self-love that no amount of ego-bruising could possibly topple it. Yes, that’s easier said than done, but as far as worthwhile pursuits go, they don’t come much more grand and noble than that one. I agree that it’s entirely possible to live a happy (perhaps even happier) life being single than married, but it’s clear to me that that’s not what you want. And since singledom is a perfectly viable option, why not get back into the dating pool without clinging to any preconceived notions or specific goals? Do it because it’s better than giving up, and because you see yourself as worth fighting for. Oh yeah, and because sex feels good.

Q Some advice would be appreciated here. I am a 24-year-old male. Last year I tried like hell to seduce this thirtysomething coworker who was married. She had already had an affair and was unhappy with her husband for a variety of reasons. The thing is, I only want to fuck this woman’s brains out. I tried every trick in the book, being a nerdy schmo, being the “on the verge of suicide” young brokenhearted collegiate. Hell, I even wrote her reams of letters professing my love (not!). See, I’ve been getting more than my fair share, and am bisexual as well. The workplace was an easy way for me to get my kicks. But I’m obsessed with getting this damn fool chick into bed. I haven’t talked to her in a few months; better to let the time pass, but I plan on coming on again strong with her…telling her I love her and only I can give her what she wants. And then, just like all the others, I will drop her silly ass after I fucked her…which is all I really wanted to do in the first place. Some New York women think they are so smart. Stupid fool may even leave her husband, and then where will she be? So why am I writing to you? Should I go ahead with my plan or should I give up and concentrate on where my current juice flows most? I’ve been screwing my fiftysomething former boss for months now and no one ever realized. I’ve just been racked with the feeling that there is unfinished business to be done. What say you?

A I say you’re a psychopath. The idea of wasting so much energy trying to get someone to fuck you, just so you can show them how completely disposable you think they are, is the sign of a truly sick individual. I hope this is just an act and that you’re just trying to get some jollies by creating a disturbed character for me and the “Get Naked” community, but if not, then I plead with you to get some help ASAP. You clearly have an empathy deficit, so if you’re even the slightest bit interested in resembling more of a human being, I would recommend doing something—like volunteering at a hospice or paying a visit to a nursing home—that will help you feel more for other people’s pain and suffering. I’m under no illusion that you would ever rise to such a challenge, but I just wanted to throw it out there just to remind you that life can be hard for people even when they don’t have someone carefully plotting to fuck them up.

Q I’m a 19-year-old college female and I’ve just started becoming sexually active. I haven’t actually had sex yet, but have done everything else. The guy I’m dating has a really unusual-looking penis. It’s superskinny, but it’s got a big fat head on it. I don’t have a lot of experience with this stuff, but I have seen plenty of pictures of penises before and none of them looked like this. Is he normal?

A Normal, yes. Aesthetically ideal, probably not. But if that’s your only complaint with it, consider yourself lucky.

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. Check out “Sex on the Street” with Jamie Bufalino at timeoutnewyork.tv.

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