QI just turned 30. I think I’m pretty hot, have a great body, possess smarts, a good job and ambition. Most people when they meet me think I’m 26 or thereabouts. To be honest I don’t really give a fuck about age, mine or anyone else’s, except that, as soon as I tell guys how old I am, they run for the hills. I was dating a 24-year-old earlier this year and we went on a couple of pretty amazing dates, and I never saw him again after I told him my age. It’s been two years since my last “real” relationship. My ex-boyfriend broke up with me and then got engaged within two months to my archenemy; it completely broke my heart, and it’s taken a lot of hard work to get me back in a place where I feel okay to even start dating again. So this ageist attitude in NYC is not doing wonders for my self-esteem. I’ve never thought of myself as someone who would lie about her age, because I believe in self-acceptance, but I’m beginning to have faltering faith in the straight boys of New York and their ability to retain open minds. Please tell me I’m wrong, or else that it’s okay to start saying I was born in the ’80s!

AWow, you have an archenemy? That’s cool. It sucks that she got your man, but perhaps you can get her back by poisoning the city’s water supply with laughing gas. As for your age situation, I’m sorry, but I’m just not buying that it’s simply being 30 that’s putting the kibosh on all of these relationships. You may have circumstantial evidence to back up that claim, but I’ve got one hard-and-true fact for you to face: A 24-year-old guy doesn’t even need a real excuse to break up with someone. You see, he’s hardwired to go out and get as much pussy—aged or otherwise—as possible. So if you still want to play in the kiddie pool, you’re going to have to be prepared for a life of serial dating until you find one who’s ready to settle down early. And since I have trouble believing that 30 is such an off-putting age, I refuse to give you my permission to start lying about it. I once knew a woman who was so freaked out that her new, younger girlfriend would dump her because of her age, she shaved a whole decade off. Naturally, the truth came out (because how can you really keep that a secret for an entire relationship?) and it turned out to be no big deal, although they did eventually break up for a host of other reasons. The moral here: Have enough faith in your desirability as a girlfriend to not start a relationship off with a lie. You may be going through an unlucky streak, but let me assure you that there is no shortage of hot guys—of every age range—who would prefer a self-assured 30-year-old over an insecure faux-28-year-old.

QI’m a 40-year-old gay guy and I finally met a man that I think has real potential. He’s sweet, very cute, well built, reliable, levelheaded, gainfully employed, and we get along well. So of course I’ve been waiting for the other shoe to drop. I think it just hit me in the head. At first, I thought he was a bad kisser, but eight weeks in, I’m coming to another conclusion, one of two possibilities: (1) He just doesn’t like to kiss. (2) He just doesn’t like to kiss me. I think I’m going to have to break down and do the unthinkable and talk to him about it. I don’t think it’s my hygiene (at least, I’ve never received those complaints before, and I am diligent about such things). But this kissless sex is for me much like opera performed by mimes, pie sans la mode, Beavis & Butt-head without fire—you get the idea. I think I’ve arrived at the deal breaker. Advice?

AIt’s not often I get a letter from a guy who references both opera and Beavis & Butt-head, so I feel particularly sorry that someone as well-rounded as you has been aggrieved by smoochless sex. Of course, I’m not sure why you think it would be unthinkable to broach the subject—awkward yes, but what other solution is there? A conversation like this requires a certain amount of tact, so if I were you I’d begin by saying something like, “I’ve noticed you’re not that into kissing, and I was just wondering if my breath is the problem or…” (leave a nice long gap after that or, to give him lots of time to fill in the blank). Who knows, maybe it is your breath, which, although embarrassing, would actually be the best response, because that’s something you can rectify. If that’s not the answer, I’m not so sure his being averse to kissing has to be a complete deal breaker. In the most successful relationships, each individual brings out the best in the other. How great would it be for you to introduce this guy to the world of sloppy sex kissing? Don’t write it off so quickly, and definitely keep me apprised of the results.

QMost of us know quite well where we fall on the “looks” hierarchy. I, however, have absolutely no idea where I fit in. With so much of gay culture revolving around what is considered “beautiful,” one would think I should know by now. I will go to a bar one night and no one will even look at me (or they’ll do the time-honored “look then look away” with an expression of disgust). The next weekend, I’ll go to another bar and suddenly men are all over me. New York City men, in general, don’t find me that attractive, but they love me in Chicago and Philly. I’ve been told everything from “You’re ugly” to “You’re the handsomest man I’ve ever seen.” The question, “How attractive am I really?” still gnaws at me. Is eliciting such extreme reactions to one’s looks normal? Am I a model or a sideshow freak?

AI think your first mistake was trying to get into a valid discourse on aesthetic beauty at a bar. Your second mistake was not providing a photo along with your question (although to be honest, I probably would have given you some wishy-washy answer that focused on all your best physical traits and ignored the lesser ones). Look, you’re not the first person to find out that New Yorkers are a tough audience. The good news, however, is that New Yorkers also tend to admire quirkiness more than people in other places, so even if you have some weird face issue going on, there are still plenty of people out there who will find you hot. I’ve got an idea: If you really want to get at the truth, you could send me your photo and I’ll put it up at timeoutnewyork.com and we can have readers judge you. To be honest, if I were you, I’d never do that, but it would be really fun (for all of us) if you did, and a true test of self-esteem for you. In fact, while we’re at it, why don’t we open up this torture-fest to all “Get Naked” readers. Just send your photo to sex@timeoutny.com and once we get a bunch of them we’ll start up TONY’s own version of Hot or Not. Of course, when you’re doing the judging we’re going to want some input on what exactly makes the person hot or not. So be honest—but not brutally honest, if that’s possible. Thanks.

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.