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5 Guys I’m Glad I Dated…


Each was a challenge, says one gay man, but here’s what he learned by going out with these unconventional types.

By Lee Bailey

f you watch too much cable television, you know that popular media believes in only one kind of gay guy: fit, fabulous, and fashionable. He loves to shop (and to tell other people how to shop), and he consumes hair products at a higher rate than a Texas cheerleader.

Personally, I’ve never fallen for the hairless, muscle-bound Adonis with blond tips—or the overeager shopping buddy. Looking back on my dating life, I realize
“Every gay man should know how to be a little straight, I think… ”
that most of the men I’ve gone out with have deviated from physical, social, and professional stereotypes of “good gays,” at least as mandated by VH1 and Bravo. But even though many of the men I’ve known weren’t picture-perfect homosexuals, I’ve learned a lot from them collectively. Here, then, are five surprising types of guys I’ve dated.

#1: The Guy’s Guy
“What? He’s gay? I had no idea.” I can’t begin to count the number of times I heard this said about one ex-boyfriend. Female friends of his would always make a point of telling me just how straight he seemed, and how they themselves had endured crushes on him. He had nary a gay friend, and passed his evenings with straight pals at the local dive bar, playing pool and watching football. Though I myself tend toward these pursuits (hence our original attraction), he took it to an entirely different level, enthusiastically commenting on women’s curves and behaving in a super-competitive fashion. I believe that most of these behaviors were part of his natural personality, but I have no doubt that some of them were affected as part of some self-denying instinct he harbored. He was older than me, and I think that as a child of the late ’70s, he wasn’t entirely comfortable with what being gay really involved.

Why I’m glad I dated him: Being able to talk about gridiron, admire she-booty, and evaluate lagers are all valuable skills, and I must admit that I learned many of them from the Guy’s Guy. Even though I live in New York, which I like to think of as the gayest city on earth, most of my friends aren’t gay, and I relate to them in many ways I that picked up from this fellow. As Weezer sang, “Everyone’s a little queer, why can’t she be a little straight?” Every gay should know how to be a little straight, I think… just to relate that much better to the rest of the population. Go ahead and disagree, but it worked for me.

#2: The Obsessive-Compulsive
“Wash your hands!”
“Why?”
“You pressed the elevator button!”
“But I pressed it with my knuckle!”
It was after this exchange with one former boyfriend that I realized I was dealing with something serious—something clinical. Slowly, other obsessive-compulsive behaviors surfaced, and when I asked him about them, he admitted to the diagnosis. He couldn’t go to bed unless every dish was clean—not just dripping in the dish rack, but actually dry and put away. Same for clothes. No sock was to be left on the bedroom floor. He was like Faye Dunaway in Mommy Dearest, but in real life.

Why I’m glad I’m dated him: Hello? Cleaning lady and boyfriend all in one? What’s not to like? But seriously, being with someone who is that consumed by order and exactitude serves as a helpful reminder to the rest of us that sometimes you just have to let things go. It helped me see that, frankly, I never wanted to let myself get that possessed by neatness.

#3: The Closet Case
Remember in Scarecrow and Mrs. King how Kate Jackson had trouble keeping her life of espionage secret from all those who thought she was a mere
“Dating a compulsive socializer got me out of my hermit habits.”
housewife? Well, multiply that level of subterfuge by 10 and you have some idea of what it is like to date a guy who hasn’t come out. Of course, I didn’t set out to date a closet case, but it happened, thanks to a confession of interest he made one night after a few drinks. He was a friend of a friend, and everything about him was perfect—except for his seeming inability to come out. A strapping, all-American lad, he was irresistible. The relationship was clearly doomed, but I couldn’t stop myself from starting it.

Why I’m glad I’m dated him: Despite all the predictable angst his situation caused us, dating the Closet Case reminded me of the importance of putting myself in someone else’s shoes—in this case, white bucks from Brooks Brothers. He was from a very well-known, ultra-WASPy family, and it was this lineage that was the primary reason for his reluctance to reveal all about himself. He will eventually one day realize that honesty is the provenance of happiness, but I recognize now how much more of a challenge coming out is for some than others. I feel I gained some significant empathy from this guy.

#4: The Corporate Climber
I once dated a very successful advertising executive who always put work first. There is no faster way to make the guy you’re dating feel like an insignificant other than to place him toward the bottom of your to-do list, as this guy did with me. Worse, when we did spend time together, the number-one topic of conversation was generally his job. Should he switch firms? Should he confront his boss? Should he demand more in the latest of his many promotions? He didn’t want a boyfriend—he needed a career counselor.

Why I’m glad I’m dated him: While the “A” in Type A can stand for annoying and ambitious, it can also reflect admiration. Yes, his obsession with his job was tiresome, but it also led me to think more about my own career at the time. Was I missing what I needed and wanted out of work? Was I putting up with too much grief at the office? I decided I was, so I quit—shortly after breaking up with the boyfriend, thereby solving two problems at once.

#5: The Social Butterfly
Do you ever see technical specifications for cell phones along the lines of “holds up to 500 numbers in speed dial?” When I used to see these, I always wondered who on earth needed such an extensive directory in the palm of his hand. Then I met the Social Butterfly. Dating this man was like living in the Butterball Call Center the week before Thanksgiving. The phone rang non-stop, and meals, funerals, and sex were not considered sufficiently important to let a call go unanswered. And when I wasn’t with him, reaching him was impossible—he was always on the other line. No party invitation was declined, and no event was left without at least 30 double kisses bestowed.

Why I’m glad I’m dated him: Left to my own devices, I can be a bit of a hermit. Give me a good book and a duvet, and I could spend days in my apartment alone. Dating a compulsive socializer showed me that the yield of interesting people in your life is greater when you go out like a madman. I’ve since settled on a happy medium between solitude and Paris Hilton-level night-crawling, and am quite happy with the results. But I wouldn’t have gotten there without dating the Social Butterfly, so to him — as to the others mentioned here — I say thank you!


Lee Bailey is a New York-based freelance writer who has contributed to The New York Times and WWD, among other publications.
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