Since I figured "it" out, during the summer after my senior year in high school, I've gone out on dates with about 130 guys (a "date" is defined as a social event followed by bedroom activity).
Maybe 10% were spectacular, the stuff of memories and blog posts.
80% were pleasant, just everyday life in a gay neighborhood.
But 10% were Dates from Hell. Sometimes the social event went wrong. Sometimes the bedroom activity was miserable. But most often the guy turned out to be mess.
Here are some dates that I would like to forget.
College
Jack Kerouac and his Bratwurst. I spent two weeks hanging out in the Student Union with Jack Kerouac, aka Jurgen, a hipster writer who smoked a pipe and wrote horrible poetry. I finally got the nerve to ask him out, to a meeting of the Quad Cities Writers Club. When I got to his house, I was greeted by his live-in girlfriend! But I did get a sausage sighting.
I was visiting Des Moines for my first gay rights march, when I asked a cute guy wearing a mesh t-shirt for a date. He agreed. At the end of the date he said "Follow me home." He drove like a maniac, zooming around corners, running stop lights. Finally I lost him.
West Hollywood
The Kept Boy who Alan and I picked up at Mugi. He had a fantastic physique, but neither of us realized that he was drunk. And getting drunker by the minute.
Mario in the White Room. A neat freak with a pristine white-draped apartment like a hospital room, who made me put my clothes in the washer before we could climb into bed. Where he called me "honey" and was not into kissing (too many germs).
In Nashville, I accepted a date with a closeted country boy, a student at Vanderbilt, with an infinite number of rules and quirks. After a truly miserable date, he ended up giving me the wrong number. I got revenge by looking him up in the student directory and calling him anyway.
The Worst Date in West Hollywood History. Ok, Ryan the Dwarf was nice, and very cute, but everything went wrong: a rainstorm when we wanted to go sailing, turned ankle when we wanted to go dancing, missing the concert, Ryan getting drunk, losing Lane (who was supposed to join us).
The Bear with the Pierced Penis. The pierced penis wasn't the worst thing about the date. Or the swimming pool on a chilly winter night. Or the pot. Or the poppers.
New York
The Most Embarrassing Guy in the World. Jesse the 17 year old college freshman, who ordered a hamburger platter in an Indian restaurant, wore short pants and shoes with no socks to a grad student party, and said the most insulting thing I've ever heard during oral sex.
The Nastiest Guy in the World. Terrorized an online chatroom with his constant abrasive, abusive comments. I agreed to the date only because I was desperate to move into Manhattan, and he had a room to rent. Actually, he didn't. He lied in order to get me to go out with him.
Mario the Teen Model. I was 39, and he was 19. And I learned a valuable lesson: make sure you're back home, kissing on the couch, by 10:00 pm. Otherwise you may end up eating macaroni and cheese in a diner at 4:00 am.
Florida
Breaking Every Rule of Gay Cruising. This one was my fault: I didn't screen the guy well enough in advance. So I ended up in a half-built house in the swamp, cruised by two crazy roommates and invited to use drugs.
The Coffee Drinker. Drank coffee instead of beer at the Filling Station every day. I tried to say hello, and he said "I'm not into a relationship." Then Yuri landed a date with him, and invited me to share!
Ohio
Remy the Jerk. I was cold, hungry, insulted, and abandoned. It almost didn't make it worth Remy's Kielbasa.
The Huber Heights Horror. This one was his fault. He completely misrepresented himself and his intentions. I drove 20 miles in the middle of the night for a "date." and ended up with a hookup.
Upstate
The Grabby Male Nurse, one of the Gang of Twelve, gay guys who had known each other for years and had all dated each other. This one kept leering and groping, and made every word I said into a sexual double-entendre.
My Friend with Benefits. My boyfriend Troy was ok with "sharing," but when I started seeing another guy regularly, something had to give.
The Transman and His Angry Inch. Ok, so I read his online profile wrong. Not his fault. Still, what I found down there was rather surprising. And embarrassing.
Plains
Ricky with a Y, from last November, spent the entire date psychoanalyzing me. Even in the bedroom. "Is your aversion to anal sex a sign of internalized homophobia? Do you believe that if you don't go 'all the way,' you're not really gay?"
Brett, the Hookup from Hell, who lied about his age twice, suggested a bisexual three way, and then decided that he was going to start a new career as a hustler.
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