Photo: Everett Collection

When I was in my mid-twenties I briefly dated a very successful, very unattractive guy I’ll call Movie Maker. I was at Void with friends, and as soon as he was introduced to me I felt woozy because I was such a fan of his oeuvre. It didn’t bother me that he was one of the uglier guys I had seen in my life. On the contrary—I decided that his low hotness was a great counterpoint to his high Q rating. It didn’t matter how successful and sought-after he was. If he was that weird-looking, he would never leave me.

So I hit on him. I must have done something right because a few hours later we found ourselves horizontal on his futon. He put on an OCMT (obsessively compiled mix tape), and we rolled around for a while before falling asleep. The next morning when I got home he left a sweet message, and I called back, over the moon. We went out two more times, and he revealed himself to be an incredibly narcissistic, gloomy guy who was totally preoccupied with his career. He finally dumped me because he didn’t have the emotional space for a relationship.A few weeks later, I ran into a girlfriend at a party. “Someone told me you’re dating Movie Maker,” she said.

I shook my head no. “I was,” I said, “but he turned out to be a self-involved jerk and broke up with me.”

“I dated him, too,” she said. “And he dumped me, too. He’s dated every artsy, cute Jewish girl in the city. We all make the same mistake. We go for him because of his name but think he’s some diamond in the rough because he’s ugly. Except it turns out he’s getting laid left and right because every girl’s thinking the same thing. He’s a bigger player than a good-looking guy.”

“You’ve hit on it!” I squealed, and we jumped up and down a few times, feeling like twin Jessica Fletchers.

I haven’t seen Movie Maker in five years, but recently I caught up with my girlfriend again. She’d moved to L.A., bought a house, and found a husband. “Why do we go for ugly guys?” I asked.

“When you date an ugly guy who’s smart and interesting,” she said, “you think you’re getting a good deal. You’re getting him on sale. You think an ugly guy will be more grateful and treat you better.”

But of course that’s not true. Cheaters come in all shapes and sizes, and some good-looking guys are so loyal that they’re faithful.

Some women fall for ugly guys in spite of themselves—they meet them, have a bland reaction, then come to know and love them. I’ve fallen for ugly guys for a much more obvious reason: They’re grateful, which makes for better sex. I once dated a guy so heavy he practically killed me every time he got on top, but he told me I was beautiful and he could never keep his hands off me, which I loved. My friend Stella, 31, a writer, can relate. “A guy who’s not as attractive as you is more likely to tell you that you are, especially in a place like New York, where so many women are skinnier, curvier, taller, and have clearer skin. I like to hear that. And a lot of guys I’ve dated never say it.”

Of course, in this city, a woman’s choice to date ugly may be more survivalist than anything else. In cities like L.A., every guy looks like a model, but most straight guys in New York just aren’t that gorgeous. So we don’t trust the handsome ones. “When I see a really attractive guy,” says Stella, “I assume he’s gay or a player and I don’t even bother talking to him. If something about him screams sexy, that’s never a good sign. Those are the ones you should run away from.”

Come to the Dark SideThree bars where nobody will care what you look like.