My obsession with brainy men probably began in 1999, when I moved to Manhattan with dreams of (zippety-do-da!) becoming a novelist. But sometimes it seemed I was more dedicated to honing the art of picking up writers and other intellectuals … in the city where the brightest of them lived.

I was finally driven to swear off the type by one mental masturbator in particular—a young philosophy professor who was working on a novel himself. Smart and sexy, Phil constantly used surname adjectives: He was always describing things as Marxian, Kantian, Jungian. Being with him made me feel both Sontagian and Monroevian, until the day he announced he didn’t “believe” in fidelity. (I thought: You don’t “believe” in it. You just do it.) It was unrealistic and self-defeating, Phil said, to expect a single person to be your ultimate sexual, psychological and intellectual match. Suddenly, I felt dumb and ugly. Bridget Jonesian. I bowed out.

But I wondered: Why do I always end up with his kind? Why am I always drawn back to men who prefer a world of the mind to the real one? Do I hope their brilliance will rub off on me? Am I hooked on that nervy feeling of always waiting for the next intellectual lob? Is it because my father is a construction-working Irish immigrant who barely finished grade school, so I’ve always felt like a literary-world impostor, and I think these jokers can legitimize me?

I hadn’t come up with a satisfying answer by the time I went to Martha’s Vineyard for a July weekend, where, one night at a bar, I met a handsome Irish landscaper named Mike. We flirted near the pool table. Feeling slightly Pinoted, I squeezed his biceps.

You’re objectifying him! I heard Phil say in my head. Besides, can’t you see it’s Freudian?

A few minutes later, Mike held my hand as we walked down the moonlit cobblestone street. We went back to his place and made out a little (PG-13 style). When I ferried away the next morning, I was sure I’d never see him again.

Except that Sunday night, Mike called … just to chat. And did it again the following night. A few easy and pleasant conversations later, Mike suggested visiting me in the city for the weekend.

I balked. We barely knew each other! Besides, when I decided to aim for “anti-intellectuals,” I was thinking more about hedge-fund managers, movie execs, maybe even dentists: men who were educated—just not overeducated to the point that it infected every thought. Men who could simply make it through a meal without worrying about the Foucaultian implications of their relationships to the waiter.

But hold on a second, I told myself. Isn’t Mike exactly the kind of person you’ve been wanting? Someone who leads with his heart, not his head? Someone interested in making plans for the future? (Phil had trouble agreeing to dinner a day in advance.) Someone more interested in you than in philosophical B.S.? The anti-Phil?

So, that Friday, Mike arrived. After setting ourselves up in the posh apartment a friend had loaned me for the occasion, we headed to Wallsé in the West Village for dinner; drank too much wine; bopped over to Turks & Frogs; went home. It all felt exactly right: like the start of a romantic weekend with a guy who was clearly committed to me.

But by the next afternoon, in the bright and slightly hung-over light of day, my attraction to him did a quick fade. Mike and I had already told each other our lives’ stories, and, as we walked lazily around Central Park, I found I had nothing to say. Worse, I wasn’t the slightest bit interested in hearing from him. I actually tried to send him to the American Museum of Natural History by himself so I could have some downtime, but he was—understandably—slightly offended by my suggestion. So I agreed to go with him to a bar.

After a few, he started ranting about his parents’ divorce. Though it had happened more than 10 years earlier, the emotional wounds seemed uncomfortably fresh. “Why’d my dad do it?” Mike kept saying, rhetorically. “Why?” I wondered if there was something passive-aggressive going on: Was he expressing his anger with me indirectly by talking about how furious he was with his father?

I thought about how Phil knew exactly why his father had divorced his mother: because she was more successful than he was, and his father felt emasculated. With Phil, there had always been a tidy answer, an interesting way of talking about it. But Mike’s messy meltdown was making me feel seriously nervous. Something in me turned off completely. I’m sure he wasn’t surprised when I slept on the couch that night.

By morning, we both seemed to know the spark was gone, but to have silently agreed, nevertheless, to make our last 24 hours as polite as possible. When I suggested multiplex-hopping—in other words, being together without talking—he agreed enthusiastically.

After two big-screen movies, we stopped by the apartment to shower and change, but when we headed out for a third flick, Mike couldn’t open the apartment door. “That’s funny,” he said. “Seems to be stuck.”

We called the super, who tried opening the door from the outside: No dice. Mike attempted to jimmy the thing using a knife, while I thought, I can’t believe I’m trapped in here with him! Though at least Mike was trying to do something. Phil would have paced around quoting passages from No Exit and muttering about absurdity. Then he’d demand sex (which didn’t sound so bad at that point).

Finally, I ordered a locksmith. Not only had the weekend totally sucked, but it looked like it was going to cost me two or three hundred bucks.

I’d just hung up when Mike shouted, “I did it!”

I high-fived him giddily. We skipped the movie in favor of celebratory drinks and burgers, and Mike grabbed the check—as he’d been doing all weekend.

He’s a good guy, I thought. And you’ve been a real jerk.

Sexual tension didn’t suddenly reappear, but a camaraderie emerged: Mike told me about his ex-girlfriend, and I talked about Phil, as well as the hordes of others like him I’d been involved with.

“Why d’you date so many wankers?” Mike asked.

“Great question,” I said. “I’ve been trying to figure out the answer all summer.”

But it wasn’t till the next night, when I was delighted to be home alone—to be back to writing my novel, to be making a snow angel in my huge, clean white bed that I didn’t have to share!—that I started to wonder if maybe I was the wanker. The commitment-phobe.

Did I like writer types because they, like me, only really care about one person: their inner scribe? Did I fall for Ph.D.’s because they kept an intellectualized distance from their experiences, so that, while dating one of them, I’d never have to witness anything as psychologically unpleasant (for me) as Mike’s meltdown? Maybe that’s why I became a fiction writer in the first place. Rather than getting emotionally involved with real human beings—unpredictable, frightening, capable of betraying me—I only get wrapped up in my characters, who will never do anything I don’t make them do.

How fascinating! Needing to discuss it further, I called … Phil.