Just one of the girls

Could I be friends with a woman I sort of wanted to see naked?

That was the question I found myself revisiting six years after I officially swore off attractive female friends. In 10th grade, I fell in love with Emmy Abrahams and spent the entire year in English class in a Shakespeare-induced obsession.

That started an unhealthy pattern: Matt meets girl he thinks is cute. Matt endears himself to said girl by talking to her about the boy she likes. Girl, therefore, sees Matt as a friend-girlfriend-sister-mother, rather than a boyfriend-lover-booty call.

I repeated the pattern every year. The friendships would involve long phone calls where we’d talk about other guys. For hours.

I would dispense advice like I was one of the girls. For hours.

I would then lie in bed alone feeling miserable. For hours.

So junior year in college, I called it quits. No more female friends. Only the following women would be exempt from the new rule: Current female friends, ex-girlfriends, women in different cities and my friends’ spouses, fiancees and sexual partners.

I also began subscribing to the ladder theory. LadderTheory.com explains that when men meet women, they put them on a ladder of desirability. The more attractive the woman is, the higher she goes on the ladder.

Women do the same thing when they meet men. But they actually have a second ladder for friendship. Men, therefore, are immediately designated to either the “friend” or “boyfriend” ladder. Worse, according to the theory, you can’t switch ladders. Once you’re on the friend ladder, there will be no possibility of physical contact. Ever.

For years, the ladder theory seemed to hold true, so I stayed away from female friendships. I didn’t have to have all-night conversations with women about the cute boys at school ever again!

Then, I met Deb.

Deb told me that, yes, men and women can be friends.

I didn’t buy it. I knew exactly what was going to happen: In the beginning of our friendship, I would repress the fact I sort of wanted to see her naked. Then, after I started giving her advice about guys like a good little girlfriend, I would realize that, yes, actually I do sort of want to see her naked.

Then, I would be miserable.

I explained this to Deb (well, not all the naked parts) and then we continued the discussion over e-mail.

“Listen, if our friendship isn’t enjoyable and doesn’t benefit you because we won’t have sex, then that’s fine. We don’t need to hang out,” Deb wrote. “I will be disappointed because I really enjoy my time and conversations I have with you.”

Sure, I felt a bit rejected. But you have to admire the honesty. She told me straight up how it was and then she offered me a deal.

“Let’s do something completely original,” she said. “Boy and girl are friends in the same city with no sex or past sex or future sex.”

I thought the term “past sex” seemed a little harsh. But still, regardless of what she looked like, I really did enjoy spending time with her. So I agreed to the offer.

As I write this, it is day four of the friend arrangement. So far, so good. I haven’t been jealous when she talks about other men. I didn’t cry myself to sleep when we returned to our separate apartments after a night out. And I even considered setting her up with one of my friends.

But I still check her out when she walks in front of me. I also have had at least one dream about making out with her in some strange, long hallway.

And that’s why I remain skeptical about the arrangement. I mean, I don’t check out my friend Dave when he walks in front of me. And I certainly don’t have dreams about kissing him.

Could this actually work?