“I’ve never been in one of these relationships, exactly. But I’ve certainly been generous with previous girlfriends. And since joining the site, I’ve been on a few coffee dates. Pretty positive experiences, actually. I met an editor for a fashion periodical, a translator for the U.N., and a girl whose dad”—he stopped to laugh—“whose biological dad had just cut her off. The only negative experience I had was with a girl who was dating a hedge-funder. She said he had given her her nose and her Birkin bag, but that she needed cash. A bit mercenary for my taste.”

Over the course of two hours, Charlie and I discussed everything from the challenge of monetizing an Internet business to how laughable it is that one of the biggest distributors of pornography in the U.S. is the devoutly Mormon Marriott family (thanks to the in-room entertainment they offer at their ubiquitous hotels). We truly clicked.

That Friday, following a week of kind reminders from Charlie that he had enjoyed my company and found me to be pretty, we met for cocktails at a cozy bar in Tribeca. Again we had a lovely time, although I had to cut it short to attend a dinner at eight p.m.

When I stood to leave, Charlie stopped me. He turned suddenly serious. “Would you have sex with me?” he blurted out.

Almost without thinking, I said, “Of course!”

“Why?” he asked. A trickier question.

“Why not?,” I replied cheerily.

“Bad answer.”

Fuck, I thought—I didn’t want to lose Charlie. In an effort to ease the tension, I changed my tone and said, “Let’s see how it all unfolds.”