The Romantic Résumé: In Big, Small Town, Everybody Knows

One summer, I was going through my cell contacts, trying to background-check this adorable doe-eyed L.A. wannabe screenwriter—call him Charlie Hollywood—I’d met in Chelsea. We had a weeklong fling while he was in town that ended with him inviting me for another tryst on his home turf. It sounded tempting: Neither one of us was looking for a long-distance relationship, but a week of commitment-free love in the city that’s never deep? Sure. Why not?

But before I agreed to do it, I needed one key bit of information. Or rather, non-information. I wanted to confirm that no one I knew knew Charlie—so I could make sure the whole thing stayed on the down-low. Not that there was anything wrong with Chuck. And not that I personally thought there was anything morally offensive about a little assignation with a single guy. But I worried what other people might think, and I’d been in New York long enough by then to know how fast word got around.

Every person in the city—myself included—has an unofficial rap sheet that is maintained and updated by the old-fashioned word-of-mouth method. (Sites like Friendster and MySpace have only made the system more efficient.) Therefore, my secret encounter with Charlie could very well become public knowledge if he was in any way linked to my network—which he probably was, since everybody seems to know everybody in the circles I run in: This person’s worked with that one; what’s-her-name grew up with who’s-his-face; so-and-so went to school with such-and-such.

Take the party where I met Charlie: There must’ve been at least three or four hundred people on two floors at this thing, which was thrown by a group of 10 and held at a warehouse-esque film-production studio. Yet, despite the size, I actually thought I wouldn’t know anyone there, because none of the hosts were in publishing and all of them were seven or eight years older than I was. Plus, the guy who’d invited me was someone I knew only tangentially.

But during the course of the night, men I’d been in some way or other entangled with swam around me. There was the biologist friend-of-a-friend whom I’d blown off. (He suddenly seemed so much cuter with that hot Lebanese girlfriend in tow). There was the venture-capitalist buddy-of-an-ex whom I’d gone out with a few times, before it ended ugly. There was the magazine writer I’d met on a blind date; we tried it for a couple months, till things mutually fizzled out. Not to mention the newspaper guy I’d picked up one night at the Ear Inn on a dare, only to realize the next morning that he worked with my boss’ husband. And then I saw the freelance hack ….

Well, you get the point. But as if to drive it home, suddenly the crowd parted and a brown Afro appeared: It was Malcolm Gladwell—the New Yorker writer who wrote about the six-degrees-of-separation phenomenon—appearing like Moses to remind me of the law of urban incestuousness.

That party wasn’t unusual. And the more I realized how small my dating network was, the more I worried about my romantic résumé: the hypothetical document I was convinced would make or break me for some potential boyfriend. “Well, well,” I could imagine some scrutinizing suitor saying. “You’ve made it this far—I know you have an impressive, um, skill set. But I’m worried about your hands-on experience. You did a lot of jumping from one thing to the next. A lot of—how can I say this politely—messing around?” I’d feel the sweat forming under my pits. “Let me explain!” I’d beg, but he’d put up a hand and continue. “I also see that, on a number of occasions, you’ve drunkenly gone home with people you then failed to have any—how can I put this—follow-up with. What do you have to say for yourself?” Silence.

My batting average when it came to healthy, well-adjusted adult romances was just about zero, and trying to pretend otherwise was sure to backfire.

Of course, mine was not the only invisible laundry list of conquests, breakups and indiscretions floating around out there. In fact, maybe the thing that convinced me it was time to give up my single-girl-in-the-city high jinks (or at least try to hide them better) was an incident involving that freelance hack I mentioned briefly before. He and I would flirt when we ran into each other at media parties. But when I asked around about him, word was toxic to the point of ozone depletion. “He cheated on my college roommate with her cousin,” one person reported. An e-mail from another said: “My girlfriend’s sister dated him—till she found out he was sleeping around on her.” Someone else weighed in this way: “Bad, bad news. Dude’s a jerk, with a capital jack-ass.” All right! I’d heard enough: I’d take my business elsewhere.

But the truly shocking evidence came a few months later, after I’d forgotten about him, one late night when I was waiting impatiently for some stuff to come out of the office printer. The first documents to appear were e-mails from the Hack-Ass himself. “What happened between her and me was totally meaningless,” he’d written. “Let me make it up to you”—but that was all I had time to read, before a red-eyed co-worker appeared and plucked the pages out of my hands. He’d gotten to her too!

The whole incident disturbed me. If I could stumble across such damning proof of H.A.’s scarlet behavior, who knew what kind of embarrassing evidence might be floating around out there about me?

Although, of course, in Charlie’s case, I was the one hunting. Once I’d found that his name didn’t ring any bells with my sources, we booked my ticket.

Cut to L.A. My transplanted New York pal—we’ll call her Lucy—took me from the airport to Charlie’s, where we examined the buzzers for a second before spotting the right one. “C. Hollywood/D. Rosenberg,” it read.

“‘D. Rosenberg’?” Lucy said.

“His housemate. I think his name is David.”

“Wait. Charlie went to Harvard? And graduated like seven or eight years before us?”

I nodded.

“So did David Rosenberg,” she said.

“Wait, what? Who?”

“Josh’s older brother.” Josh was some guy who’d just gotten engaged to one of Lucy’s best friends.

“I bet that’s who lives here,” Lucy went on. “Josh’s brother David.”

“No way,” I said. “This is L.A., remember? Not New York. Besides, there’ve gotta be like three billion Rosenbergs in the world. Right?”

Then Charlie appeared. As he and I watched Lucy maneuver her Cabri out of the driveway, he grabbed my hand and kissed it. “Your housemate,” I said. “Rosenberg. First name David? Went to college with you? Brother named Josh?”

“How the hell did you know all that?” he said.

I thought about chasing down Lucy’s car. But then I decided: What the hell, I could wait another week before I started cleaning up my player portfolio. I turned and gave Charlie a smooch.