Who's That Girl? It's Rebecca Schiffman!

On the surface, Rebecca Schiffman appears to be a typical privileged New York City kid: She went to private schools (Spence and Dalton), Cooper Union for art school—and at 26, lives with her parents on the Upper East Side.

She’s also a darkly attractive downtown hipster chick who stays out late at the Beatrice Inn, Black and White, Norwood House and Lit. Where she goes is usually determined by whether a friend of hers is DJ-ing, and if they are, she’ll be in the DJ booth drinking free bourbon and Ginger Ale.

Hate her yet?

To complicate matters, she’s warmhearted, upbeat, not at all jaded and very productive. A singer-songwriter, she’s been performing at the Living Room on Ludlow Street. She’s a talented painter, too, with a style reminiscent of Lucian Freud in its tactile depiction of nudity. (She has an upcoming solo show at Petra Projects in Chelsea and will be part of a group show in Vienna this spring.) Plus, she writes for an art blog and is a member of a cool-cat artists’ collective in Red Hook.

I met Ms. Schiffman a few months ago at 4 a.m. She was hooking up with a relative of mine, and the three of us went back to his place and watched a documentary until 6:30 a.m., when I was asked to leave. (“George, we’re going to sleep. Get out of here.”) I dug Ms. Schiffman’s vibe.

We e-mailed in the next few days. I found a picture of her splendid bare ass on the Internet and visited her MySpace page. I was impressed by her songs, so I showed up at the Living Room to see her perform, bought her a drink, then decided to split—something too fragile and innocent about her for me to pursue her further.

A few weeks later, Ms. Schiffman hooked up with a close buddy of mine, whom I’ll call Randy. Soon after that, the three of us were shooting pool on East 15th Street. There was mischief in her eyes. As she sat next to me on the couch, it was impossible to dislike her.

“I’ve sort of been doing the drunk dating thing lately,” she lisped. “I just started drinking, like, a year or two ago. I was afraid of drinking in high school. I smoked pot a bit, but all the preppy kids liked drinking and being obnoxious…. Everybody would always be throwing up all the time and it seemed very unappealing.

“It’s my first year of one-night stands,” she continued. “The thing with Randy is probably the longest thing I’ve had more than a one-night stand in a while. It’s not all sex. I like to go home with guys and see where they live and just meet people. A lot of times, I’ll not even be into a guy, especially older guys. They’ll already be really drunk and begging me to come home with them and be like, ‘I swear I won’t touch you’ and I’ll be like, ‘Uh, all right, whatever.’ So I’ll go home with them and check out their apartment, and then they’ll be kind of awkward, because I’m so innocent and nice.”

Randy was slightly annoyed about the tête-à-tête we were having in the corner. Whatever. The day before, he’d suggested that Ms. Schiffman might want to shave her armpit hair, which she’s had since 2000.

“I’ve had three serious boyfriends who have all kind of wanted me to shave my armpit hair,” she said. “I’ve only known Randy for five days, but he might convince me. We were on the phone the other night and he was making the usual arguments, like, ‘Come on. Then he said, ‘All right, I’ll admit it: Sometimes when I’m looking down at you when I’m on top of you, I want to objectify—and the armpit hair is distracting, it’s ruining it.’ No one’s ever said that; it was so honest, the most honest thing I’ve ever heard. I said, ‘I feel bad that I’m preventing you from objectifying me as your fantasy.’ I said, ‘If you’re nice, I might let you shave my armpits.’ He said, ‘You should probably do that. Tonight would be ideal.’ And I was like, ‘Sorry, I’m getting out of the studio at midnight. Not going to have time to shop for razors.’”

She told me about her blogging. “I think it’s because I am at heart very lonely, and somehow I’m trying to reach out. I feel like all the shit I do is somehow to get guys—but at the same time, any guy that writes me an anonymous fan letter, I’m like, ‘Oh, what a dork.’”

What else goes on in her pretty noggin?

“I think too much … I’m not cynical. I’m an optimistic nihilist. It comforts me that the human race could be wiped out, because I think that human consciousness is what creates good and evil. I have obsessive-compulsive disorder. I hate it when people are like ‘I’m so OCD, I totally have to check the lock like three times.’ Like, fuck you, I almost died. That’s why I’m late everywhere. I’m on loads of medication—Wellbutrin, Luvox and sometimes Risperdal but I try not to take it. I used to cry every day of my life until I started Wellbutrin.”

Does she want to be famous?

“I don’t know about fame. It depends. Sometimes when I’m in a hypo-manic state, I think I’m really awesome and I’m afraid of dying because I feel like there’s work that I need to make that’s worthwhile. Sometime I’ll jog to the kitchen to save time because I gotta be productive, gotta be productive.”

A few nights later I saw her sing at the Living Room. Ms. Schiffman sang very powerful and personal songs, among them “The Rabbit Habit,” about a popular vibrator. Afterward Ms. Schiffman and her posse stopped by Black and White bar, where a friend was DJ-ing. The Olsen twins were there, too. A few nights later she went to Sweet and Vicious for a birthday party for socialite Arden Wohl, another Spence and Dalton alum. The next night, she finished a recording session around midnight in Dumbo and headed to the Beatrice Inn. There, she ran into Randy and it got a little awkward.

Who's That Girl? It's Rebecca Schiffman!