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.

“I have not done this in a while—like I forget how this [dating] works,” she told me a few days later. We were having lunch at Gotham. She was wearing a white T-shirt under a vintage Valentino jacket, ABC jeans and motorcycle boots. She went on: “I thought it was a little weird that we had not talked all day and we ran into each other at Beatrice.... We were sort of grinning at each other and he said, ‘I think you should sit down with me.’

“I’ve always been attracted to the obnoxious class clown,” she continued. “And Randy’s totally that guy that you’re kind of embarrassed for, but also psyched that he’s dancing like a transvestite performer. It seemed like he was looking in the mirror at himself dancing and doing moves.”

That night, she said, Randy had wanted to leave and have sex while Ms. Schiffman wanted to stay. “He kept saying, ‘I wanna F you.’ He was wasted and I wanted to get drunk—not be sober with him like that—and I was having fun dancing.”

At 3 a.m. Randy paid his tab and the lovebirds piled into a cab. “Randy is lying down, and he starts to open his fly, and he really wants me to give him a blow job in the cab,” Ms. Schiffman recalled. “I said, ‘No, I think that’s really disrespectful to the cab driver, and I’m not going to do that. You might as well just zip up your pants.’”

They picked up some fish tacos then stomped up the stairs to Randy’s East Village apartment. All of a sudden she heard a man yelling; it was the downstairs neighbor.

“I go over to the door, and he’s sort of pushing Randy, trying to work his way into the apartment, and he’s kind of heavy with a long red ponytail and a mustache,” she said. “He was saying, ‘I told you a thousand fucking times! I can hear your every footstep at 4 a.m.!’ and it was pretty scary. I thought, He’s not going to hit a girl. So I put myself between them. And he shoved me really hard out of the way and was grabbing Randy and he said, ‘I’m going to fucking kill you.’ And his wife comes up the stairs and says, ‘We don’t live the party lifestyle, I have to get up in four hours!’ And she’s like, ‘We know you’re a fucking asshole and I hear you come in at 4 a.m., I hear your girlfriends’—that was supposed to be a little stab at me—and she said, ‘Get carpeting—it’s in the lease!’”

After the neighbors left, they watched TV in bed.

“We didn’t have sex,” she said.

When she was a youngster, Ms. Schiffman had a nanny from Barbados who would try to convert her to Christianity. She played the cello, took ballet classes, was on the gymnastics team at the 92nd Street Y and went to Hebrew school three times a week. Her parents worked for IBM; her dad is also a Rabbi.

She received paints for her 10th birthday, and from the beginning her parents were very honest with her. “If I made a painting, my mother would be like, ‘Hmmm, it’s not so good,’” she said. “I think I’m good at drawing because they would always be like, ‘That’s not really correct.’ They’d never be like, ‘Oh, good job!’ But even now, when I make work, my mom will be like, ‘Hmmm, not really my kind of thing.’ I’m like, ‘I wasn’t asking you if it was your kind of thing. Can you just look at it, within my work, and say how it measures up?’”

In ninth grade she transferred from Spence to Dalton, where it was “all jocks” and “Jappy” girls. She hung out with art and music kids, dyed her hair and sewed band patches on her backpack. Ms. Schiffman and her friends would look around the classroom and make lists of how everybody in the class should die. “We would come up with three ways to kill someone,” she said. “One would be kind of fucked up, the next one would be pretty nasty, and the next one would be like, holy shit, that’s, like, horrendous.”

When she was 15 she fell in love with a senior named Nick, a punky skateboarder whose parents were up on the Forbes 400 list. She was too young for Nick but they became friends. They’d walk to school, watch The Simpsons at 5 p.m., take his dog for a walk, then watch The Simpsons again at 6.

“I now realize that being in love then was intertwined with depression,” she said. “I didn’t have the capacity to be happy. So I would try to find it from someone else. Ever since I’ve been on Wellbutrin, I’m always fundamentally happy and I can’t fall in love that way, which is good. But it’s less intense.”

She did finally get to make out with him. A few years later he tragically drowned while diving in Bali. She spoke at the funeral.

She thinks her OCD began at age 4. She received a Samantha doll as a gift and soon became terrified of it. The doll would sleep in its own little bed, at the foot of Rebecca’s bed. Every time she walked in and out of her room, she’d have to run past Samantha because she thought the doll was going to swipe at her. She slept with two wrenches under her pillow. Every night, she would have to kiss Samantha once before going to bed (“I had to, or it would be unhappy”) and looked under its blanket to check if its nails had grown.

“People were like, ‘Oh, get rid of her, throw her out,’” she said. “But if you’ve seen any of those movies, if you get rid of ’em, they will come back and they’ll seek revenge.”

The OCD rituals continued. She would always be late to school even though she lived a block away: She’d get to a lamppost and be unable to decide to walk to the left or the right of it. If she went one way something could happen and the other way something else could happen. She’d marvel at the people walking right by the lamppost, undeterred.

At Cooper Union, it got worse.

“I couldn’t leave my bed,” she said. “I lived in a suite with four other girls, and I would look at them with envy as they were doing the dishes, like, Look at them scrubbing that dish without a care on the world. It’s so easy for them. Because for me, to take just 20 steps to get to the bathroom, would take half an hour because on the way I’d be like, Something about the way I put my foot down there felt wrong. So I’d have to keep walking around the floor until I somehow solved it, like tuning in to the universe, because I can’t accept not having control over things.”

During her sophomore year, she decided to get rid of Samantha. She posted an ad on Craigslist in the free section, because she thought if she got money for the doll, it would be “blood money.” The next day, she stuffed the doll, its bed and belongings into a bag and handed it off to the first person who replied, a woman whose niece had a doll collection.

“So I gave it away and now I love my apartment and I’m so happy there,” she said. “Life is so much better now. It’s like, why did I have that doll for 10 years?”

We finished our lunch at Gotham. I asked for the check and she went to the ladies’ room. On her way back, her OCD acted up and it took her a while to mount the stairs. Walking west she talked about a recent night with Randy. It was really late and she wanted some lube and was convinced she could find some at a deli.

“So we were walking down Avenue B and he was so embarrassed,” she said. “I made us go to every deli and I was like, ‘Excuse me, do you have any K-Y jelly?’ And they were like, ‘What?’ And I was like, ‘You know, for sex?’ Apparently delis just don’t carry lube.”

We took the subway to Brooklyn. We got off at Smith Street and started walking to Red Hook. I learned that if she sees a cigarette butt on the sidewalk, she might have to get down on the ground to study it before she can move on.

We arrived at an enormous building that used to be a printing press. Dustin Yellin, a painter whose works sell at the Robert Miller Gallery, and his Park Avenue-bred girlfriend Charlotte Kidd, a photographer, bought the place and are converting it into an art studio and living space.

Ms. Schiffman’s paintings sell for $850 to $1,400. She began showing me some of her work. Pubes was a close-up of an ex-boyfriend entering her. Next, a series of self-portraits she did in Paris last summer, one of which she made after taking too many antidepressants. “I love Wellbutrin, but I was like twitching and short of breath and didn’t figure it out until like six in the morning,” she said. “So I called my dad in New York and asked him to talk to me, calm me down. I still couldn’t sleep, so I did this painting. “

She showed me another watercolor, similar to Pubes.

“The other one’s better, but the penis is much better in this one,” she said, adding that a gallery owner in San Francisco agreed. “He said the cock looks meatier and I was like, he’s right. This is the meatier cock. It has more presence.”

She showed me a painting she titled Endearing Moment No. 1, which depicts her ex-boyfriend Javier masturbating to porn on an Apple computer.

“I just feel it’s an image people can relate to,” she said.

Next she showed me a series of portraits she’s done of Woody Allen. She and her brother Jonathan (to whom she is very close and who is the music director and conductor of the Avignon Opera) would recite scenes from Hannah and Her Sisters on family trips.

“I’ve always been sympathetic toward him with the Soon Yi thing,” she said. “I just feel like he’s a great contemporary example of a decadent figure … and so far in the head that his body is sort of in decay and not very healthy. And the thing with Soon Yi is sort of decadent, you know, just go for it.”

She said Randy hadn’t called her in two days and she felt lonely, so we hung out that night.

A few nights later the restaurant Elaine’s was celebrating its 45th anniversary. Ms. Schiffman and I went, in case Woody Allen was there. Sure enough he was, chatting with Elaine Kaufman at the bar. We arrived just as he was walking out. I did a quick introduction. She told him that her paintings of him are going to be in an exhibition in Vienna. Mr. Allen said he’d like to see the portraits and told her how she could contact him.

After dinner the two of us stepped outside to smoke a joint, then decided to head to her apartment. It was potent stuff. “I kind of feel like it was a big check mark on stuff to do in life,” she said of meeting Mr. Allen. “Seriously, I feel like I can rest a little more easy now.”