Mr. Misunderstood

There are two types of people: those who stopped smoking after college and those who started. I am in the latter category (that was a metaphor, Mom). We’re a weird, wild bunch, we who postponed our adolescence till our twenties. We act out to make up for all those nights in high school we stayed in to do homework, but we worry that because we got on the downward path so late, we might miss the exit ramp off.

Mr. Misunderstood, 25, is like me, and he’s scared. He sleeps with questionable women but questions it. “I don’t attract nice girls,” he’s fretting over dinner at Commissary. “The girls I attract, when they were 15, they weren’t virgins.”

“Are you sure you should be complaining?” I ask.

“I worry that I’m getting stunted. I don’t want to be the Guy Who’s Good at Picking Up Trashy Women.”

“Then why’d you ask me out?” He grins and chugs his beer.

Mr. Misunderstood has a puffy black-Irish face, even though he’s Jewish. He was born and raised on the Upper East Side, and after graduating from Skidmore, he moved near his parents and got a job as a book publicist. At night, he went to preppy bars and had one-night stands with what he calls “abrasive, hard-drinking party girls.” It got so bad he moved to Cobble Hill, but he’s revisiting his old haunts tonight in the interest of psychotherapy.

“The last girl I dated was a $1,000-a-night prostitute,” he says with a sigh.

I choke on my risotto.

“I met her at Dorrian’s,” he says. “She was really pretty. We went out a couple times but didn’t have sex because I really liked her and didn’t want to rush it. One night, we went to dinner at Bella Blu, and over salad she told me she was a prostitute. She’s this rich girl who took a job working for an escort service instead of going to college, even though Daddy would have paid. She has a baby and wants it to be the best-dressed baby in Gymboree. She tells me this, and then she says she wants me to be her boyfriend and accept her that way.”

He couldn’t. He went out with her twice more because, he says, he wanted to learn more about it, but eventually he broke off contact.

“I don’t understand what it is about me that makes someone like that think I’m cool,” he whines.

I cock my head and stare at his face. He looks mildly sedated, like a boxer in his last round.

“You look like a thug,” I say. “They think you’re a bad boy.”

“I think it’s because I don’t say a lot. Did you read The Great Gatsby, where he says one of his biggest problems is that he reserves all judgment about people and they take him into their confidence about awful things? That’s me. I haven’t dated any sensitive nice girls from Jewish families, but the Irish Catholic girl with the tattoo, we get along.”

“If you want to meet a sensitive nice girl from a Jewish family, maybe you should go to synagogue instead of bars.”

“When you’re in your early twenties, you get a kick out of the fact that you can walk into a bar and have a drink and meet women. But I don’t belong in those places. It’s like in Bright Lights, Big City. He says something like, ‘You’re not the kind of guy that would be at a place like this at this time of night and what you’re waiting for is to run into a girl who’s also not the kind of person who would be here at this time of night. And you’ll bond over that.’ “

With the hope of Mr. Misunderstood’s meeting a girl who doesn’t belong there either, we go over to American Trash on First Avenue, between 76th and 77th. It’s large with high ceilings, loud eighties ballads, and couples in their thirties. There are traffic signs all over the walls, a golf video game, and a pool table. It’s as close to trashy as the Upper East gets.

I beeline to the bathroom, and Mr. Misunderstood beelines for the bar. When I return, I find him deep in conversation with a longhaired woman with a flattened nose who’s telling him about the coke habit she recently kicked. When she sees me, she says, “Is this your girlfriend?” I shake my head no. Buoyed, she keeps talking. She went to high school at Elisabeth Irwin, lives in a rent-controlled apartment with her mother, and can’t wait for her to die so she can get the whole place. Mr. Misunderstood looks over at me smugly, as if to say, “See?”

Someone calls Elisabeth Irwin’s name, and she goes over to shoot some pool. I notice a cute brunette sitting on Mr. Misunderstood’s other side. She pulls at a beer, pretending to watch TV. I can’t help but admire her craftiness – she slid in beside him without my even noticing. “Could you pass me a straw?” she asks.

He does. She tries to demonstrate a magic trick she’s working on but fumbles it badly. “I learned it from a bartender,” she says. I roll my eyes; this girl’s got less game than Elisabeth Irwin.He introduces himself. She does, too. She moved to the city recently, after graduating from college, and she’s having trouble getting a job. “Where’d you go to school?” I ask.

“Harvard,” she says. I raise a brow. Maybe she’s not so trashy.

He asks her what she studied, and she says psychology. Not trashy. She also did a lot of theater. Trashy. She likes They Might Be Giants. Not trashy. She had a lot of male friends. Trashy.

“I bet you like Monty Python and read a lot of Douglas Adams books when you were younger,” he says. She nods. Not trashy. “And you probably did really well on standardized tests. What did you get on your SAT?”

“Sixteen hundred,” she says. Spic-’n’-span city.

He congratulates her, smitten, and offers to buy her next drink. She says she’ll have whatever he’s drinking, so he orders two Coors Lights. This girl’s so green she doesn’t have a drink yet.

I leave the lovebirds alone and go shoot some billiards (Elisabeth Irwin has mysteriously disappeared). After a while, I see him give her his card. She writes her number for him on a napkin and leaves.

Nu?” I say as he ambles over. “What happened?”

“I asked her if she had a fella and she said no. She said she’d give me a call. I hope she does.” But there’s something strange in his eyes, a worried look.

“What is it?”

“I think she’s really nice, but maybe I’ve gone too far in the other direction. Whatever it is about me that makes me cool with people that are off the hook, people like her make me feel a little scuzzy. I worry that too much evil has rubbed off on me, that I’m not going to be able to talk to her in a way that makes her comfortable.”

“Are you saying what I think you’re saying?” I say, sighing.

“Yeah,” he says morosely as we head out into the night. “I get the sense that she’s just … too … good.”

Mr. Misunderstood