For handsome twentysomething men on the make, the ideal Manhattan woman is neither the supermodel nor the stripper but a new breed of biddy: the dirtysomething. “She’s a woman in her thirties who likes to get dirty,” explains Matt, a 24-year-old who works at a real-estate-investment firm and looks like Tom Cruise. “She broke up with her boyfriend of five years at age 32, she thought they were getting married, and she doesn’t know what to do. So she says, ‘Fuck it. I’m going to go on this faux-independent spree for a while.’ ”
Matt and I are at Dorrian’s on a cold December night along with his buddy Roy, 23, an investment banker who looks like Richie Rich. Matt first heard the term dirtysomething from his 35-year-old boss, who had been on three dates with dirtysomethings, all of whom wanted to draw him a bath.
Matt’s own most thrilling dirtysomething experience involved not one but two. He was on a ski trip in Tahoe. One night in the lodge, two attractive women pulled out video cameras and began acting up for the camera. “One’s dirty-nine, the other’s dirty-six. One had her boyfriend there, and they started kissing and grinding for the tape.”
There was a group of young women in the lodge, all wearing T-shirts that said BAD GIRL, and the dirtysomethings urged Matt to dance with them. “Next thing you know,” he says, “I’m lap-dancing, they’re stripping my clothes off, and we’re doing body shots. I got down to my underwear and made $80 in tips.”
At dinner that night, one of the videotapers, Angie, invited him back to her room with a shyer girlfriend, Tina. The three hopped in a car to the hotel, and the women went into the bathroom. “It’s one of those moments when I want to high-five someone but I can’t,” he recalls. “So I do the only thing I can do: dial the front desk. This guy picks up. I say, ‘Dude, you don’t know me, but I’m the guy that just walked in with those two thirtysomething women.’ He says, ‘Yeah?’ I say, ‘I’m about to have a motherfucking threesome!’ He says, ‘That’s awesome. My girlfriend works here, I can be there in ten minutes. We’ll bring some Cristal.’ I’m like, ‘You know what, bro? I appreciate the offer, but this is one plane I have to fly by myself.’ ”
The threesome itself was pretty tamethere weren’t any condoms so it was mostly oral, them to him. He dated Angie a few more times, until she turned “dorty” and stopped calling him. When they did go out, Matt remembers, Angie insisted on paying and would get angry if he tried to: “In general, the guy has to be more forward, but here the woman pays for everything. She holds the door.”
As dozens of collegiate girls stream into Dorrian’s, Roy is oblivious as he leans forward to tell me about his first dirtysomething: Ghost Mom. He was living with a roommate on the Upper West Side, and the day they moved in, they noticed a paper ghost on the door of the apartment across the hall, left over from Halloween. Eventually, they met the occupants, a thirtysomething woman and her 7-year-old son. “We’re like, ‘A hot mom. Awesome,’ ” he remembers, “and we start referring to her as Ghost Mom.” Whenever they came home drunk, they would move the ghost to a different place on the door.
One weekend, Roy’s roommate went away. Roy was going down in the elevator when Ghost Mom got in. He asked where her son was; she said, “With his father.” Turns out she was divorced. “So I said, ‘You know your name is Ghost Mom, right?’ She was Czech and had a little bit of an accent, and thought it was some weird English expression. I explained it and she said, ‘Have you been moving the ghost? My son’s freaked out.’ ” They laughed about it and wound up walking to the store together. “I start thinking, Kid’s away for the weekend, Ghost Mom’s pretty hot. I’m like, What a story for my roommate.” He asked if she had eaten dinner yet, she said no, and he invited her to Carmine’s. He plied her with wine, she started flirting, and when they got back to their hallway, he moved in for a kiss. “Immediately, we went into her place. It was all business, crazy. Scored, no problem. The sex was good, but you could tell she was a little out of practice. I don’t think she had had sex since the divorce. She kept asking, ‘Is this good?’ I was like, ‘Relax, I’ll handle it.’ ” The affair went on for the rest of the summer, whenever her son was away.
Though the stereotype of an older woman is Mrs. Robinson, a cool, collected dominator who instructs men on how to please her, Matt and Roy say that what’s most surprising about dirtysomethings is their sexual generosity. “With dirtysomethings, I’m being serviced,” says Roy. “However I want it, wherever I want it.” The only downside to dirtysomethings, Roy says, is the obvious one: “Bottom line, I wake up with a 39-year-old next to me. That’s a reality check.”
Both guys like the idea of being “catches.” Like most twentysomething guys with an inflated sense of self-worth, they seem to define prowess according to stamina, not skill. “There’s definitely the Sex and the City image of the thirtysomething women sitting there the next day at brunch,” says Matt, “and you want them to be the envy of the other three girls at the table.”
“It’s a power thing for me,” says Roy. “I can completely throw caution to the wind in terms of how I treat them because I’m in such a dominant position, just by age.”
With all their eagerness to please, dirtysomethings can wind up spoiling a guy, whether or not they intend to. “I went out with a 34-year-old last week,” Matt says, “a girl who usually dates older men because she likes being pampered. We hung out for two hours, and I had to make more effort than I wanted to. She e-mailed me the next day to say thanks for dinner. I thought, Then why didn’t you pay?”