My Old Lady

For handsometwentysomething men on the make, the ideal Manhattanwoman is neither the supermodel nor the stripper but anew breed of biddy: the dirtysomething. “She’s a womanin her thirties who likes to get dirty,” explainsMatt, a 24-year-old who works at areal-estate-investment firm and looks like Tom Cruise.“She broke up with her boyfriend of five years at age32, she thought they were getting married, and shedoesn’t know what to do. So she says, ‘Fuck it. I’mgoing to go on this faux-independent spree fora while.’ ”

Matt and I are at Dorrian’s on a cold December nightalong with his buddy Roy, 23, an investment banker wholooks like Richie Rich. Matt first heard the termdirtysomething from his 35-year-old boss, whohad been on three dates with dirtysomethings, all ofwhom wanted to draw him a bath.

Matt’s own most thrilling dirtysomething experienceinvolved not one but two. He was on a ski trip inTahoe. One night in the lodge, two attractive womenpulled out video cameras and began acting up for thecamera. “One’s dirty-nine, the other’s dirty-six. Onehad her boyfriend there, and they started kissing andgrinding for the tape.”

There was a group of young women in the lodge, allwearing T-shirts that said BAD GIRL, and thedirtysomethings urged Matt to dance with them. “Nextthing you know,” he says, “I’m lap-dancing, they’restripping 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 thewomen went into the bathroom. “It’s one of thosemoments when I want to high-five someone but I can’t,”he recalls. “So I do the only thing I can do: dial thefront desk. This guy picks up. I say, ‘Dude, you don’tknow me, but I’m the guy that just walked in withthose two thirtysomething women.’ He says, ‘Yeah?’ Isay, ‘I’m about to have a motherfucking threesome!’ Hesays, ‘That’s awesome. My girlfriend works here, I canbe 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 tame—thereweren’t any condoms so it was mostly oral, them tohim. 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 getangry if he tried to: “In general, the guy has to bemore 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 abouthis first dirtysomething: Ghost Mom. He was livingwith a roommate on the Upper West Side, and the daythey moved in, they noticed a paper ghost on the doorof the apartment across the hall, left over fromHalloween. Eventually, they met the occupants, athirtysomething woman and her 7-year-old son. “We’relike, ‘A hot mom. Awesome,’ ” he remembers, “and westart referring to her as Ghost Mom.” Whenever theycame home drunk, they would move the ghost to adifferent place on the door.One weekend, Roy’s roommate went away. Roy was goingdown in the elevator when Ghost Mom got in. He askedwhere her son was; she said, “With his father.” Turnsout she was divorced. “So I said, ‘You know your nameis Ghost Mom, right?’ She was Czech and had a littlebit of an accent, and thought it was some weirdEnglish expression. I explained it and she said, ‘Haveyou been moving the ghost? My son’s freaked out.’ ”They laughed about it and wound up walking to thestore together. “I start thinking, Kid’s away forthe 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, andhe invited her to Carmine’s. He plied her with wine,she started flirting, and when they got back to theirhallway, he moved in for a kiss. “Immediately, we wentinto her place. It was all business, crazy. Scored, noproblem. The sex was good, but you could tell she wasa little out of practice. I don’t think she had hadsex since the divorce. She kept asking, ‘Is thisgood?’ I was like, ‘Relax, I’ll handle it.’ ” Theaffair went on for the rest of the summer, wheneverher son was away.Though the stereotype of an older woman is Mrs.Robinson, a cool, collected dominator who instructsmen on how to please her, Matt and Roy say that what’smost surprising about dirtysomethings is their sexualgenerosity. “With dirtysomethings, I’m beingserviced,” says Roy. “However I want it, wherever Iwant it.”The only downside to dirtysomethings, Roy says, is theobvious one: “Bottom line, I wake up with a39-year-old next to me. That’s a reality check.”Both guys like the idea of being “catches.” Like mosttwentysomething guys with an inflated sense ofself-worth, they seem to define prowess according tostamina, not skill. “There’s definitely the Sex andthe City image of the thirtysomething womensitting there the next day at brunch,” says Matt, “andyou want them to be the envy of the other three girlsat the table.”

“It’s a power thing for me,” says Roy. “I cancompletely throw caution to the wind in terms of how Itreat them because I’m in such a dominant position,just by age.”With all their eagerness to please, dirtysomethingscan wind up spoiling a guy, whether or not they intendto. “I went out with a 34-year-old last week,” Mattsays, “a girl who usually dates older men because shelikes being pampered. We hung out for two hours, and Ihad to make more effort than I wanted to. She e-mailedme the next day to say thanks for dinner. I thought,Then why didn’t you pay?”

My Old Lady