On the Prowl with the Cougar Hunters

The women come to the bar at Abe & Louie’s every Thursday around 7 p.m. in packs of two or three or six, ranging in age from late thirties to early fifties, draped in satin and cashmere and smelling of Chanel and champagne. They order pinot by the glass and dirty martinis with extra olives and they’ve got no plans to eat dinner. They sprinkle themselves in among the older-gentlemanly sorts in pleated slacks, glide past pinstriped bankers expense-accounting lump crab meat appetizers.

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And they are definitely noticed by two guys in their late twenties making their way to the bar. With their open-collar shirts, distressed status jeans, and carefully cultivated facial hair, it’s clear that Matthew Rosa and Patrick Davidson are at least a standard deviation below the average age of those frequenting Abe & Louie’s on a Thursday. But they know what they’re doing.

"The cougars are out tonight," says Davidson (his name has been changed for this story), eyeing the throngs of middle-aged ladies as he and Rosa belly up and order their drinks. "This could potentially be an epic night." The bartender sees the same thing. Surveying the crowd, he sizes up his clientele. "The women here are looking for one of two types: old and rich or young and handsome," he says, taking an order for a cosmo. "And if it’s just a one-night thing, they’ll take young and handsome every time."

For Davidson and Rosa—and the rest of a growing number of Boston men embracing the role of self-described cougar hunters—Thursday nights at Abe & Louie’s are a no-brainer. If you’re a younger guy angling to spend your evenings in the company of older women, few settings are more target-rich: The steakhouse bar has been rated by the readers of Urbancougar.com as one of the top cougar dens in town. And there’s a lot of competition, as all across the city—in the kinds of martini-heavy, leather-and-oak joints preferred by the upwardly mobile—romantically aggressive middle-aged women are out in force.

The most dedicated adhere to the sort of fixed social patterns of college campuses: The night before the Abe & Louie’s spot in the rotation, they take over the Warren Tavern in Charlestown. On Friday, they move on to Grill 23. Saturday is Jurys.

What a time it is for the cougar scene! What was once just a punch line to jokes involving Demi and Ashton is now a bona fide cultural phenomenon whose manifestations are legion: Eva Longoria’s character doing her young gardener on Desperate Housewives, a sudden outpouring of dating guides for older women (one titled, appropriately, Move Over, Mrs. Robinson), a Cradle Robbers series of novels, and an online dating site (GoCougar) to go with the Urbancougar guide. Somewhere along the way, the "cougar" moniker has been snatched from the jaws of derogatory snark, given a glossy feminist makeover, and come out an empowerment label to be brandished with pride—a way for women to own both the word and the lifestyle associated with it. You’ll even meet fashionable Boston women in their early thirties joking about being in their CIT (Cougar In Training) years.

Hence the development that in this city the formerly rare blend of young man et older woman has become, if not omnipresent, then at least intensely familiar. Should we be surprised? Boston is dense with accomplished, urbane women—the sort with money and status and options when it comes to guys. These days, those women simply want to take advantage of a perk previously exclusive to men: dating much, much younger.

But empowerment and ubiquity have led to an unforeseen outcome. Younger men (ever the prescient pioneers of new ways to get ass) are taking notice of all this cougar pride and doing more than just making themselves available to plucky cougars: They’re now seeking these women out. And so it is that taking home an older lady—once seen as a desperation move to be kept secret—has become a spirited and celebrated pastime for a certain type in the male population born between 1975 and 1985. And that, as you might imagine, is putting a big twist on the dynamics of a night out in Boston.

As much as they like to wax poetic on what they do at night, Rosa and Davidson hate talking about what they do by day. Davidson says he works in the financial world, and prefers to leave it at that. Rosa does paralegal work and plays a lot of high-stakes poker—both of which he makes sound like side ventures. His real gig, he tells me, is "banging older chicks who pay for my stuff." I laugh. He clears his throat. He’s not kidding.

Rosa says he’s got two women he keeps closer than others. One, an interior decorator with a condo on the waterfront, regularly has him over to share intimate moments during the day. The other, a doctor on the South Shore, bought him an iPhone, pays for his cell plan, and picks up his membership at the Sports Club/LA. The ease with which he’s keeping the nonexclusive attentions of these women—both attractive, successful professionals—recently sparked an idea. Utilizing the very American intuition that he might have an exploitable talent, Rosa has secured the domain name cougarhunter.tv. He says he’s shopping a reality show, creatively named Cougar Hunter, in which he would travel across the country in an RV, picking up women at various spots along the way. "I don’t know what it is," he says. "These chicks just seem to love me."