On the Prowl with the Cougar Hunters

You’ve heard of cougars—those empowered women with an appetite for younger men. Well, now meet the cougar hunter. He’s that opportunistic twentysomething infiltrating the classy Back Bay bar, his sights set on a middle-aged conquest. And with him on the loose, the rules of Boston’s dating scene are turned upside down.

cougar

Photo by Tanit Sakakini

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.

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.”

Lest you think any twentysomething can just hop on over to the nearest cougar watering hole and start making time with a sophisticated older woman, you should know that there are some things a would-be cougar hunter must keep in mind. Chief among them are matters of aesthetics. Rosa’s dirty-blond hair is thoughtfully shaggy, his muscles are gym-enhanced, and the stubble on his face is an intentional three days old. He resembles an actor playing the role of an out-of-work actor. He appears perpetually half-asleep. Davidson, meanwhile, has a lankier frame and wears his hair closely cropped. He has the look of a former middleweight boxer turned upscale lounge doorman, his face frozen in the half-smirk of someone listening to a joke he can’t quite hear. Neither would be mistaken for Clooney (or more applicably, Kutcher), but still, they’ve got enough in the looks tank to pass muster.

Attire is also important. The cougar hunter walks a fine line with clothes: He needs to be noticeably different from the older guys so he can demonstrate and exploit the advantage of his age, but he must also avoid marking himself as a frequenter of the cheesier Faneuil Hall bars. This means bold colors and patterns on otherwise classy button-down shirts (which are often unbuttoned past the point of logic), and the aforementioned distressed (but dark, always dark!) status jeans. He also needs to blend in with the tony crowd he’s infiltrating—pushing the limits without going so far as offending—which requires covering those stylish shirts with sport coats and sliding on leather loafers. Rosa, the more daring of the two, sometimes accessorizes with a woman’s headband, which he claims is a sure-fire conversation starter. “My look is very trendy and unique,” he says. “I’m not sure everyone could pull that off.”

A pedigree also helps, whether invented or real. For the cougar hunter, dropping a home address on the flat of Beacon Hill or in parts of the Back Bay or the South End can suggest a certain It factor, especially with women from the suburbs. “I like to tell cougars that I bought Johnny Damon’s condo in Back Bay when he signed with the Yankees,” says Chris, 27, a banker. “I’m bullshitting, of course, but as a rule, cougars love Johnny Damon. And by the time they get back to your place, it’s pretty much a moot point.”

That Chris’s fib also suggests disposable income on par with Johnny Damon’s is not to be overlooked, either. The impression of cash is always helpful; at the very least, a would-be hunter needs the financial wherewithal for some free spending at the bar. “Although these chicks might be really rich and eventually buy you gifts, they are still women,” says Rosa. “So you’re probably going to have to buy them some drinks. It’s not quite enough for us to just go up there and look pretty. Plus, they’re hanging out at nice places, so they expect you to be used to that sort of thing.” Beyond being able to afford a few $10 glasses of wine, though, the cougar hunter needn’t sweat his cash situation too much. “If they’re exclusively looking for dudes with money, then they’d be with those older dudes,” Rosa says, pointing to the 40- and 50-year-old guys shuffling their feet near the bar at Abe & Louie’s, attempting to hold on to what used to be their turf.

But what matters most, say the hunters—clichéd as it sounds—is the proper mindset. Confidence is a turn-on, yes, and the ability to project an aura of maturity is good, but the hunter must also possess a sort of morally casual pragmatism and a very real understanding that these are women with histories and backgrounds involving plenty of stuff for which the psychological arsenal of the typical twentysomething guy is poorly equipped. There’s a need for at least a topical application of sensitivity, which makes the whole pursuit feel almost redeeming. “It’s important to know how to deal with recent divorcées and single mothers,” Rosa says. “And it doesn’t hurt to be good with kids.”

As nine o’ clock rolls around at Abe & Louie’s, sobriety’s engines begin to stall out. Conversations are getting louder and happening at increasingly close range. Even though three or four rival hunters have begun to mix themselves in nearby, Rosa and Davidson dismiss their competition. The place has become a tangle of sequined tops and Tanqueray Ten and tonics, giving cause for the two to upgrade their scoring potential from strong to quite strong. “If you’ve got the right thing going,” says Rosa, who believes that he does, “it’s like a lay-up on an 8-foot hoop.”

For the women I talked to, the road to cougardom isn’t marked with angsty fits of self-evaluation or soul-searching about why they’re gravitating toward younger guys. It’s the opposite—a move away from all that introspection. They are, to borrow a phrase, just looking for a good time. “I wasn’t aware of the rule that says, as a woman, once you reach a certain age you can’t have fun,” says Sandy, an attractive, athletic blonde at the bar in a sleeveless black dress. She’s possibly in her mid- to late forties (she refuses to say exactly). “This is a chance to cut loose and not care about pretension. I always date younger men. I’m convinced they’re the only ones who can keep up.”

I introduce her to a friend of mine, a guy I’ll call Sid. He’s a financial analyst in his early thirties who I was surprised to spot here on cougar night. The two immediately begin to flirt, he playing the “I never really come to these places” card and she playing the “I know you’re bullshitting but I think you’re cute” card. After several drinks, they share a passionate tongue kiss outside in her parked SUV. Several days later, in response to my request for details and his opinion on how makeout techniques might differ between generations, Sid writes back with: “As a rule, kissing styles are generationally agnostic. Oh, and it’s entirely possible that Sandy drives the same Lexus SUV as my mother.”

According to the cougars being preyed on by the Sids of Boston, this is not an uncommon ending to an evening—a reality about which they couldn’t be happier. “I’ve definitely noticed an increase in the boldness of younger guys, especially in the past year,” says Amy, a teacher in her late thirties who lives in a suburb west of the city. “There are more [younger men] at the upscale bars, they’re more forward than they used to be, and they seem to be actively seeking us out.” She pauses, then laughs. “Not that I’m complaining. I don’t think it’s ever a bad thing when more guys are paying attention to you.”

Amy likes dating younger guys; she feels they’re easier to get to know. “Single men my age tend to have a lot of unnecessary baggage,” she says. “I don’t hold that against them—everyone has baggage—but younger guys seem less concerned with airing it out. They just want to have fun.” And all the newfound attention doesn’t surprise her at all. “We take good care of our bodies, we work hard, and we look hot,” says Amy. “It’s about freakin’ time we become sought after.” Adds the dental hygienist at my dentist’s office in Wellesley, “Women have seen men our age going out with 25-year-old girls for a long time. And there’s only so many times you can have a ‘girls’ night.'”

 

It’s half past 11 and Rosa hasn’t moved beyond Red Bull. He doesn’t like to be drunk when he talks to cougars, says it messes with his game. Plus, he says, “it’s hard to keep track of the chicks.” (Davidson, for his part, does not subscribe to this strategy. “I’m getting really shit-faced,” he says.)

A pair of women we’d seen on our way in begin staring unflinchingly in our direction. The dynamic already feels different: There are no coy looks, no sidelong glances, no halfway stares. The guys look over invitingly and then pretend to watch the Celtics game on the television above the bar while keeping their bodies turned toward the women. It’s all the enticement the ladies need. They slide/lurch forward—brushing past annoyed older men as they introduce themselves to the guys.

The one in the red dress touches Rosa’s messy hair and calls him pretty. Her friend has teeth the color of merlot, and a Jokeresque grin that’s been stamped by her wineglass around the edges of her mouth. She swears she’s seen Davidson before. “Beacon Hill, definitely,” she says, her wandering hands working their way over his chest and arms. “Nantucket, yes. Maybe the Chatham Bars Inn?” Davidson’s not so sure, but plays along. As he does, I forget the soft light of the wood-paneled room and the necktied barkeeps and I realize that I’ve seen the same giddy courtship scene play out among 19-year-olds in Cancun. When I share this thought with Davidson, he agrees. “Dude, it’s like adult spring break for these chicks,” he says, as his new friend rubs his shoulders, “except they do this every week.”

This is confirmed by the staff at the once-staid watering hole. “Oh yeah, after nights like this, when the restaurant clears out, I’ve seen people locking themselves in bathrooms, doing stuff around corners,” says our bartender friend. “It’s pretty nuts.”

For the young men involved, it’s all very alluring, this tableau of lusty tongue kissing and expensive cocktails. And they say it’s refreshing, too, for them to find women who know what they want and why they want it, and who refuse to play games. But you haven’t been reading closely if you’ve failed to notice a vapid quality to all this as well. Scratch anywhere near the surface, and the spoils of the hunt look rather shallow. Most guys get this. Even for its most dedicated practitioners, the game feels a lot like looking for love at summer camp: It’s intense and crazy and more than a little awkward. And in the end, there’s an almost perfect chance that nothing’s going to last.

Of course, that’s totally fine with Rosa and Davidson. As the crowd dwindles, phone numbers that will never be used are exchanged. Kisses are shared, but nothing more. As they leave the bar to hop into a cab, Rosa explains why they let the evening’s quarry get away. “Those chicks were too hammered, it was too much of a lay-up,” he says. “I just couldn’t do it.” He directs the cabbie to the Liberty Hotel, a place with “iffy cougar potential,” and looks back at a gaggle of cougars spilling blissfully out of the bar.

“Plus,” he says matter-of-factly, “they just weren’t that hot.”

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