On the Prowl with the Cougar Hunters

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.'"