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Boston Magazine

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.

By Kevin Alexander

Page 1 of 3

Photo illustrations 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."


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User comments

Well written!
Apr. 30, 2008 at 6:12 PM
Posted by Dan Cournoyer
If you think Boston has some hot Cougars (and they certainly do) you need to bring that bus out here to San Diego...
This is not yours...
May. 1, 2008 at 12:49 AM
Posted by Anonymous
This isn't your material- I read a blog a couple of weeks ago that had the same thing...same sites, etc. At least give the guy credit!
This is not yours...
May. 1, 2008 at 12:49 AM
Posted by Anonymous
This isn't your material- I read a blog a couple of weeks ago that had the same thing...same sites, etc. At least give the guy credit!
Please note
May. 1, 2008 at 7:59 AM
Posted by Paul Flannery
That's a serious charge to be leveling. Perhaps you missed this notation in the sidebar: All cougar-hunter reviews excerpted from Urbancougar.com.
LOOK
May. 1, 2008 at 8:44 AM
Posted by Anonymous
Look at this- www.dailyknowledgedrop.com All references, sites, etc are from it
PLAGERISM!!! Your A$$ is GRASS :)
May. 1, 2008 at 8:38 AM
Posted by Annie Mullen
Darling, I'm not sure who you're trying to fool here...but your Cougar Hunter article is not your own material. Perhaps you should have referenced www.dailyknowledgedrop.com as the source for the Cougar Hunting tips & tricks you have claimed as your own.
How Sad
May. 1, 2008 at 8:34 AM
Posted by Deborah Gauthier
Sad lonely women who have lowered themselves to the status of flesh eating males. Younger males offering themselves to be devoured, all to what end. Is anyone really getting their needs met? Lust without love will eat you alive from the inside out. Bon Appetite'
Not original....
May. 1, 2008 at 10:24 AM
Posted by OB Rock
Wow!!! This is intersting I have read the same concept and information on another blog. Your material is faulty. You need to give the author at http://www.dailyknowledgedrop.com/2008/04/cougar-drop.html, his dues. Next time you decide to plagerise, dont make it so obvious. Plus the cats you talk about sound like a bunch of Homos. Especially that Rosa guy...he wears womens head bands. Wow, he is a real WINNER!!!
YOU CANNOT BE SERIOUS
May. 1, 2008 at 10:39 AM
Posted by Christina R
WOW. Nothing to write this month? I have an idea for next month- "An Exploration into why Women Become Lesbians" Answer: The subjects of this article. Matt and Pat (how fitting they should rhyme)- If we were the last people on earth I would rather take my chances with extinction, than to hook up with you or someone like you. FYI Matt, I checked you out on facebook because I HAD to. You're a fruit, and ANTI-everything a real woman would want. I'm sure you like Peach Bellinis like the chick you are. I'm disgusted.
seriously?
May. 1, 2008 at 11:11 AM
Posted by Anonymous
1- www.dailyknowledgedrop.com is the originator of this story - nice job using someone elses material 2- anyone that actually knows matt would never write in such a positive tone about him 3- for a blog, great entertaining info but for boston magazine, come on guys, get it together
The original blog
May. 1, 2008 at 11:27 AM
Posted by Anonymous
http://www.dailyknowledgedrop.com/2008/04/cougar-drop.html#links Are we sure Ron Borges didn't write this article?
Faulty Charges
May. 1, 2008 at 11:27 AM
Posted by D. P.
I have read the dailydrop blog that you are saying Kevin plagerized, and find your arguement faulty. The dailydrop breifly touches on the cougars' hunting and mainly gives statistics and references to the actual cat and drugs. Did it ever occur to you that the guy who did the dailydrop took some information off the urban cougar hunter website? Or perhaps he googled it and came up with the same commom knowledge as what everyone else has in their articles. When you read multiple articles on the same subject you are bound to find some information as the same, because it is common knowledge not because it is plagerized. Besides Kevin's is a story of a night out with cougar hunters and the drop was about cougars. You can find a lot of the information from the drop in other articles if you google it. It is called common or public knowledge, NOT plagerism. Before articles are published the company has people reserch the topic to make sure that nothing is plagerized and that the pictures
Continued
May. 1, 2008 at 11:44 AM
Posted by D. P.
they are using are not copywrited. This is why they mentioned the urban site. They do not refernece blogs since bloggers get their inforamtion else where, such as google and yahoo, and are not the orignal holder of the information.
WRONG!!!
May. 1, 2008 at 12:02 PM
Posted by Christina R
Ok-"D.P." I think the main point of the people saying the article was plagerized is NOT to say he took sentences, paragraphs, in full out of the blog. I think plagerize was taken out of context and misused. I am guessing the readers feel its un-original content was reproduced to describe a night out with these losers drinking Red Bull at a steakhouse. We are now at our original point- the ideas and spin to this is un-original, as the knowledgedrop.com site already stated what Kevin did, MINUS go out with them. After reading this, most would agree staying clear of these sleezy roaches is a great idea!
I AM THE DKD
May. 1, 2008 at 12:18 PM
Posted by P A
Matt and Pat- I am guessing that somewhere along the road to his own success your fathers might have left you behind, rendering you the orphan known as failure. What I think you really mean is you drink Red Bull because nobody offers you a drink. So, continue sipping, and feeling good about having "sponsors" similar to an orphaned third-world child eating the sticky, bleached, UNICEF rice that still looks better than your hair blemished by what looks like a brawl between Courtney Love and Gia involving a curling iron, bleach, and a power outlet.
i heard...
May. 1, 2008 at 12:51 PM
Posted by Chance Roberts
28-35 : CIT or Puma 35-Menopause : Cougar Past Menopause : Lioness Super hot Cougar (read:Demi) : Jaguar
What a Dickhead
May. 1, 2008 at 1:19 PM
Posted by Anonymous
I used to work with the woman from the South Shore's ex husband. He will be very amused by this article. Rosa is such a loser.
jealousy
May. 1, 2008 at 1:38 PM
Posted by Matt Rosa
wow such jealousy!!!! I guess I am a loser!!!! Ha...
Why be anonymous??
May. 1, 2008 at 2:00 PM
Posted by Anonymous
Instead of being anonymous and talking sh*t about someone why don't you come down to the scla tonight and say it to our faces tough guys. You apparently know who we are so do something about it, chumps.
Haters
May. 1, 2008 at 2:16 PM
Posted by Patrick Davidson
These comments are pretty amusing. Keep the hate mail coming. I can say, in Kevin's defense, that he did not plagiarize.
Jealousy
May. 1, 2008 at 2:21 PM
Posted by Anonymous
The jealous people responding must be the guys in the corner of the bar watching our crew pick up every single good-looking girl in the bar (young and old). Maybe bring a notepad and pen next time and you won't end up with your dic* in your hand at the end of the night.
luv it!
May. 1, 2008 at 4:11 PM
Posted by Maria S.
This article is pure genius. It changed my life. In a good way. And I don't even live in Boston.
All the same?
May. 1, 2008 at 8:00 PM
Posted by Anonymous
Are all of the Cougar Hunters such jerks? If not, I may perch my little butt on an Abe & Louie's bar stool next Thursday evening.
Why Not?
May. 2, 2008 at 7:24 AM
Posted by Mike D
You guys are all awesome. "Anonymous" telling other anonymous people to stop being anonymous and fight at the gym. Great. Nice work. Too bad the only one who remains un-anonymous is poor little Matt, who I am sure thought he was doing a landmark interview, but instead might have realized his tactics and game are better left anonymous and untold. I think Boston Magazine is pathetic for printing this. Your magazine is now no different from the Improper, stuff @ night, www.dirtyscottsdale.com, etc. I thought you guys were a classy mag, not one to publish such smut. The editor should be fired.
Poor Taste by Magazine in General
May. 2, 2008 at 7:28 AM
Posted by Christina R
Mike D- I agree with you- I always thought that this magazine was a classy one- As a Miami resident and a person who comes to Boston every now and then, I used to think Boston Magazine was a good place to see what was happening, read interesting and VALUABLE (not trashy) articles about exemplary men and women who positively impact the community. Instead you (the editor and co.) have stooped to the level of tabloids and other magazines most would find in a housing project. So much for being "A Guide to the Good Life" as you call yourselves. I only looked this morning to see if there was more trash talk...oh well. Great entertainment yesterday though! Gracias, amigos! :-)
CANCELLING
May. 2, 2008 at 11:10 AM
Posted by Mike D
I am cancelling my subscription based on the fact that this magazine seems to have deteriorated to the point of this??? Most of our family friends are as well, as many don't feel comfortable allowing their young children to be exposed to this crap.
hey darling tough guys -SCLA-
May. 2, 2008 at 11:38 AM
Posted by d n
hay darlin mathew eugene,you and youre whole gang of anonymous tough guys seemed a little lets say not so tough when someone who must be involved walked up to you all on the floor at the SCLA last night. i guess you being so absolutely gorgeous but very fat, homeless, car less, jobless and have to sleep at your boyfriends house on a couch takes you off my potential list.im sad... i thought it would of been a great one night stand. miss you
WOW
May. 2, 2008 at 11:47 AM
Posted by Mike D
Matt move out of this city now. You're gig is over.
ha
May. 2, 2008 at 11:52 AM
Posted by matt rosa
I love the war I started!!!!
A fight at the scla...haha!!
May. 2, 2008 at 12:35 PM
Posted by Anonymous
What are you guys going to do, throw money at each other?? Maybe someone will be crazy and throw a credit card really hard??
Matt used to stalk me on AOL in high school
May. 2, 2008 at 11:58 AM
Posted by Anonymous
I Thought that perhaps you all may find it highly appealing that Matt Rosa, the supposedly "edgy" Boston based "Cougar Hunter", is from Upstate New York...spent highschool rolling deep with his "posse" of Cool Kidz who totally defined the word "cool" by thug walking around with "really badass and unique" Tribal Tattoos, rather large Doorknocker-hoop-earrings, and never without a Wifebeater clinging to their Big HeMan type Muscles. Matt Rosa & his "Boyyyyzzz" often spent time perusing America Online Profiles...circa 1997 when it first became quasi normal for everyone to have a dial up modem. Matt Rosa & Co. then would all huddle around someone's family computer & practice their social skills by IM-ing local 14 & 15 year old girls from neighboring schools and arranging to meet up with them at Albany's Finest: Crossgates Mall. Since Rosa was on a mission to become a future "Cougar Hunter", it was natural for Rosa & Crew to cruise around Albany in Style in their sweet ass rides...or "wh
hahah
May. 2, 2008 at 12:44 PM
Posted by matt rosa
hometown love!!! 11 years of pent up frustration!!! Unleash the fury mitch!!! Hey B.N. Miss you too!!!
This is getting absurd
May. 2, 2008 at 12:55 PM
Posted by Anonymous
Why give Matt such a hard time for simply revealing some things about his dating life? He's a single guy in a city who knows how to pickup women. Seems to me that some of you may be jealous.
WHAT!
May. 2, 2008 at 1:19 PM
Posted by Christina R
I would just like to add that as a woman, I find it not only a turn-off, but a sign of severe insecurity for someone to go public with things that should ultimately be held as private. I am sure that the poor women who unfortunately probably just felt bad for him and let him into their lives feel violated and probably angry. I think he should have just done it anonymously if you’re going to do it all. And Matt, I wouldn’t count on a TV show unless you drop at least 60 pounds and start all over. Translation- no chance in hell.
From Tool Bag to Designer Tool Belt
May. 2, 2008 at 1:27 PM
Posted by Stalked By Matt Rosa in Highschool
hahaha, Matt Rosa, the young lad who started his hunting skills as the infamous "AOL TRAINING BRA HUNTER" How are your nipple rings and tribal tats doing from Myrtle Beach Spring Break 1998?, the Armpit of the East Coast
Get back to work
May. 2, 2008 at 1:34 PM
Posted by Anonymous
For some of you who are so offended by this article, you are certainly wasting a great deal of your time keeping up on the message boards and putting in your two cents. Some of you don't even live in Boston????
RE: Get Back To Work
May. 2, 2008 at 1:35 PM
Posted by Your Mom
We're not so much offended by the article as we are of Boston Magazine's Glorification of a social climbing, womanizing lazy ass paralegal pink lady tool kit named Matt Rosa. The truth just needs to be relayed, thats all. O'Doyle Rules Losah!
I Suck
May. 2, 2008 at 1:45 PM
Posted by Anonymous
I admit it, I am a loser. I need a job!
WASTE
May. 2, 2008 at 2:00 PM
Posted by Christina R
No, its not wasting any of my time. You obviously keep checking back in to see what we wrote. In fact, I would love to see this magazine spiral further into trashiness. The editor can have the legacy of "The Editor that saw Boston Magazine turn into the best Boston Tabloid." I used to go online and read alot of good stuff on this site because I love Boston but now a magazine catered to the high class decides its going to glorify the using of women and make a total joke of more serious issues such as adultery and unemployment.
Matt Rosa
May. 2, 2008 at 2:09 PM
Posted by Anonymous
This kid sounds like such a loser. Does anyone know if that is really him writing on this comments section? If it is, you suck. I thought only chicks and people who are too stupid to get into law school were paralegals? I'll bet all of MY money you used to sell mortgages too.
Reply
May. 2, 2008 at 2:31 PM
Posted by Anonymous
And posting a sexist comment like that makes you a bigger person?
Paralegal
May. 2, 2008 at 2:30 PM
Posted by Anonymous
I was being sarcastic, relax. But how many male paralegal's do you know?
Huh?
May. 2, 2008 at 2:44 PM
Posted by Anonymous
Dear Boston Magazine, My "crew" and I are in our early thirties, good looking, wealthy and like to hang out with young, attractive women. Does that make us cool?I don't know whats more pathetic, washed up old women hanging out at bars or losers like this kid Matt who are proud of the fact that they have zero ambition in life. Gee, I really hope I can go out tonight,meet some divorcee and hopefully have her buy me an iphone! Let me know if you need a loan sucka.
HIGH STAKES???
May. 2, 2008 at 3:10 PM
Posted by Mike D
Wait a second. I just remembered something. This alleged "paralegal" has time for midday sex, spends all his time at the gym, is homeless apparently, needs people to buy him things, yet loves to play "high stakes poker games?" Am I the only one who noticed that? If I didn't spend most of the day stuck in an airport I don't think I would have. Just thought it was sort of odd.
Me
May. 2, 2008 at 3:33 PM
Posted by Matt Rosa
Move over Bill Buckner, I just became Boston's most hated man!!!
Disgust
May. 5, 2008 at 7:41 AM
Posted by Anonymous
Matt isn't even attractive AND he has no job!! He lives off of other women...he's pathetic and overweight!
assumes
May. 5, 2008 at 3:45 PM
Posted by chuck allen
that most if not all guys would want ot be able to do what he does and have his life . AHHH not really Matt , but i guess every parents best case scenario for thier kids is the ability to pick up women and sometimes profit from it , great work you life is surely many envy .
gigolo
May. 5, 2008 at 4:00 PM
Posted by chuck allen
i bet Matt's mother appreciates it when she gets questions about what Matt's " UP TO ", in Boston , yeah how's your devoted loving son Matty doing ?/ well errrr ahhhh he's in Boston , ahhhh ummmmm , he's working " I THINK ", WHAT IS HE DOING ?? ERRRR AHHHHH i think something in sales . whats he selling ?? errrrr ahhhhhhh Im not sure really but he "TRAVELS AROUND A LOT ", well thats pretty truthful i guess , he does travel { from bar to bar } and he does sell something { himself i suppose } and mkaes somewhat of a living { not really }. he'll be the same guy in 10 years at CLarke's HITTING ON 24 YEAR OLD'S . Who said you can't "GO HOME AGAIN ", and come full circle . it's his life and if he thinks this is what he should be doing with it , it's sad but it is HIS LIFE. good luck to you MATT , I HAVE A FEELING AT SOME POINT YOUR GOING REALLY NEED IT .
Matt Rosa the looser
May. 5, 2008 at 4:59 PM
Posted by Anonymous
This guy is the biggest looser in Boston actually can't get chicks he just lies about it, is addicted to drugs, is homeless and I have heard is terrible in the sack... as for his alleged job as a paralegal that one's made up too.. If I were an older woman I would at least want a good looking guy!
ha!!!
May. 5, 2008 at 5:05 PM
Posted by matt rosa
Looser? Classic....this gives me more stuff to talk about on Matty in the morning next Tuesday......
Trash
May. 5, 2008 at 5:15 PM
Posted by mathias spelt
I am disappointed in Boston magazine. This is such trash and poor reporting. It is shameless. I am cancelling my subscription.
Women are not fools...
May. 5, 2008 at 10:06 PM
Posted by Anonymous
Everyone on here seems to think these women aka Cougars are idiots. Women, especially experienced ones, don't need someone else to look out for them. They know exactly what they are getting into. Just like wealthy sometimes good-looking older men don't need anyone to defend them about young girls preying on them either. The comments are ridiculous and some have nothing to do with anything. Grow up and do something valuable with your time. Not to mention unless you can speak from experience about sleeping with Matt you cannot say he is bad in bed...which he most certainly is not...
kudos
May. 6, 2008 at 10:48 AM
Posted by sexy lexy
i think what matty is doing is commendable it’s hard not to be jealous of someone who has found a way to so cleverly bypass pushing paper around in a cubicle all day women have been using older dudes for their money all along…what’s so wrong with a guy doing it?
rosa
May. 6, 2008 at 3:03 PM
Posted by jc jc
I don't think this is the rosa from upstate cuz he had a serious gf in college. If it is, who cares, older men date younger women all the time and no one cares.
fabrications
May. 6, 2008 at 4:00 PM
Posted by Anonymous
Knowing some of the people involved this is an article based on pure fabrication and lies. Matt doesn't really get women to pay for things, he actually steals from them and lies about it. He is lucky not to be in jail and is getting way to much attention for making up stories.
haha
May. 6, 2008 at 4:28 PM
Posted by matt rosa
Classic again, I guess I AM LUCKY.....ha , Ill be sure to mention all of this on the Opie and Anthony show this thursday at 915am!!!! Dont be afraid to call in with all your "true" stories ..........
Moron
May. 7, 2008 at 8:09 AM
Posted by Anonymous
O&A Show ends at 9am in Boston dickhead.
clever
May. 7, 2008 at 2:10 PM
Posted by matthew rosa
well since someone finally figured out how to emulate me I will spread the truth now..anyone who knows my life knows that certainly isnt where I live also anyone who would like to call me fat to my face is more the welcome to say something to my face at the sports club..another thing the two women in this article are nothing but great girls and are probably two of the best looking women I've ever seen so all you jealous punks should probably use you energy trying to figure out why you are spending most of your time responding to an article that has nothing to do with you because my thoughts are that you just feel a tad bit insecure with your manhood if you know what I mean.....p.s.nice try on calling out the wrong address punk...I know who you are
fan club
May. 7, 2008 at 9:57 PM
Posted by Anonymous
matt rosa.....i go to to scla and had to find out who you were for kicks. my friend pointed you out and i cannot get over how admiringly gorgeous you are. i can only admire you from afar becaue i am a cougar, but not of your calibur. keep preying, matt, we women love it, even if you think we don't know what you're doing. WE are the smart predators. smarter than you'll be for years, however, i applaud your grace. keep it up. and all you people shitting on him...........go to bed. he's more clever then you'll ever be.
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