We think every man should have a fling with an older woman at some point in his life. Cougars have skills to share, and they like no-strings relationships. Here’s how to get started.

Master The Art of Being Cougar Bait

Guys who have dated and/or slept with a woman who’s significantly older know that with age comes experience — and that’s just one of the many benefits of bedding a cougar. There’s a confidence that comes with being a woman of a certain age that’s key to why the sexual relationship can be so beneficial to a young guy … and why so many men in their twenties and thirties are looking outside their peer group for partners.

Finding a cougar of your very own can take some work, but the rewards are definitely worth the effort. First, it’s important to understand that to qualify as a true “older woman,” your partner needs to be considerably older than you. We’re not talking a few years’ age difference. Generally, a woman ten or more years your senior (and over the age of 40) will provide the type of adventure we’re recommending.

Where To Meet Them

Sure, hot older women are all around: waiting in line at Whole Foods, having lunch at outdoor cafes, or browsing the sale rack at Neiman Marcus. But if a sexual relationship with a cougar is what you’re searching for, go straight to the den.

Focus on Upscale Lounges and Hotel Bars

Establishments that serve alcohol are your best bet, but your local dive bar isn’t going to be crawling with over-40 ladies looking to make sexy time with you. Eschew bars and pubs in favor of lounges. Grant, 28, met his current girlfriend, Daphne, 42, in a bar, but it wasn’t your typical watering hole. “I recommend somewhere a little more upscale if you’re trying to connect with a more mature woman, which I usually am,” Grant says.

“You’re probably not going to find a sexy, professional woman at a sports bar. My rule of thumb is that if the cocktails cost more than ten bucks, she probably has her shit together. This is the kind of woman I want to meet.”

“When I first approached Daphne,” Grant continues, “she was sitting at the bar by herself, drinking bourbon on the rocks. There’s something incredibly sexy about a woman who’s okay being alone and knows how to order a real drink.”

Hotel bars are always a good bet, but we’re not talking about the Holiday Inn. In New York City, the Pierre and the Gansevoort are worth checking out. A restaurant such as T-Bar on the Upper East Side is also reliable. In Los Angeles, hot divorcees and even hotter housewives can be found at the Ivy or the opulent Good Luck Bar, with its Asian-inspired decor.

No matter where you are, home in on the lounge of the town’s classiest hotel or scope out the bars at upscale restaurants for ladies who are enjoying a cocktail alone.

Hit the Gym

The gym is the perfect place to meet a hot older woman, since the fact that she’s there means she takes care of her body. “One of the hottest sexual experiences of my life was with an older woman,” says Andrew, 33. “It involved sex in the locker room of my gym. It was very much unplanned but extremely intense and uninhibited. I think that’s why I like dating an older woman so much — the lack of inhibition.”

“I met Morgan during one of my morning workouts,” Andrew continues. “She’s 48-15 years older than I am. Up until that point I’d only been with girls my own age or younger. But I noticed her right away. First of all, she’s in better shape than most of the women half her age on the machines next to her. But even better, she’s just comfortable in her own skin. Every time I saw her she gave me a big, friendly smile. Talking to her is easy. She’s just more sure of herself, and that’s very attractive.”

Go Back to School

Taking a continuing-education class or joining an organized recreational activity is another smart strategy for meeting your Mrs. Robinson. Recent divorcees and widows are likely to sign up for activities that allow them to explore new interests, or those old ones that took a back burner to kids and careers. Whether it’s an Asian cooking class, a wine-tasting seminar, or a coed book club, you’re likely to meet older women who are getting back into the dating game.

Pursuing your own interests-as long as those interests are something other than video games or extreme sports-can be another great way to meet cougars. Patrick, 30, is a musician who has never had trouble meeting women. “The guitar definitely ups my appeal with the ladies,” he says laughingly. When Carmella, 50, went to hear live music in a club where Patrick was playing, she approached him after the show. “It was refreshing, how forward she was,” he tells us. “I’m used to having to do the work, but she made her interest known right away by asking me for guitar lessons.” He describes their first lesson as more of a first date. “There were drinks, there was laughter, lots of chemistry. We started off on my couch and finished the night in my bed. She was very up front about what she wanted. There was no ‘three-date rule’ or pressure to commit. Which actually made me want to spend more time with her. The biggest turn-on was that she didn’t need me-she wanted me.”

The Cougar Pickup

You’re young, you’re in great shape, and you can rock a tailored suit like nobody’s business. Unfortunately, if you’re looking to snag a quality cougar, that might not be enough. While younger, wide-eyed girls let you get away with snarky jokes or cheesy pickup lines, an older woman requires something more. And while offering to buy her a drink is a solid opener, make sure you have a few meaty topics you can banter about. Talking about current events or the last book you read (when the moment is appropriate) shows that you can hold your own with someone who, at this point in her life, is keeping up with more than the Kardashians.

Even though the cougar may be intimidating-after all, she’s sexy, confident, and experienced — make sure you let her know you’re interested in her sexually. Flirt and inject a little innuendo into the conversation. Whatever you do, don’t mention your age difference or, even worse, her age. Maybe at some point in the future you two can joke about the fact that she’s old enough to be your mother, but at this point, the last thing you want to do is make her feel like she’s in the same category as the woman who sewed your name into your undies when you went to summer camp.

And while we’re on the topic of mothers, don’t compare her to yours. Even if they both happen to have the same designer handbag, drawing this comparison is a surefire way to send your cougar into the arms of a smarter cub. Remember, the thrill of.being with you is that she gets to experience your youth and vitality. Don’t make her feel like you’re thinking about her age.

Finally, keep in mind that when trying to catch a cougar, your thinking needs to reflect the old adage, You have to spend money to make money. Even if she’s a potential sugar mama, you still can’t expect her to do all the wooing. Buy her a drink, pay for her dinner, splurge on flowers, and chances are you’ll secure your spot in her thoughts and fantasies.

As more fit and attractive women re-enter the dating pool, your chances of success with an older woman are high. If you’re intrigued by the possibilities a relationship-or hookup-can offer, go for it. Enjoy the fact that she knows what she wants out of life, and that she is financially independent. As a younger guy, you can match her sensuality with your sexual energy, creating a union that is extremely hot.

The Benefits of Cougars

  1. There’s plenty to love about dating a cougar, including the fact that they can be easier to connect with. Unlike their younger counterparts, they don’t travel in packs. “Girls my age have to do everything together, including going to the bathroom,” says Grant. This means it’s much easier to strike up a conversation with an older woman, and that you can still look for a hookup when you don’t have a wingman.
  2. Blissfully absent from these flings and affairs are “where is this relationship going” conversations. Since your potential cougar has probably already had the husband and kids (if she wanted them), she’s more likely to enjoy the relationship without feeling the need to put a label on it.
  3. When a woman has 20-plus years’ experience between the sheets, chances are she’s better in bed than your average coed. She’s had time to perfect her technique. “The first time Daphne went down on me, it was like a whole other level of orgasm,” says Grant. “She did things with her hands and mouth-it was just masterful. But the best part was that she looked at me the whole time. I can tell she enjoys doing it, whereas with my previous, younger girlfriend, it always felt like she was doing me a favor. Daphne says that around the time she turned 40, she lost her inhibitions and really started to enjoy sex.”
  4. Patrick finds that sleeping with a more mature woman like 50-year- old Carmella means fewer hang-ups. “When we’re together, we spend most of our time completely naked,” he says. “Carmella has long dark hair, a petite hourglass figure, and the most perfect tits and ass I’ve ever had my hands on. If she has any flaws I don’t notice, because she isn’t constantly assessing herself in the way that younger girls do.”
  5. An older woman is more likely to be in touch with her body and what gives her pleasure. “There’s no other way to say this except that she is an expert at making herself come,” says Andrew about Morgan. “With other partners, I could spend a good 30 to 40 minutes and still feel like I was pushing all the wrong buttons. Part of being good in bed means knowing what you like, and Morgan’s not shy about expressing that and showing me how to make it happen.”
  6. An older woman, especially a divorcee, can be really into a sexual relationship. “I don’t know how to say this without sounding arrogant, but in a way, she’s more grateful,” says Grant. “After being married for 18 years, I think Daphne thought this chapter of her life was closed, that all the hot sex was behind her. And now here’s this young guy, literally, behind her.”

The Cougar Downside

  1. Even though celebs like Halle Berry, Demi Moore, and Madonna have brought older woman/younger man relationships into the mainstream, there’s still a certain stigma attached to these pairings. But that doesn’t have to be a bad thing. In fact, what made sex with Morgan so memorable for Andrew was the thrill of doing something taboo. “People knew about our relationship, our friends used to tease us, and when I would kiss her or grab her ass, people at our gym would do double-takes. It was pretty hot, the feeling that we were doing something ‘wrong,’ or at least not socially acceptable.”
  2. There can be awkwardness around friends. “You can bridge the gap between your friend groups, but it’s tricky,” says Andrew. “I never want to put Morgan in a situation where she feels like the mom to a group of kids. That doesn’t mean we can’t socialize and have fun. It’s all about context. I’m okay with being in a group of her friends, knowing they’re calling me her ‘boy toy,’ but I wouldn’t expect her to go on a weekend camping trip with my friends from college and their twenty-something girlfriends.”
  3. A cougar may want to take the lead. But while you and she may never be on equal footing, there are ways to deal. Patrick tells us, “She may have more life experience than me, more money than me, even more insights, but at the end of the day, she still wants to feel like I’m the man.” Pay for her dinner, even if that means going to a cheaper spot. Show her how to do the things that you’re good at. Remember that even successful women want to feel taken care of. And don’t let her be on top in the bedroom all the time.
  4. No matter how much you like, or even love, your cougar, if you’re looking to have kids, you’ll have to look elsewhere. “We’ve talked about it, and Daphne understands that I want to get married and have a family someday,” says Grant. “We’re all about enjoying each other’s company, enjoying the moment.”

Dos And Don’ts with Cougars

Now that you’ve captured the attention of an attractive older woman, there are a few things to keep in mind.

  1. Do be up front about the relationship.
    Are you both looking for fun sex, sex with dating, or a long-term arrangement? Find out where she stands so that there’s no confusion as to the role you’ll play in her life.
  2. Don’t forget to ask about her current relationship status.
    It’s possible that she’s married and looking for something on the side. If that’s the case, remember that dating a married cougar comes with its own set of complications. Do you get the impression that her husband is okay with his wife being “entertained,” or would the guy come after you with a nine iron if he discovered you were doing his very doable spouse?
  3. Do talk about the age difference.
    This is best done once you’ve known each other for a while, and definitely not on the first date. “I recommend acknowledging the elephant in the room,” says Andrew. “Yes, there’s an age difference. Instead of worrying about it, we joke about it. She asks me if I need her to check my homework; I tell her she looks sexy in her reading glasses. I’ve found that a little humor can go a long way.”
  4. Don’t poach your parents’ peer group for dates.
    “Don’t dip into your mom’s book club,” says Grant. “I learned that the hard way. One of my mom’s good friends was always very flirty with me. I ended up asking her out for a drink, one thing led to another, and we slept together. It was a one-time thing, but my mother found out and things were very strained all around. Although I have to say that there was something very sexy about seeing Mrs. G., who once served me milk and cookies at her kitchen table, sitting on top of me. But no, definitely don’t do it. For your mom’s sake.”

We should probably mention that a person’s age — women in this case, but whatever, so long as they have passed the legal age of consent — has very little to do with their desirability. It may have something to do with how freely they express their sexuality, but that has more to do with life experience than some date on a calendar. … In theory you could rely on science to tell you about sexual peak and thus how to define Cougar in your mind, but at the risk of sounding like some silly Boomer, you’ll find that you can have good sex with someone you just met, but if you want to have great sex, you’ll need to share more with your partner than just what you look like naked. At that point your ages won’t really matter.

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