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The Dos and Don’ts of Dating Older Women

The Dos and Don’ts of Dating Older Women:

It occurred to me the other day that the 27-year-old man I’m banging is TEN YEARS YOUNGER THAN ME, and, holy shit, I’m officially an “older woman.” I’ve dated younger men for decades. In fact, I married a guy four years younger. It takes a special kind of guy to hold onto a woman of experience. I’m here to help you avoid making rookie mistakes. Although, on the other hand, we’re kind of expecting you to make them. It’s adorable.


DON’TS

CALL HER ‘OLDER’
Or qualify your compliments by saying things like, “You look amazing for your age.” Just say, “You look amazing.”

MAKE HER YOUR FETISH
She’s not a foot or someone whose car won’t start (yes, that’s a thing). While chatting up some 20-somethings on Bumble I heard “I always wanted to be with an older woman” at least three times. Thanks to PornHub analytics we know dudes are way into the MILF and stepmom genres. Don’t use us to work out your Oedipus Complex.

INTERROGATE HER
You’re curious about our very long life. We get it. But don’t ask her how many people she’s slept with. That’s a question only a 19-year-old asks, and also she probably has no idea. She stopped counting right about the time you started wanting to date older women.

PLAY GAMES
As Jodi Miller, comic and proud cougar, says, “We can get that from guys our own age. Be straightforward.” Older women know what they want and don’t want. They know what they’re willing to put up with (and what they won’t) for a roll in the hay. If you’re going to flake because you want to bang that 23-year-old you’ve been chasing, just tell her. She’s a big girl, and you have no reason to lie.

SEND UNSOLICITED DICK PICS
This is literally on every list of “Don’ts” for men. JUST DON’T DO IT. NO MATTER WHAT THE AGE.

ASSUME SHE’S GOING TO BE YOUR MOMMY
If you want someone to do your laundry and clean, hire a cleaning person. If you need someone to tell you how perfect you are—older women are not for you. We are going to give it to you straight. The flipside: don’t assume if she has a kid she’s looking for you to be their daddy.

ASSUME SHE’S DESPERATE
Especially to get married or have a kid if she doesn’t have one. If that’s something she’s serious about, trust me, she isn’t auditioning young dudes to fill that role. However, and this is very important, if you start getting serious with a woman over 30 and you have no intention of impregnating her anytime soon and she’s told you that she wants kids, DO THE RIGHT THING AND GET OUT. Don’t you dare steal precious childbearing years from her just because the sex is amazing and she makes a solid omelet.

BE JUDGMENTAL
Or intimidated by her sexual prowess. Older women are like war vets—we’ve seen some shit. We’ve been the other woman. We’ve been the second woman in an open marriage. We’ve had threesomes and foursomes and been to sex dungeons. Just roll with it and soak up the knowledge. (P.S. Don’t judge any woman at any age for this.)

MENTION HER SCARS
For that matter, it’s best never to ask a woman about her tattoos unless you want a story of tragedy or regret or how a Marilyn Monroe Pinterest quote inspired her to take charge of her sexuality. My friend Coco is a creative, recently divorced mother of two, and she said, “Be aware that an older woman might have scars like a c-section scar or breast implants scars. Not all scars look alike. Do not mention anything about her scars except that you dig them. Not mentioning anything until she brings it up with you is always the best bet.”

TWEET YOUR TINDER ACTIVITY
I’m guessing you don’t do this anyway if you’re a stand-up guy, which I’m assuming you are, and not sketchy like me (which you should assume all older women are), but out of respect for the multiple people you’re juggling, keep that shit on the DL. Friend Diana Dinerman said it best: “Dude, I know we’re cas, but I don’t need to read about it.”

BE SELFISH
In bed. With money. At all. If an older woman even so much as senses that you’re more concerned with your needs than hers, kiss that ass goodbye.


DOS

SPARE HER THE BS
She can see it coming a mile away. Just be real. Anything else and she’ll cut you off faster than you can say, “I bagged a hot cougar.”

EXPECT HER TO BE BUSY
If you want someone who’s constantly wondering what you’re doing and is at your beck and call, dating an older woman probably isn’t for you. A wise woman knows that men come and go, but you only have so much time to focus on your career. Sure, some men are unicorns, and they’re worth sacrificing precious work time for. But older women often are at the point in their lives when the boycraziness takes a backseat.

BRING YOUR A-GAME
She’s going to expect foreplay. Not just expect. Demand. I was recently making out with a younger dude, and he had the condom on and was ready to go after we kissed for like two seconds. I said, “Um you think we’re going to have sex? You haven’t even touched my pussy.” He said he wasn’t into that, to which I said, “Get the fuck outta here.” If I want boring sex that lasts four minutes I would’ve married an old rich guy I wasn’t that into. That shit better be OFF THE FUCKING CHAIN. I better be bragging about you to my girlfriends over brunch or what are we even doing?

FUCK HER BRAINS OUT
Should go without saying, but I’m saying it. Your muscles should be sore. She should have to stretch before and after. The bed should end up in the middle of the room. She should be composing odes to your cock. You should be a legend thousands of years from now, a story passed down through generations of the Cougar Clan.

COMPLIMENT HER
If she sends you a hot video, don’t just respond, “Hot.” I cover a lot of this in my Guide to Sexting Etiquette. But for God’s sake. Make a fucking effort. And again, stay away from backhanded compliments that reference her age like, “You sure have great taste in hip-hop for someone from The Greatest Generation.”

COMMUNICATE FREQUENTLY AND THOUGHTFULLY
Show her the courtesy/respect of returning texts and phone calls in a timely manner. (You should do this with women of any age.) Let her know you’re thinking about her occasionally. I’m old. If you aren’t constantly reminding me you exist, my vagina gets Alzheimer’s and starts wandering around the neighborhood looking for a new friend.

LISTEN TO HER
Again, this is a good rule of thumb in general with women and—hell—with humans. But if she’s telling you she does or doesn’t like something—take it in. Women over 30 have figured themselves out. She’s not telling you that story about her bonehead ex to hear herself talk—she’s warning you.

APOLOGIZE
Don’t always try to win the argument. We tend to care more about coming to a place of compromise than winning the argument. Follow suit.

BE A GENTLEMAN
Bring adult surprises like wine or flowers; lingerie is always fun. Open doors. Make dinner reservations. We like things old-school.

BE YOURSELF
My friend Coco said, “Don’t try to be more mature than you are or be anything other than who you are.” I don’t need you to pretend to read The Economist or like the symphony. A woman of experience knows what she’s getting into with a younger man. Just don’t act shocked when we have no idea which album Drake just dropped or lack Snapchat skills.

CLEAN YOUR BATHROOM
If only to get rid of the beard scraps that appear like pubes on your sink. Again, from my friend Diana Dinerman: “Small things are not deal-breakers for me. But please consider the optics. Attraction is a 360 experience.”

ASK US WHAT WE WANT
Comic Jodi Miller put it best: “They should feel free to say things like, ‘Show me what you want me to do’ in the bedroom if they don’t already know. Then again, I’m hoping they already know.” If you don’t already know, we look forward to telling you.

BE GRATEFUL
The biggest mistake young men make is acting like lazy, entitled princes the minute they get a taste of the pussy. If you spend time in any woman’s house or bed or vagina, be a decent guy and thank her THAT DAY for the time you spent together. A thank you text doesn’t mean you’re getting married. It just means that you appreciate that she shared her body, her mind and her coffee with you.

BE READY FOR HER TO BLOW YOU AWAY IN THE SACK
They say a woman’s sexual peak is in her 30s, and from my experience and conversations with other women this peak doesn’t end until sometime in her 50s. She’s going to teach you things. An older woman is in touch with her body, her sexuality and her g-spot. Be prepared for explosive, multiple-orgasm, kinky sex.

LEARN FROM HER WISDOM
We have a lot of life experience to offer and many a young man I spoke with told me the older women they dated were instrumental in making them better all-around men. Better lovers. Better boyfriends. Better dressers.

KNOW YOUR PLACE
Understand you’re likely a placeholder, a rebound or a hot distraction. That doesn’t mean she views you as a piece of meat (although she might), but more than likely she’s not expecting you to fill her emotional needs or be a provider. She’s just looking for good orgasms. That being said, never rule out love. Love is the wild card. Love can strike anyone at any time, so…

STAY OPEN-MINDED
To sex stuff. To butt stuff. To love. At 26 I was banging a man five years younger than me with the full intention of making him the best summer fling ever. We ended up married. Don’t put too many parameters on the relationship, and don’t constantly bring up the age difference. Just let it all be whatever it wants to be in order for you both to get the most out of the experience.


Bridget Phetasy is a writer and comic in Los Angeles. Twitter: @BridgetPhetasy.

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