Navigation

Vice City Pillow Talk: Where the Cougars Are

Mid- to late-twentysomething guys can be gateway drugs to getting back into dating and relationships.
Image: Older woman on the back of a younger man
Are you an older woman thinking of dating a younger man? Have fun, but keep it casual. Photo by Troy Aossey/Getty Images
Share this:
Carbonatix Pre-Player Loader

Audio By Carbonatix

I was creeping toward 40 when I got divorced and emerged, shaky and disoriented, back onto the dating scene. Since then, one very specific type of male has typically approached me in public: 26-year-olds. In the beginning, this confounded me. I'd never considered younger men attractive or datable, and I was just as confused about why they were interested in me.

It turned out I wasn't alone. All the middle-aged, newly divorced women I knew were experiencing the same phenomenon, and most of them were already dipping their toes into the baby-man pool. In other words, the cougar life chose us. Mid- to late-twentysomething bros essentially became gateway drugs for us back into dating and relationships. They provided much-needed levity after sometimes long and gut-wrenching separations, and we welcomed them — along with our revenge bodies and good credit — with open arms.

Like many of us, I'd been programmed to believe that a woman's sexual desirability diminishes in step with her fertility. A man's, by contrast, seemed only to grow with every distinguished line, a patch of gray, and contribution to his 401(k). There may be shreds of truth there, but, for the most part, it's antiquated thinking.

So what's changed? In short, the game. Many men are seeking out sexually experienced, mature women who know what they want. That doesn't always come with age, but it sure makes it easier. And no offense to the Golden Girls, but ladies in their 40s and 50s look different these days, especially in Miami. Have you seen Jennifer Lopez? At 55, she arguably looks better than she did as a 28-year-old playing Selena.

Sex appeal is part of it, but so is convenience. In an era of serial situationships, there is usually a temporary nature to older women/younger men pairings. For women who have checked off most of their life-stage boxes, a long-term partnership isn't necessary, leaving room for fun. For men, there can be a thrill to the almost subversive nature of a Stiffler's-mom experience.

It's not all fun and games, though. Here's the thing that no one tells before joining the cougar life — being with a younger man is a lot of work. Real or imagined, the pressure to stay youthful, physically and mentally, for your lover can require more effort than it's worth. As one friend, a reformed cougar, told me, "It just got fucking exhausting." She's now happily dating a man her age and spends much less time plucking gray hairs in front of the mirror.

As women, many of us already put an exorbitant amount of effort into our appearances. Add a younger man to the equation, and it can quickly go off the rails. Yes, that sounds incredibly shallow, but it's also honest. As evolved as we are and as confident as we can be, the pressure for perfection, or something close, is real. If you are a woman of any age immune to this, then you are clearly God's favorite.

My cougar era has been well documented, though it hasn't followed conventional wisdom. Those who came before me warned me to keep my experiences brief, fun, and casual. Did I listen to them? I did not. Twelve months later, I am still tucking Z in for bed at 9 p.m. so he can make the gym by 6 in the morning. (Fact check: He's only seven years younger than me.)

Does age matter? Sometimes. Things like life stage and maturity are more important, so it isn't unheard of for cougar relationships to last the test of time. Some of the world's sexiest couples are long-term older woman/younger man pairings. Just look at Chris Hemsworth and Elsa Pataky, Ryan Gosling and Eva Mendes, or Nick Jonas and Priyanka Chopra. If it works for Thor, who are we to judge? So here's to you, Mrs. Robinson. May the rise of the cougar ascend forever and ever.

Where to Spot a Cougar in Miami

Barry's Bootcamp

Various locations
barrys.com
According to owner Derek DeGrazio, the cougars here are often mistaken for pumas (younger women). Find us in the red room sometime after 9 a.m., usually starting on the treadmill. You can make subtle eye contact with the mirror; just don't break our flow.

The Living Room at Faena Miami Beach

3201 Collins Ave., Miami Beach
faena.com
I've previously listed this as a great place to meet sugar daddies/babies, but really, it's a fabulous breeding ground for all the age-gap relationships, especially if you're looking for someone to float the bill.

Casa Tua

1700 James Ave., Miami Beach
casatualife.com
We'll be upstairs on Wednesday singing karaoke. You'll get extra points if you buy us a spicy skinny margarita.

Trader Joe's

Various locations
traderjoes.com
Our kids require a lot of snacks. Just, please, do not approach us while the little ones are present.

Anywhere That Offers Microneedling Facials

Boosting our collagen levels is a full-time job. Look for us under our giant visors and a thick layer of SPF 50. Tell us our skin looks amazing.

Pillow Talk to Me

I want to hear from you, Miami. Send me all your dating wins and losses for a chance to be featured — anonymously or not — in this column at [email protected].