Art by Daiana Feuer


Photo by Art by Daiana Feuer

Hollywood’s Guide to Age-Inappropriate Dating

Tips for finding your own May-December relationship from Tinseltown’s finest.

Michael Douglas, 69, and Catherine Zeta-Jones, 44, just separated. Clint Eastwood and his wife (age difference: 35 years) have split. Soon, these seniors will be on the prowl once again for younger companions—because the closer you are to impending mortality, the more essential it is to stave it off with a PYT. And flaunting a much younger lover isn’t just for men anymore. For advice on bagging an older paramour, look no further than to Hollywood—where the worst thing you can possibly act, is your age.

Tip #1: Be a yoga instructor.

Flexibility is synonymous with sensuality, so maybe that’s why Alex Baldwin snagged himself a yoga instructor in wife Hilaria, who’s now 29. But the most successful Baldwin bro is also practical: He knows his anger-management issues can raise his blood pressure, which could shorten his lifespan. Can this Zen goddess help him namaste his way to eternal youth? Stay tuned.


Tip #2: Be a backup dancer.

Smooth-chested man-boys with foreign-sounding names caught Madonna and JLo’s eyes. These back-up dancers, aged 25 and 26, sealed the deals by ostensibly telling their girlfriends how fine they look from behind.


Tip #3: Teach ’em how to use technology.

Sir Patrick Stewart’s 35-year-old wife is a YouTube aficionado. And thanks to her, he’s stayed relevant in the digital age by also futzing around on Vine and Twitter. In fact, @SirPatStew has gotten so savvy that he even announced their marriage through the latter—with one of the goofiest wedding pictures of all time.


Tip #4: Get pregnant!

As Kelsey Grammer’s 32-year-old wife discovered, there’s no better way to make him feel forever young than by letting him fertilize you with his powerful seed. Bonus for you: As long as you’re pregnant, you can avoid having sex with him.


Tip #5: Catch her on the rebound.

After being married to Sean Penn, wouldn’t you want to be with…the opposite of Sean Penn? Perhaps what attracted Robin Wright to boy-toy Ben Foster (17 years her junior) was his sweet and mellow demeanor, born of the fact that he comes from a new generation of more sensitive male actors. Also—and this is key—he’s not Sean Penn.


Tip #6: Play a low-impact sport.

Where would Susan Sarandon meet 36-year-old beau, Jonathan Bricklin? At the ping-pong table, of course! And if there’s any woman who could make ping pong as flirty as couple’s tennis, you bet it’s Susan Sarandon.

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