Older Women With Younger Guys: Secret to Successful Relationships?

Younger men

I got the most backhanded compliment the other day. Standing outside at the subway station, a tall, lanky kid — and I do mean kid — sauntered past, sized me up from my flip-flops to my wild hairdo, and broke out in a smile.

“Hey sweetheart,” he oozed. “What’s your name?”

My first reaction was to tell him to toddle along because I was probably his mama’s age but instead I watered my reply down to just “Ms. Too Old For You.”

He asked how old. I told him. His jaw dropped and his eyes got wide. “I knew you were a little older than me,” he confessed. “But I didn’t know you were that old.”

Oof. Pow. Bam. Talk about an upper cut to the gut. But it was funny and I had to laugh. Still, I have no idea how Demi and Mariah do it. I could never date a younger guy. More power to them for taking on the equivalent of a little brother or, even worse, another kid. 


Because I gotta tell ya, neither Ashton Kutcher nor Nick Cannon make good cases for the mannish maturity of an underage dude. (Underage meaning not less than 21. Underage just meaning under the ages of their respective wives.) They’re both cutie pies but man, they seem like a lot of extra work.  

Not that dating guys in any age bracket is a cakewalk. Men — old ones, tall ones, big ones, bald ones, dudes from the South, guys who sing on Broadway, sailors, psychotherapists, overpaid athletes, former governors from California with penchants for domestic help — they all come with their own sets of issues.

But far as I’m concerned, keeping company with a younger dude is like making it out of the labyrinth in one piece, then going back to do something stupid like take a picture or chisel a piece of rock from the wall as a keepsake. Nope. I say do not pass go, eyes straight ahead, to the safe familiarity of guys five years my senior or less. (I raise a cautious eyebrow at dudes who are a lot older too, but that’s another list of reasons and another post for another day.)

I mean, c’mon: after I’ve bested the rocky terrain of my early 20s and unsuccessfully dated fellas my age back then, why in the heck would I want to backtrack to be with anyone that age now?

When I was 23, my boyfriend at the time behaved like he was still fresh out of high school. That dude was just a little over a year older than me, but he was a sneaker and video game addict. I mean, every paycheck was a new pair of Jordans or Adidas shelltoes or PlayStation something-or-other. Interestingly enough, that’s exactly how my boyfriend in the 10th grade used to spend his money too.

And between sneakers, video games, bawdy humor, and rowdy sports, most other guys’ hobbies and interests haven’t changed much from the time we were kids, either. They just don’t mature as quickly as we do, so backpeddling in age seems like a set-up to make me old and withered before my time (especially compared to the fine, fresh-faced young thang I’m coddling by my side).

Before a fellow Stir-ette with a 22-year-old fiancé gets her britches all in a bundle, let me be clear: I don’t begrudge anybody their happiness. And if that beau comes wrapped in a little barely legal package, if their romance bloomed with someone who was just learning their ABC’s when they were prepping for their SAT’s, if they’ve written a love story with a guy who’s just a few years removed from reading fairy tales, all hail the gal willing to give it a shot.

I’m actually happy that Demi and Ashton and Nick and Mariah are doing well because May-December romances where the December is the woman are usually doomed from the giddy up. Society puts so much more pressure on women to stay youthful — or pumped full of creams and collagens if they can’t do it naturally — that it’s nice to see their relationships defy odds. But as for me, myself, and my fuddy duddy I, dating a younger guy is a step backward into a minefield of familiar old headaches.

Does growing acceptance give older chicks more of a license to date younger guys? Would you ever date a younger man?

Image via lastnightsshoes/Flickr

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