Sex + Dating

What I Learned From Dating a Much Older Man

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Some sexual fantasies are better left unfulfilled. Take threesomes, for example: fun in theory, but not so much when the wrong group makes things a ménage à disaster.

That was my experience from dating a much older man. What began as a romantic adventure into unconventional love turned into a disaster I should have seen coming from waaaay over the hill. Here’s what I learned from it all.

Age really is just a number

How old you actually are doesn't necessarily have a lot to do with your lifestyle. Even though this guy and I were 25 years apart, we had a lot in common. We worked in the same profession, had similar interests, and shared common philosophical views. I grew up the only child of older parents (who are also 10 years apart), and often felt like an awkward old lady trapped inside a teeny-bopper’s body. He was someone pushing 50 but didn’t act like it. We got along swimmingly… in the beginning. I didn't know then that our age gap would define the relationship.

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Old can be sexy

Age comes with wisdom. This guy was confident, successful, and comfortable with himself: a significant departure from the insecure, possessive 20-somethings I had dated.

So what if he was wrinkly, in all the places you might expect? I admit, I wasn’t as physically attracted to him as I had been to other partners. But our chemistry was everything. Have you ever seen a girl with a hideous boyfriend and thought, “Seriously, how the f$*k did he pull that off?” Let me tell you. Either he's just a nice friggin’ dude; or being with him boosts her self-confidence.

I was a fantasy for my older man... which was an aphrodisiac for me. There was zero jealousy on both sides, and I never saw him check out another woman -- due to him being satisfied, of course, but also him being well-seasoned in how to respect the opposite sex.

Timing is everything

The Olsen twins both have boyfriends 20 years their senior. If Mary Kate or Ashley was approachable and not icy fashion prodigies, I would love to ask how they make it work.

In my case, the age gap was actually a cavernous black hole defying space and time. He didn’t want to get married (again). I knew I eventually wanted a family. He didn’t want to be raising a kid at 60. I got that; but even though I knew there was no future, I didn’t cut it off completely. I still liked the guy.

Eventually, it did fizzle out. Instead of just getting a hit of Botox, he was set on partying to prove it to himself and everybody else. A 50-year-old playing 30 grew past its prime for me.

It’ll age you

After it ended, he talked to a lot of people about our relationship -- and what happened through the grapevine was unexpected. Another lesson in dating: a fling with someone in your professional/personal circle is more often than not bad news. Older guys instantly thought they had a shot. Some guys my age made fun of me. Women judged me as having an ulterior, economic motive: “She just dated him for his money,” or “She thought she could get ahead.” In our society people are so quick to judge a young, naïve woman -- never the older man who perhaps should’ve known better too.

After all that, I got a few of wrinkles of my own.

The long haul: the older person gets even older

I have a friend who’s been married to someone for more than a decade who is 20 years older than her. He’s old and sick now, and she takes care of him (even financially), but she’s still partying and sleeping around. Obviously, he doesn’t know. I sometimes imagine what would have happened if I had stayed with my older man.

The last I heard, my older ex was in a tumultuous relationship with another 20-something, this time a singer reminiscent of Björk. As for me? I’m with a man eight years older than me. Twenty years was too many. The same age always seemed too young. But this guy feels just right.Sign up here for our daily Thrillist email, and get your fix of the best in food/drink/fun.

Sophia Glass is a San Francisco writer who now uses anti-wrinkle cream and avoids drama.

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