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Posted on June 23, 2018 by Christine Crosby in dating, humor, midlife, PETER GERSTENZANG, romance 50+

Back On The Market: Difficulties Of Midlife Dating

Back On The Market: Difficulties Of Midlife Dating and One Man’s Epiphany About Looking for Love in Your 50s


Back in high school, dating was an easy and enjoyable experience. The only hard part was asking the girl out, which, admittedly, required as much planning and strategy as The Normandy Invasion.

In those days, I had a couple of ways to approach it. I’d either play it cool, like James Dean, and act so indifferent that she couldn’t resist. Or I’d go the comedy route. By that, I mean I was funny and charming and tossed out great one-liners. This worked well, too, so I didn’t have to resort to doing anything embarrassing like putting a squirting flower in my lapel or wearing clown shoes.

It was all good fun. I often took the young woman to a movie, followed by pizza and soda. The only downside came the next day when the junk food kicked in and my face broke out and looked like a relief map of the Carpathian Mountains. All in all, though, I remember it quite fondly.

Dating in Your 50s

Well, I’m in my 50s and dating once more. And it’s gotten complicated. Using high school experience again, it’s like finally mastering algebra, then suddenly having to figure out binary logarithms — I don’t understand the subject and I’m afraid I’m going to flunk.

 “I was simply hoping for a pleasant evening with an easygoing, middle-aged woman. Instead, I got Lindsay Lohan’s mother!”

The trouble is, women now come with something they didn’t have when I was younger: baggage. So much baggage, I’m surprised my first date didn’t show up at the bar accompanied by three bellboys. (Midlife men have plenty of baggage, too.)

Other People’s Problems

My first date, Karen, certainly tried to be friendly and chatty. But unlike the old days, Karen had grown-up problems. Her child support check was late — again. Her boss was so demanding and scary it sounded like she was personal assistant to Joseph Stalin. Plus, her teenage daughter hadn’t stopped seeing the “bum,” and Karen was stressed about that, too — which resulted in her drinking three martinis in one hour.

I tried to be understanding about Karen’s problems. But I was simply hoping for a pleasant evening with an easygoing, middle-aged woman. Instead, I got Lindsay Lohan’s mother! After another hour of complaining and more drinks, I decided to call it a night, before things got any scarier, out:  meaning a bar tab as big as the national deficit. Or having to drive Karen to The Betty Ford Center.

Rosemary, a single woman pushing 40, brought another set of challenges. We’d barely sat down at our restaurant table when she asked me how I felt about kids. Before I could answer, she compared her biological clock to Big Ben. Then, to top it off, Rosemary actually did an imitation of Big Ben. So started drinking heavily, which worked well. I not only got nicely numb, but also convinced Rosemary that I wasn’t good father material. Soon, we moved onto a less frightening topic than having kids: Vladimir Putin’s invasion of the Ukraine.

An Epiphany About Dating

My single female friends tell me they don’t have it any easier. In fact, one of my best pals, Patty, calls regularly with similarly sad stories. She tells me the men she dates usually do one of two delightful things when they go out: They either surreptitiously scope out younger women or furtively check their phones to see who’s texted them, which explains why Patty has started bringing antacids when she goes out now.

“Too old to take Ecstasy and go to a rave; too young to go for the Early Bird Special.”

So what are we single, vital people to do?

On the phone one day, I agreed with Patty that dating isn’t the playful, low-stakes situation we both remembered. We’re in scary, unfamiliar territory. Too old to take Ecstasy and go to a rave; too young to go for the Early Bird Special.

Then came an epiphany. As we chatted and chuckled, I realized how much I liked talking to this woman. So I asked Patty if next week she would meet me at the park with our dogs and hang out. I promised to leave my cell phone at home.

That would be our date.

With obvious relief, Patty said this sounded great. Plus, she promised not to mention her biological clock. I laughed and said I’d see her then.

As I put the phone down, I realized I didn’t know how that day would go. But I was sure of one thing: This was somebody with whom I felt comfortable. She wasn’t desperate, crazy or prone to doing Big Ben imitations.

Sitting there, I also couldn’t help but think of something simple, yet profound. Patty was what these other women were not: a friend. And, you know? As far as dating? That seemed like an awfully good place to start.


Peter Gerstenzang is a humorist, video director and journalist. He writes about rock, pop culture and humor for Esquire, Spin, MSN and Next Avenue. This article originally appeared on Next Avenue

Find Peter on Twitter


Christine Crosby

About the author

Christine is the co-founder and editorial director for GRAND Magazine. She is the grandmother of five and great-grandmom (aka Grandmere) to one. She makes her home in St. Petersburg, Florida.

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