GRAND Magazine - July/August 2018 - 6

romance

Midlife dating: one man's epiphany about looking for love
BY PETER GERSTENZANG

ack 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
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MAY JUNE 2018

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 I 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
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: 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

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.
Click here to continue

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

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GRAND Magazine - July/August 2018

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