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Still Dating After All These Years

What do you do when lasting love seems as elusive in your 50s as it did in your early 20s?

By Peter Gerstenzang

When I first began dating, in my early 20s, it’s safe to say that I was pretty much just interested in the sex. Just as it’s safe to say that when Muammar Gaddafi ran Libya, he was pretty much just interested in state-sponsored terrorism.


In other words, as much as I hate to admit it, I wasn’t looking at the women I went out with as actual people. Who could turn into lovers. Maybe even friends. I was just so hormone-driven I was simply hoping one might be kind enough to sleep with me. Eventually, a couple of lovely women did — after I’d racked up so much credit card debt, I thought I’d have to call one of those late-night TV budget counselors to help me pay it off.

Then things changed. Unfortunately, not for the better. After a couple of years of playing in the minor leagues of sex, I got called up to the bigs. That is to say, I became pretty good at The Act. It wasn’t quite so difficult, or novel, as it once had been. But you know what was hard? The realization, many years later, that I’d spent so much time obsessing over sex, the chance of a real relationship was slipping away from me.


It happened slowly, and then suddenly. All at once I found myself facing the cold fact: I had been dating for more than 30 years! And I was no closer to finding lasting love in my 50s than I had been in my early 20s. I won’t lie to you: I was scared. It was pretty unsettling to realize I’d been dating since Phil Collins had a hit with “Sussudio.” When it came to having a relationship, I couldn’t close the deal. Or pull the trigger. Or whatever expression it is that those tough guys in David Mamet’s plays are always using.


I’d come pretty close to marriage on two occasions, and both times received ultimatums. Which were totally reasonable. I understood about the biological clock. The problem? Neither relationship seemed quite happy and harmonious enough to stop me from holding back. Maybe I just wasn’t the marriageable type. Despite what Old Blue Eyes sang, love and marriage don’t always go together. At least for some of us. But what did that mean, I wondered, for those of us who couldn’t marry? Would we be consigned to a life of abject loneliness, like a character in a sad Sinatra song? Alone at the end of the bar, bending the bartender’s ear at a quarter to 3?


Recently I took a walk, and everywhere I looked I saw white-haired men — old versions of me — walking alone, talking to their dogs. Was that going to be my fate? If so, I planned to fight by any means necessary! I went home and made some frantic calls.


I hadn’t been “set up” in a while, but was confident my friend Rick could help me. He was certainly aware of my love for all things Italian: Fellini, gnocchi, Ronnie James Dio. A blind date with an Italian-American would be perfect. So when I went to that bar to meet Missy, a blonde accountant, I had high hopes.


Two minutes into our conversation, she made her one and only reference to Italian culture.


“So, who’s your favorite on Mob Wives — Drita?”


I waited for her to smile and say “gotcha!” No dice. I soon realized this wasn’t really a set-up — it was a hit. Sinking into despair, I finished my meal. I saw Missy one more time. And, OK, we had sex. Hey, I’m a guy. It’s in my service contract. But the experience felt much emptier than when I was 23.


After that, I went online. I “met” Katie on a social networking site, whose name I can’t mention for legal reasons (suffice it to say, they made a movie about the site and the shifty little weasel who founded it). Katie and I exchanged pictures, talked about rock, made fun of Twilight. It was great. We quickly progressed to sending each other e-mails — nothing too salacious; it was all good fun. Till I accidentally sent one to an editor whose first name resembled Katie’s. He told me that I should be more careful. And that I was in desperate need of counseling.



This was the wake-up call I needed. I still had time to change my destiny. So I asked another friend for a fix-up with a woman in my age group, someone with whom I could talk about La Dolce Vita.


Such things seemed possible when I met Sarah. She was as funny as Joan Rivers and as cute as Lauren Graham. We had three terrific dates. Her conversation was so smart and challenging, we nearly forgot about the sex part. But things went south — and rather spectacularly, too — the first time we went out to dinner.


I picked the restaurant, which made me feel safe and in control. Then again, that’s how Virgil Sollozzo felt, right before Michael Corleone came out of the bathroom and shot him in the head.

Dinner talk was sprightly, but Sarah kept being interrupted by texts and disappearing. Each time she returned, she seemed a little more upset. I asked what was wrong. Apparently, she and her ex were having a trial separation. He missed her. She, him. Sensing disaster, I said she should probably go. Sarah jumped up and was out of there before I could add, “On the other hand...”


I went home, certain I’d stay there until I was found, at the age of 87, buried under a welter of sports magazines and Stouffer’s Frozen Entrees. I whined. I wept. After several days of this, I straightened up and decided I was going to meet somebody on my own, with no outside involvement.


Over the next few weeks, without social networking or help from friends, I got together with Louise, a teacher who’d read one of my articles and contacted me through my editor. Mostly we talked. About politics, our favorite bands. No one mentioned Mob Wives. Given my last three dates, this was a something of breakthrough. No romance blossomed, but my evening with Louise provided warmth and cheer. And something more: It gave me hope.


Equally important, I’d proven something to myself. As far as love and companionship go, I was growing up. I'd come to understand on a deeper level that a lasting relationship with a woman involves friendship and a true connection. And in the wee small hours of the morning, that's what really matters.


Peter Gerstenzang is a humorist, video director and journalist. Read More
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