May 23, 2022

Expanding Horizons & Deflating Dreams: Tales from the Dumpster Fire that is Online Dating.


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Everyone has a story that defies all science and reason. My grandfather, Max, smoked two or three packs of unfiltered cigarettes every day since World War II, and if that wasn’t outlandish enough, he also drank coffee from the moment he woke up right up until bedtime. He would brew a couple of pots and then microwave it all day long.

This sounds like a recipe for a short and miserable life, but he outlived my mother and my father and went to his grave whistling a happy tune somewhere around 80 years old.

I always tend to reflect on this when someone tells me about their friend who won a million bucks from a scratch-off ticket or, even more unbelievable, found someone online and lived happily ever after. I mean, sure, people win jackpots and find true love through Hinge, but it’s not a basket I’d feel comfortable putting all my eggs in.

I’m a realist. It’s why I quit smoking 12 years ago instead of hoping I’d follow in my grandfather’s precarious footsteps.

Not to mention, even if I could be assured that I would definitely get the big payoff after a hundred dates, I’m not sure I’d make it the whole distance. Bad internet dates have been relegated to the same file as flight cancellations and death-defying near misses on America’s highways. They are enough to traumatize you, but when you get ready to tell someone your story, you stop. Everyone has experienced it, and no one wants to hear about it. It’s boring.

That being said, there are some bad internet dates that go so far beyond the pale, they really capture the essence of the dumpster fire that online dating truly is.

I’m single and I know a few women, quite intimately, who are as well. And not every person who is single finds themselves that way because they are the problem. But it becomes painfully obvious when you go out on a date with someone and see their profile two years later (usually with the same pictures), that there are people who really are their own worst enemies.

A few years ago, I was in the middle of a pretty depressing breakup when I decided to reactivate my Facebook dating profile and get myself out of the house. I happened upon a woman who was also a writer and I sent her a cute message. If I remember right, she was about 10 years younger than me, and her pictures looked pretty sexy.

We seemed to hit it off well and were messaging four or five times a day. I noticed one of her prompts mentioned her favorite restaurant, so I asked if she’d like to join me there for dinner on a Saturday night.

Smooth, right?

Well, she, of course, said she’d just love to, and the date was on.

If I’m not mistaken, Ruth Bader Ginsburg had died that day and we were still quite a ways away from a Covid vaccine, so even though it was about 40 degrees, we opted to sit outside. The restaurant had these wonderful propane heaters that made it a toasty 43 degrees, so at least we could be comfortable while we ate—as long as we didn’t take our coats off.

She had the extra advantage of the $18 glass of Chardonnay, but I wasn’t going to complain. I figured if she had a drink, the conversation might be interesting. And I wasn’t that far off the mark. The server hadn’t gotten four feet away from our table before she admitted to me that she typically dated younger men.

There was a pregnant pause and then I finally asked why she agreed to our date, as I was, in fact, 10 years older.

“Well,” she said, “Things haven’t been that great lately and I figured I should expand my horizons.”

I let it go, but I will admit that on an emotional level, it was as if I was on the starting line and someone just took half the air out of my tires. Maybe it was the combination of being wedged inside of an uncomfortable breakup and feeling self-conscious about my age, but there I was.

She changed the subject to what most liberals were worried about on that particular evening—the GOP installing a hyper-conservative judge in RBG’s place and dismantling 50 years of women’s rights (it’s a good thing that didn’t happen haha…). I held my own in the verbal thrust and parry until she slipped in this non-sequitur about “usually dating taller guys.”

Again, I let the conversation go silent before finally asking, “Well why did you agree to go out with me? My profile clearly stated that I was 5’ 6”.”

“I told you, silly, I was trying to expand my horizons.”

Expand your horizons or deflate my checking account? I thought when she asked the server for a second Chardonnay.

And as that second glass began chipping away at the two or three inhibitions she had left, she managed to let it slip that she always found it difficult to date guys with children.

“Well, I’m glad I could be such an integral part of your horizons being expanded.”

She smiled, tentatively and weak, and I shook her hand before I paid the bill.

On the depressing drive home, I stopped at the convenience store and bought a pack of cigarettes and a scratch-off ticket. I figured, at least in terms of simple mathematics, something was bound to go right.


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