Probably the most frequent question I’m asked from friends and first dates alike, is “what’s your worst date ever?”

Oh, there have been some unpleasant moments, like the grouchy guy that was irritated that the restaurant I chose didn’t serve bourbon. There was the cheapskate that insisted on splitting the cost of one single, pot of tea. One man waited two hours into our date to tell me he was still legally married.

But it wasn’t until this last December that I have a definitive “worst date ever” story.  

We had matched on the dating app, Hinge, and quickly started speaking on the phone regularly. The conversation flowed easily. We had a lot in common. I felt a genuine connection. He checked those proverbial boxes — successful professional, kids out of the house, well-educated — and he said the right things to me, making me feel respected and admired. We made plans to meet after Thanksgiving.

Unfortunately, I caught Covid (1st time). Then a week later, he did. After Christmas, he finally tested negative, and we planned our first date. I was excited to meet him.

We already knew so much about each other that our conversation was “how did that meeting go?” rather than the typical first date questions like, “how old are your kids?”

“This doesn’t feel like a first date,” I said to him, while seated at the bar.

“You’re so cool,” he said to me. “Everything I’d want in a woman.”

After nearly four hours, some food, and quite a few vodka sodas (me, following each cocktail with a glass of water), things got flirtier, with a little kissing and touching. We made plans for the next date.

When it was time to go, he got off his stool, weaved his way to the door, bumping into chairs and tables like a ball in an arcade game.

‘Oh no. Is he drunk?’ I thought. 

In the cool night air, I stepped off the curb, looking up and down the empty West Village streets for a cab.

“I think I’ll walk east a couple of blocks,” I said.

“I’ll walk you,” he said, then tripped off the curb behind me, did a ungraceful (disgraceful?) pirouette, bumped into a parked car like a pinball, and dropped to the ground on his ass.


While he struggled to get up like a turned-over turtle, I swiftly pulled him up to his feet, knowing that I will have to walk him home. Instead of a romantic evening of handholding, I took his to keep him from wandering into the street like a toddler, saying to myself, ‘please don’t vomit.’

I rationalized: He IS coming off Covid. Everything was going so well until now. This is a one-off, right? I like him so much.

At the same time, I was embarrassed to be seen with him; angry I had to babysit him; and disappointed in yet another man. Any attraction I had for this man was blown away like litter in the evening’s Hudson River breeze. 

A few days later, I told him that I liked him, but his behavior was a turn-off. He apologized profusely.

Despite my friends saying, “hell, no,” I went out with him two more times. He was on his best behavior. I had hopes that his charm would override the memory, but I couldn’t “unsee” that first night — him, hunched over, head hanging, lurching in an S-pattern down the sidewalk.

Naturally, the calls stopped. I missed our evening catch-ups — filling him in on my day; him asking my opinion on his projects. This man was soooo close to what I’d been looking for.

The upside? Now, I had a good answer for, “what’s your worst date ever?”

Great Guy, But Worst Date Ever was last modified: by

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