Weekend Conversation: What’s Your Dating Nightmare?

Its no secret that the best laid plans often unravel into an awkward mess when it comes to dating. You wind up in traffic, the restaurant loses your reservation, it’s the hot air balloon operator’s first day, you find out that you were being catfished, or SOMEONE TRIES TO FRAME YOU FOR MURDER — these things happen… probably. The point is, on some level, you probably know something about nightmare dates, so, we asked our staff to spill their guts (literally, in one case) and talk about their own hellish experiences. And since you are good people, we know that you’ll pick us all up by sharing your own experiences in a, “Hey, buddy, I get it” kind of way in the comment section.

When The Wheels Fall Off

Back when I was in my early 20s, my now-wife picked me up from work in high heels and a party dress. We hopped in our pickup and headed straight for the bedroom (sorry, but it’s true). Sadly, we were diverted when we hit a massive pot hole and cracked our rear axle. I’m not sure if the prospect of spending hundreds of dollars on a piece of crap truck or the tight fit in the tow truck served as the ultimate cooler on that night, but unsurprisingly, no sex was had.

Evening Gone Sour

My roommate’s girlfriend at the time had been telling me for weeks how I would hit it off with her co-worker. After exchanging a couple of emails, we eventually agreed to go out for drinks and planned to take a water taxi over to Long Island City in Queens to check out a couple of bars. We weren’t meeting up until 8, so I scarfed down some of the leftover sweet n’ sour chicken I had in my fridge before the date. I should point out that it was from Thursday and it was now Saturday. I should have known better. A combination of rough waters and two-day old Chinese food eventually took its toll and I yaked over the side of the boat before we even made it to shore. Our date started at 8 and was over by 8:30. We haven’t spoken since. –Bennett Hawkins

Unlucky Condom

When I got out of college, freshly broken up, I did the online dating thing and met a few women. I had a condom in my wallet, although I wasn’t optimistic, but I stopped doing that after my first coffee date, when I took out my wallet to pay and the condom fell out. Into her latte. On the bright side, at least she let me down easy when I emailed her to apologize. –Dan Seitz

Dinner-Date Gone Wrong

The summer after I graduated high school, I went on a date with a girl who was a bit out of my league. I knew her prior to the date, so looking back, I’m not sure what the circumstances were that I even made it happen, but I was nervous from the start. I took her out for dinner, and almost immediately, I spilled a good portion of my chicken parmesan right onto my lap. For the rest of the night, including the movie — why didn’t I suggest we go back to my house so I could change? — I had red pasta sauce covering my pants and a good portion of my shirt. We did not have a second date. In fact, I don’t recall ever seeing her again. But we’ll always have that one magical night at Olive Garden. –Brian Sharp

Too Stoned

I had a date in Prague once where I was too stoned to hold a conversation. So my date just paid for her tea and left, and I decided to smoke the shisha we ordered and I literally passed out. –Zach Johnston

Goodfellas-Style Double-Date

It was a Goodfellas-style double-date scenario: an old co-worker of mine wanted to go on a date with a girl, but she’d only do the date if he could find someone to take out her roommate. I decided to go along, and from the moment we arrived at their house, I could tell the roommate wasn’t into it — like, at all. I did what I could to try and have a nice time, but it clearly wasn’t taking.

After dinner, the girl I was out with got up to use the bathroom. That’s literally the last I ever saw of her.

Weird and embarrassing as that was, it didn’t hold a candle to the awkwardness to the fact that my co-worker was my ride home, as was the girl he’d taken out. Both of whom completely ignored the awkward turn of events that evening, opting for mindless small talk instead. –Christian Long

So, what’s been your worst date nightmare?