First Date Horror Story


If anyone truly knows the incredible highs and staggering, depressing lows of dating, it’s me. I have never been particularly blessed with stunning good looks, and so I tend to rely on my sparkling personality to win people over and get the oft-coveted Second Date. A while back, I had become accustomed to striking out, and wasn’t feeling particularly confident, and so I had gotten a bit…lax in caring about the outcome of my uninspiring dates.

This is the story of how I met my current girlfriend.

It was not an auspicious beginning. We had never met in person before, and despite our mutual friends saying things like, “You will love her!” and, “She likes Billy Joel, too!” I was feeling less and less confident as the day for our blind date approached.

It was to take place a Saturday, the day generally reserved (for me, at least) for battling headaches over very large cups of coffee, and it was also going to be during the day which, as we all know, is the absolute worst time to have to look at another person and try to be cheerful and ‘on’. After a night of heavy drinking the previous evening, I was—to put it mildly—looking and feeling like absolute shit. I had woken up late, which resulted in me having to make an unpleasant decision: shave my legs, or pluck my eyebrows. Since I was not planning on removing my pants on the first date, I opted to groom the blonde caterpillars that live above my eyes. Then, I found a sensible pair of jeans on my closet floor, a Cool Distressed T-Shirt (which was actually just a very, very old Rush t-shirt that I had owned for about fifteen years), a pair of cute flats, and was out the door!

It all went to hell quite quickly after that.

I arrived at the restaurant to find… let’s-call-her-Kelly already waiting.  She had been waiting for the past forty minutesI had botched the time and, thinking I was a few minutes early, was actually several dozen minutes late and rather embarrassed. She waved off my gross miscalculation of time, and we ordered drinks. Well, I ordered a drink; she ordered a lemon water because Kelly doesn’t drink. When I ordered my duck-and-ricotta lasagna, I also found out that Kelly is a vegetarian.

As I sat there in shame, eating meat and drinking alcohol, my shame growing exponentially, I finally mumbled a quick, “Be right back,” and ran to the washroom. I stared at myself in the mirror, wondering how on earth this absolute angel had been putting up with me, and then I chalked it up to a combination of being partially blind and possibly a little slow. Slightly heartened by the fact that she might not be able to see my sorry, hungover state, I did a quick mirror check and found out painfully late that there was a reason the jeans were on my closet floor: there was a large, greenish stain on the left ass cheek from when somebody the previous evening had spilled some stupid, fancy drink down the back of me at the bar.

Head hung low, I returned to my seat, having realized that there was no need to hide it: she had likely already seen the stain. I plopped down and took a swig of my Bloody Mary, and a bite of my rapidly cooling duck lasagna, and looked across the table. She was smiling. I must have looked confused, because her smile widened to a grin, and then she started laughing. I raised an eyebrow, wondering vaguely if I had inadvertently told a very funny joke when I sat back down at the table.

“That was me,” she explained. I looked at her, deadpan. “The drink,” she elaborated, gesturing to me. “It was a virgin mint julep smoothie. I tripped and spilled it on you.” She looked down at her vegetable medley pasta and poked at the noodles, looking somewhat embarrassed.

I sat quietly for a minute, then looked over at her and whispered, “That shit was cold”. She looked up from her food and across the table at me, and we both burst into laughter. She—angel that she is—agreed to a second date, which turned into a third date, a fourth, a fifth, meeting each other’s parents, two awkward family dinners, a lot of off-color but well-meaning comments from my father, an inappropriate-yet-hilarious gift from her grandmother, and two years later we’re still going strong. She still doesn’t drink, or eat meat, but we both love Billy Joel, and we love each other, and that’s what’s really important.

So don’t sweat the small stuff. Don’t worry about the first date, because even if it’s embarrassing and horrible, there’s always a chance there might be a second one. Got any dating horror stories of your own? Share your own experiences here or let us know on Twitter @GFMDating – if you dare share, that is.