Finding love in this digital era is far from easy. With more websites and applications — in which we can essentially 'shop for people' — than we know what to do with, the influx leads to infinite choice, infinite possibility, and infinite encounters that are often so bizarre, they could be fictional. But by embracing the good, the bad, and the downright ugly of the online dating minefield, at least bad dates make great stories. Right?
Together with The Single Society, we are bringing you the hilarious, horrible, and awkward real-life stories from women currently navigating the world of online dating. When you're finished reading this shocking tale, check out our other true stories of modern dating debauchery.
This was the worst dating fail of my life.
It met Jimmy as my 33rd birthday was rapidly approaching and the number of single friends I had seemed to be dwindling by the hour. However, this dating fail made me realize that being single is really not so bad. For some reason, I thought joining OkCupid would be the perfect way to start getting my sh*t together.
Jimmy looked good
Jimmy suggested we meet at an elegant restaurant downtown after work one evening.
Jimmy had adorably boyish features and was an unpretentiously dressed New Jersey native who worked as an accountant for the Chrysler Corporation.
Until he opened his mouth.
This 'conversation' actually ended up being quite nauseating.
It was PAINFUL.
Jimmy, a self-proclaimed sci-fi enthusiast was apparently in the process of composing his own manuscript that could only be described as the love child of 'Star Trek' and 'Game of Thrones.'
Jimmy would not shut. The. F*ck. Up. about this stupid mother f*cking novel.
He went on about the various plotlines, the character development, where he sources his inspiration…it didn't stop.
I sat there wishing for him to shut the f*ck up.
He even went so far as to retrieve a notebook from his laptop bag and made me read the first three pages of the prologue.
Finally, the waitress came to take our order.
He went ON AND ON about his stupid novel.
No such luck. He ordered a starter and the lamb chops as his main course which just so happened to be the most expensive dish on the menu.
Jimmy continued on about his novel and other topics in which I was completely disinterested or paid no attention to.
The bill came. He asked to go Dutch.
Alas, the check came and I pulled out $35 after adding up my $15 salad and two glasses of wine in my head.
"Yes, of course," I replied, as I placed my cash on the table.
Jimmy instructed the waitress to take the cash for my portion and put the rest on his credit card.
His card was declined. Shocker.
The waitress returned and informed us that the credit card had been declined.
Jimmy (clearly abashed), rummaged through his wallet and then his laptop bag in search of an additional card that obviously did not exist.
I just wanted to get the hell out of there.
"Ahh. Sorry, that's embarrassing," Jimmy said. "I appreciate it though!"
So much for going Dutch.
If I weren't such an anti-confrontational wuss, I would have demanded he Venmo me then and there, but I decided I would spare him from further humiliation.
Take me home to my cat!
We exited the building and after an awkward side hug and a quick goodbye, I finally took solace in the privacy of my vehicle, and the fact that I was one step closer to being in bed snuggled up with my cat.
"Not so fast," said the universe.
It was the most deadbeat date of my life!
I pulled up to the exit of the parking lot to pay the parking machine and the car in front of me was taking their sweet time. Suddenly, Jimmy popped out of the driver's seat.
I rolled down my window.
Jesus H. Christ.
I didn't have any more cash on me either, so I gave him my Visa and he ran to the machine.
Oh. My. God.
"WHAT'S YOUR ZIP CODE?" He yelled.
I relinquished my zip and he returned my card with yet another quick farewell.
Finally, my awful evening with Jimmy was over and he was (thankfully) never heard from again.
About the AuthorTheSingleSocietyNikki is currently living in NYC with her husband (who she met on Bumble after experiencing the absurdity of online dating) and working in digital marketing. She clearly enjoys recording the ridiculous debauchery that is the modern dating scene. Nikki is also partial to a tall glass of Prosecco, her black/calico kitties, 90s music and playoff hockey. Drop her a line if you have a good story for her to write about.