February is best known for Valentine’s Day, and to keep that Hallmark Holiday real, we asked Overcast readers to tell us a tale of a date gone wrong, way wrong.
1.) The Long Con? …
Me and this guy start talking on Tinder. He finds out I’m a movie buff too. We bond over being a dying breed of people who still collect DVDs, even VHS. It was cute, like, we talked about when Jumbo and Blockbuster went out of business and how the clearance sales were goldmines for cheap DVDs.
Anyway, after 2 weeks of swoony chatting, he texts me from The Ship at 1 am. I’m down the road, just about to leave a party. We hook up. It was awkward, fumbly, greedy — that wasn’t the surprise. He was gone the next morning, and so were — I discovered weeks later — my boxsets of The Wire, and some movies! He’s not on Tinder anymore to confront him, but c’mon, I think this was a con!”
2.) The One with the Manager’s Son …
I was set up on a date with my manager’s son. He started texting me a few days beforehand and told me he was going to take me to The Keg. When the night came, he showed up at my door with a case of beer and blood on his shirt.
He said he went to a bar beforehand to have a few drinks because he was nervous, and the blood on his shirt was from a bar fight he had gotten into. This should have been a sign to stay home, but I was young and stupid so I left the house with him.
Once we were in the cab he tells me that The Keg is closed for renovations so we will be going to Montanas instead. This was a lie, The Keg was opened. Once we get to Montanas he decides he is going to sit on the same side of the booth as me and try to kiss me. He was being very loud saying “you’re so beautiful, I know you want to kiss me” and I was so embarrassed.
I think he could tell, so he finally moved to the other side of the table. Once the meal was done he looks at me and says “Oh no, I forgot my wallet.” So I ended up having to pay for both of us! I just wanted the date to be over so I paid and called a cab.
Then he jumps in the cab with me and says he wants to bring me to my door. Once I’m at my door he tries to force himself on me to the point where my male roommate heard me saying “no, stop it,” and he came out and saved the day. He made my date leave and I never saw him again. I was pretty horrified at first, but now it’s a funny story to tell.
3.) The Date So Bad It’s Questionably Real …
I met a girl over plenty of fish. Picked her up for a coffee and a drive. She wanted to be picked up at the Avalon Mall (first flag), but I gave her the benefit of the doubt, thinking I could be a serial killer or what not. She then gets in my car, proceeds to be grossed out by my beard, and then asks if I can do her a favour.
She wants to know if I can pick up her mom at the DMV. Me being the nice guy I am said sure. As she rushes me to get to the DMV, she proceeds to be rude and annoying. “Mudder can’t wait all day,” she says as I’m driving through traffic. I arrive at the DMV, she gets out to grab her mom. Then the rest of her family walks out as well; her 11 year old sister, her mom, and large white male we will call ‘Tiny,’ who was recently just out of the slammer.
I let this girl have a smoke in my parents’ car I was driving, because of them being out of town. Of course her entire family lights up a smoke each when they get in, including the 11 year old sister. They go through 2 packs in my car while I drive this family around to do errands. Next thing you know I’m waiting outside Sobeys while they get/rob groceries (Classic Tiny), then proceed to drop them at the mall to buy a dress.
Then me and Tiny had to run a special errand, of course. After that, and picking them back up at the mall, I then dropped the parents home while we picked up more smokes for the 11 year old girl who was fresh out. Backing out of the store, I bumped into a car after just having my licence for 3 weeks. Thank god nothing was done and both cars were fine so we went about our day.
I dropped this girl’s sister off, and then she rushed me to bring her to work. Finally I think this date from hell is over and she calls saying her mother left her jacket in my car. After I cried knowing I would have to see her again, I dropped it off at her work. She then proceeded to call me and accuse me of robbing hundreds of dollars out of her mom’s jacket with credit cards too.
I laughed and hung up as this clearly must of been a thoughtfully planned out skeet sting.
4.) That Time You Sent Your Cousin a D-Pic …
I don’t use a pic on Tinder or PoF, etc. I don’t use my real name. Unwittingly, I got a D Pick from a close male relative, cold, bam, out of the blue. And now I can’t look at him on family get togethers without thinking PERV, or feeling breached in the worst kind of uncomfortable way!
5.) The Frozen Blueberry Freak Out …
This guy was the sweetest, seriously. We agreed to meet for supper, got tipsy, ended up heading downtown together to meet some of my friends. And then, because it’s a winter wonderland out there, we agree to go sliding, on a hill back near his place.
We were drunk, so there were some tumbles, of course. But I’m a tough broad. or so I thought. I ended up back at his place (fill in the blanks!) and woke up to pee. I was still hammered — we’d been drinking straight through from 7pm until 2 am. When I went to haul my underwear down to pee, it was like a dog had bitten my wrist, that’s how much it hurt. It was starting to swell, so I went to find ice, to ice it, instead of you know, just heading home!
The reason I mentioned “I was still hammered,” is because I thought this was a good idea: He had ice, but I couldn’t find a ziplock or Dominion bag and decided a bag of frozen blueberries would do the trick! Back to bed I went. I woke up to him shouting. There was a bright blue pool near my vagina, because the bag burst open, and he thought the worst had happened.
6.) The Merchant Tavern Mortification …
So, I’m at Merchant with a really great Tinder catch. Out of my league, catch my drift? Then a person comes charging towards our table. The person was this older woman I was hooking up with, but called it off, because she was extremely paranoid and jealous and possessive immediately. Worried I was texting other women when she and I were together, or that I was flirting with a cab driver, etc.
Anyway, I ended it, and thought that was the last of her, until I’m at Merchant with this smart babe, and this crazy old lady comes barrelling over, and begins to tell my date all about how untrustworthy I am, how I’ll drop her ‘like a hot potato when someone else comes along,’ and even that ‘he probably has the smallest dick in this room.’
Needless to say, mortified. I mean, on at least 2 of 3 of those warnings, this lady was out to lunch, but, why wouldn’t my date believe the rambling mad woman? She must have. That was our second, and final date.