We all dream of the perfect first date—filled with connection, chemistry, and maybe even a bit of magic. But let’s be real, not all first dates live up to our expectations. Sometimes, they go so wrong that you can’t wait to make a quick exit. Here are a few jaw-dropping stories of first dates gone hilariously off the rails.
1) Dinner Disaster: The Waitress to the Rescue
I went on a first date with a girl who insisted we dine at a fancy restaurant. I wasn’t too worried about it at first. She ordered a $25 appetizer, a $45 steak, and a $15 drink, which seemed excessive, but I thought, “It’s just one night.” The real problem started when she wouldn’t put down her phone. She was constantly texting and even taking calls during dinner! I felt invisible. To my surprise, the waitress must have noticed how awkward the situation was. She motioned for me to come over while my date was distracted. When I excused myself and spoke to the waitress, she had already prepared separate checks and asked me, “Do you want to just pay your share and leave?” It was like music to my ears! I said, “That sounds perfect,” paid my part of the bill, and walked out, leaving my date with her steak and her phone.
2) Dodgeball Debacle: An Escape Before the Game
This guy invited me and a friend to join him and his buddies for a dodgeball game. It seemed harmless enough at first. He spent most of the time with his friends, but I didn’t mind because my friend was there to keep me company. Just as we were about to start, he grabbed a dodgeball and hurled it directly at my crotch with full force! To make things worse, he yelled, “Wham, bam, right in the clam!” I was completely mortified. I immediately turned to my friend and said, “Let’s get out of here.” We didn’t even stick around to play the game. On the way home, I received a barrage of texts from him, calling me “immature” for leaving. Yeah, I don’t think I’m the immature one here!
3) Strippers and Soldiers: The Date that Derailed
I once went on a date with a guy who was in the military, and I thought it would be interesting to hear about his experiences. Unfortunately, he spent most of the night talking about how the strippers in Toronto were better than the ones in our hometown. Trying to steer the conversation in a different direction, I asked if he had done any volunteer work overseas. His response? “No, I joined the military to kill people, not help them!” That was my cue. I paid my bill, chugged the rest of my drink, and left without looking back. Not the kind of military story I was expecting.
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4) The Stalker Vibes: A Bartender Saves the Day
Within the first 10 minutes of meeting this guy, things started to get creepy. He made sexual comments right off the bat and even joked about following me home if I didn’t want to see him again. I was seriously freaked out. Luckily, the bartender noticed my discomfort and discreetly helped me sneak out the back door. I’ve never been so grateful for a quick getaway.
5) Online Dating Nightmare: A Date to Forget
I matched with this guy on a dating app, and when he showed up, I knew something was off. His pupils were huge, and he was acting erratically. He told me he had forgotten his wallet, so I covered the first round of drinks. As we walked to another bar to meet his friends, he rambled on about nonsense and then casually mentioned how he tried to drown his ex’s chihuahuas. That was the final straw for me. When he took a phone call outside the pub, I said I’d meet him inside, but instead, I kept walking and ran all the way home.
6) Drunk at Lunch: A Quick End to a Boozy Date
I went on a 1 p.m. lunch date with a woman who showed up completely wasted. She was slurring her words and invited me back to her place, assuring me that her two-year-old son wouldn’t even notice. That’s when I knew it was time to bail. I called her a cab and got out of there as fast as possible.
First dates don’t always go as planned, but sometimes they turn into stories you’ll be telling for years!
