I’ll be honest: while I’ve never had a terrible first date, I probably get a little too much enjoyment out of reading other people’s horror stories.
It’s entertaining, share-worthy, and a great reminder that sometimes it’s perfectly fine to skip a date if you’re just feeling sorry for someone.
And if you need a break, grab a cup of coffee, and read up on some shocking stories, there’s no judgment here—that’s exactly why I put this list together.
So, take a few minutes, appreciate the fact that people are willing to share their cringe-worthy experiences, and have a good laugh.
Side Note: Using stock photos for these stories made them even funnier for me.
JUMP TO SECTION:
1. Not Just One, But Two
“Over dinner, he was on his second glass of wine and started crying over his ex-wife. In fact, it was his two ex-wives.” — Winter_Way2816
2. That Hurts Bad
“I was set up on a blind date with a guy. He took me to a party where I knew no one. He then proceeded to flirt with every girl in the room and even left with another girl.” — rowenaravenclaw0
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3. Just Not Enough Money
“Had a girl try to convince me to cut off my long hair for the date. The first date. She knew I had long hair, it wasn’t a blind date. She also brought her dog unannounced, insisted it go into the bar with her, then only talked about money for the next hour or two, constantly pestering me about how much I made. The second I caved in the date was over. Ms. Moneybags still let me pay the tab.”— Unknown
4. You Should Know as Much as Me!
Date: Brother-in-law’s brother
“It was at his company’s Christmas party. While on the date, he tried to make conversation with me about photography – something we both liked – but wanted to talk super-technically about equipment.
He became irritated when I didn’t know anything about my camera or lenses, etc. He proceeded to get drunk and belligerent and kept loudly talking about the fact that I wasn’t having a good time. We obviously never went out again, but he was family, so I got to see him a lot. He’d always just hyperventilate when I came into a room.” — margaretb49238f5cc
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5. Bringing Your Brother Seems Like a Valid Move
“One girl brought her brother along and they stole my roommates pay check off my living room table.”— Unknown
6. Recycling is an Unforgivable Sin
“My favorite one was I picked up this girl and she gets in the car and before even saying hello or anything. she asks me:
“Do you recycle?”
and i’m so blown back by this question, and pause for a second:
“of course who doesn’t recycle?”
and she just says:
“we’re not gonna get along.”
should have kicked her out of the car lol.”
— Unknown
7. It Was Her Loss
“I was talking to someone online once who went on about having bad oral hygiene. I was totally turned off but tried to be polite and said he should set alarms for reminders, he said it didn’t work and needed someone to remind him.
He also said he had such bad social anxiety that he needed someone to make doctors appointments for him. That’s valid, but it wasn’t what I was after in a romantic relationship. I politely told him it wouldn’t work but thank you. He literally told me it was my loss. 😂” — simplysarahish
8. Concerning Food Choices
“I was seeing a food editor for a while, and to be fair, at the start he was really lovely. Engaging, interesting, funny; all that good stuff.
That said, you know how when a chef comes home from work, often the last thing they want to do is cook? Well, I’m guessing he had that, but for eating good food. Because when I tell you that every time he chose a place to eat, I developed a new food phobia, I mean it.
His work took him to loads of fancy dinners and Michelin-starred restaurants, so I understand if he’s sick of THAT (take me to an old-fashioned caff or run-down local gem of a restaurant any day). I’m not fussy at all, and I love stuff like chicken livers and pickled cherries. In other words, it’s not a money thing or an ‘unadventurous date’ thing; he just had a truly shocking palette.
His culinary offerings included: undercooked pub cocktail sausages inexplicably coated in honey, a bowl of genuinely inedible bacon-flavoured corn puffs, and unsalted bread that was still a gummy ball in the middle. It was meant to be a San Fran-style sourdough loaf.
It turned out he wasn’t particularly into me and had been seeing someone else the whole time, so maybe I should have taken the horrible food as the hints they probably were. Just remember, ladies — a pack of mini pickled onion-flavour cured sausages is not likely to come from someone who cares about you.” — aglover
9. Cheating + Cops Called
“Good date. Having fun. Good conversation. Enjoying the nice spring weather on the porch of a Mexican restaurant. We have just asked for the check and then a woman shows up and threw her keys at his face. He pretended it didn’t happen. It comes out (pretty quickly) that this was his girlfriend. They get into a right proper fight in the parking lot and the cops show up.
I can’t leave because my card is inside with the server and it’s taking 1000 years.” — mophilda
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Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.
