Dear Pandas, how's the dating scene treating you? Whether you're happily coupled up, blissfully single, or caught in some kind of situationship, we're sure you've got a story or two tucked up your sleeve about those wild and unpredictable encounters known as first dates. It's the 21st century, after all — a time when the quest for love, or just a decent evening out, has morphed into this rollercoaster ride of swipes, winks, emojis, likes, and an alarming amount of ghosting. And every so often, these romantic quests gift us with funny dating stories, where our dreams of romance crash with reality in the most hilarious ways.
Ever braved a Tinder date that made you question your sanity? Maybe your prospective partner took you to a circus for house cats for your first meeting. Or perhaps your funny date involved someone who, out of the blue, decided it was an amazing idea to bring his mom with him. Yeah, it happens. No, we're not making these up. These are real first date stories unearthed during our internet spelunking on Reddit, and we've got a whole load of these that are sure to entertain you as well!
In this world of dating fails and romantic Russian roulette, no matter how many frogs you've kissed or unimpressive pick-up lines you've had to endure, there's always room for a good belly laugh. So whether you're seeking reassurance that your funny first dates weren't quite the trainwreck you thought they were, or you're simply in need of a hearty chuckle, we've got you covered. We scoured through Reddit, and after much laughter and a few tears (from laughing too hard, of course), we're excited to present you with an epic collection of hilariously relatable dating tales. Each one is a beautiful, chaos-filled tribute to the unpredictable adventure that is modern dating — online dating stories making up a hefty chunk, of course!
#21
"Guy I met on OkCupid brought his mom to the date.
It was so awkward, the funniest stuff ever.
So he told me that his best friend was his mother and that they spent a lot of time together. At first, I thought 'Awww that's sweet!' and he talked about her nonstop, her work, her hobbies, and the things she did, he even shared her picture with me which I thought was kinda funky, we agreed to meet at a cafe in town, he hopped out of his mom's car and she waved and drove off, like 20 seconds later she shows back up and pulls up a seat, turns out she was parking the car to come to join us.
The entire date was just her talking about her work and showing me old photos of when she used to play baseball, they sat really close together and kept hugging and kissing each other's cheek, it was so freaking awkward."
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24points
#22
"We were in a fairly empty lounge. There was a TV on with either Jay Leno or Conan O'Brien's monologue. Instead of either chuckling along or ignoring it like normal people do, he decided to dissect each joke and why they are not funny and people shouldn't be laughing at them. He then proudly said he does it at parties and comedy shows too.
People often sarcastically say someone must be fun at parties. I have never met anyone actually admitting to it."
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24points
#23
"He insisted to take me out on a date, and so for dinner, he suggested a sushi place about 30 mins away from our area (we both live on the same side of the city). When it was time to pay, he 'forgot' his card. Alright sure, no problem, I’ll pay. I don’t mind. But for the first time ever, I did not have my card either. LOL. We then told the servers that we’ll be back to pay (I left my license with them).
So he drove all the way back to our area, drove past his house, and drove straight to my house. So I can get my wallet… I assume. So I did.
Anyways we of course drove all the way back to the restaurant so I can pay the bill. So yeah, I left it at that and never bothered to contact him back again. LOL."
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24points
#24
"I was meeting a guy in person for the first time after chatting online for about 3 months. After the first glance, he said 'You’re uglier in real life. Your photos are stunning though'. I wasn’t offended at all - it was too funny."
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22points
#25
"I was having a great night with this guy and at the end of the night he walked me to my car. He wanted to sit in the car with me, which I found odd but whatever. Then he pulls me onto his lap to make out, which felt odd as an adult but again. Whatever.
Now the following day he calls me informing me that since we stayed up so late last night, and he had to work so early the next day, he wore the same jeans from our date to work that morning. What he did not realize, and to my absolute horror, I had started my period while sitting on him in the car. He did not notice until his colleagues pointed out the stain on his pants.
Welcome to my horror story of a life."
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20points
#26
"I had been dating this guy in college for a while, and I noticed he never liked any condiments on his food and wasn’t very creative with any flavors. We went out for pizza, and half of the pizza had pepperoni, mushrooms, and onions, while his half was regular pepperoni.
The next time I see him, he gives me a kiss at the door, and immediately I was like 'Ewww' at his breath. He goes, 'I never realized how good onions are, I read that you can eat an onion like an apple, so I tried it! It’s actually pretty good!'
We didn’t last much longer than that. It was so awkward with his newfound onion obsession. And then I felt bad that I’m technically the one that opened that can of worms."
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19points
#27
"22-year-old guy is eating chicken tenders by cutting them with a steak knife and using a fork and I kind of make a joke about that being weird because it’s finger food. I say this while I’m eating my potato soup by picking out the chunky pieces with my hand. I ATE SOUP WITH MY HAND AND THOUGHT HE WAS THE WEIRD ONE.
Of course, this realization didn’t come until I was retelling the story to my roommate. He still tried to take me on a third date but I declined and told him I wasn’t interested in him. He took my lack of speaking to him as an invitation to show up at my job looking for me randomly for about a month then he gave up."
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19points
#28
"It has to be a dinner date where the guy asks what I like on pizza. I laughed and said, 'I wish I didn't, but I really enjoy eating meat. I like chicken, pepperoni, bacon, and anything else you can think of on a pizza. I know it's not very sophisticated, but damn.' Dude leaves 'Oh, that's cool. Actually, I'm a vegetarian'. I just burst out laughing because I knew it was going to be an awkward 40 minutes."
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19points
#29
"His mom picked me up. She didn’t stay at the restaurant with us but until that moment I had no clue he didn’t have a license."
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19points
#30
"We were trying to decide where we wanted to eat and I suggested Panda Express. She hesitated before saying no. Then I suggested Asian Buffet, but once again no. I got bold and said Benihana. She told me to take her home. She told me later she thought I was being racist because she was half-Chinese. I didn't even notice. I only saw her black dad and assumed her mom was Hispanic or something. I ended up getting KFC."
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19points
#31
"It was a first date. I suggested a cute place to get some coffee. When we arrived, it turned out to be completely full. No matter, there was another nice place nearby. He rejected it because it was 'too far away'. I was stunned because it was just down the street. We could see it from where we were standing. Less than a one minute walk.
We went to a cafe even closer. The date itself was not that bad, but it became clear that we were not a good match. When we asked for the bill, he immediately insisted we split. I prefer that too, but the total was only 4.20 euros (about 5$, we had one soft drink each). It seemed a bit silly to me to split that, so I happily offered to pay for both of us and handed the server a 5-euro bill. What was funny to me was that while I was paying, he came up from behind and gave me a 2 euro coin, proudly saying 'That should cover it!' Lol."
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18points
#32
"Double date with my roommate in our apartment. Both dates were guys we knew from class but had never gone out with before. My date showed up already drunk and proceeded to get drunker. We all watched 'A Knight's Tale' and 10 minutes in he lay down (we were sitting on a couch), put his head in my lap, and kept mumbling "It's just so anachronistic" over and over throughout the rest of the movie. My roommate and her date were laughing at us."
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18points
#34
"One time I had forgotten a Tinder dude's name and we had already talked about people looking at their phones while on dates. I was feeling anxious like for some reason I'd have to say his name so I managed to steer the conversation towards handwriting and signatures. So we both signed a napkin. Then I couldn't read the dude's signature so I said 'Wait, how do you spell your name?' And then he spelled out his extremely common name to me."
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17points
#35
"A guy asked to observe my beer-pouring skills once when I was in my 20s. The way he watched me do it and smiled with approval was one of the creepiest yet funniest things I've ever seen. Think Grinch-scheming face."
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15points
#36
"There’s this cute little coffee shop in my town that I absolutely love to go to. I’ve known for a while that it’s run by a Jewish cult called the Twelve Tribes (they’ve tried to recruit me and invite me to their sabbaths and stuff). I invited a guy I met in college there on a date.
He was nice, and it went well. I eventually told him about this, and he started telling me what tribe he was from (I guess it’s a biblical thing? Idk, I practice witchcraft and have most of my life). He then started talking to the barista about it VERY intently and getting information about the sabbath and stuff. As we were leaving he was very insistent that we go to one together.
I don't know, I think I may have gotten this man into a cult or he was already part of it. Not sure, didn’t go on another date."
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14points
#37
"Our to dinner, he’s wearing white jeans (early ’90s) and doesn’t realize he’s stuck the whole side of his hand in bbq sauce. Rubs his hand down his leg and he’s got this huge greasy stain running down. Excuses himself to go to the bathroom to try to clean it, smeared it more plus it looks like he’s peed his pants. Brings me home, leans in for the kiss and hits some center console button for the rear hatch of his car, sets off an alarm, and can’t get it to stop. At that point, he tucked his tail and went home. Never heard from him again."
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12points
