50 Short and Funny Dating Stories That Are Almost Too Weird to Be True
1. The Taco Purse Incident
He knocked a taco into my purse mid-joke. It had sour cream. He bought me another taco and a new purse. I said yes—to both.
2. The Wrong Amanda
Showed up for a blind date with Amanda… wrong Amanda. We laughed, ate dinner anyway. I dated the right one later. Awkward success.
3. The Honest Catfish
She said, “I’m not the girl in the pics, but I cook great lasagna.” It was true. I stayed. Catfished by flavor.
4. The Silent Car Ride
Neither of us talked. All night. Somehow, it worked. We’re now married. Still not big on words.
5. Love Over Pizza… Almost
She picked pineapple, anchovies, jalapeños. I judged her toppings. She ghosted me. Worth it for the pizza… almost.
6. The Goat Date
His goat came with us. Yes, a real goat. He said she was his “emotional support hooved friend.” I didn’t even finish my drink.
7. The Magic Trick
He pulled a coin from behind my ear. I pulled out my phone and Ubered home.
8. Car Karaoke Disaster
He belted out Total Eclipse of the Heart with tears in his eyes. I hadn’t even ordered my drink yet.
9. The Tinder Twin
Met her at a bar. Swore she looked familiar. Turns out I’d also matched with her twin—on the same app.
10. Emergency Exit
She fake sneezed, said “I have COVID,” and left. Most creative ghosting I’ve ever witnessed.
11. The Chicken Suit
He thought it was a costume party. It wasn’t. He stayed anyway. Confidence level: legendary.
12. Left on Read
We both sat staring at our phones for ten minutes. I texted “hi” to break the silence. She left. Technically still on read.
13. Dog Over Date
She brought her dog. He sat on my lap the whole time. Honestly, the dog and I had more chemistry.
14. Flash Flood First Date
We got stuck in a gas station for 3 hours due to rain. Played Uno. Still better than my last relationship.
15. The Sneaker Freak
He made me take off my shoes before getting in his car. Then complimented my socks. I didn’t know what to do with that.
16. Overdressed & Underdelivered
I showed up in a dress. He wore sweatpants with pizza stains. He said, “I’m comfortable with myself.” I wasn’t.
17. Fast Food Proposal
He jokingly proposed with a chicken nugget. I said yes. Then dipped it in BBQ sauce.
18. The Wrong Table
We sat at the wrong reservation. Ate someone else’s birthday cake. Still have no regrets.
19. Not Her Cat
Her bio said “cat lover.” I asked about her cat. She said, “Oh I just borrowed that for the photo.”
20. Name Game
I called him Jake. His name was Josh. He never corrected me. We dated for a month.
21. The Great Escape
She said “I left my oven on,” mid-date. She didn’t have an oven. Or a kitchen.
22. Unfiltered Honesty
He said, “You’re hotter than your pics.” I said, “You’re not.” The check came fast.
23. The Waiter’s Revenge
He was rude to the waiter. The waiter spilled water in his lap. I tipped double. And left—solo.
24. Movie Mix-Up
Thought we were seeing a rom-com. Ended up at a slasher film. We both screamed more than once. Great bonding, though.
25. Scent-sitive
He wore so much cologne I had to breathe through my sleeve. He called it “signature scent.” I called it “chemical warfare.”
26. Card Declined
He tried to impress me with a fancy dinner. Card got declined twice. I paid. He didn’t say thanks.
27. Stranger Things
He showed up and immediately said, “You don’t look like your aura.” I didn’t stay long enough to find out what mine was.
28. The Mom Tag-Along
His mom came. “Just to meet me.” She stayed for the full meal. And dessert.
29. Extra Baggage
She brought three purses. Said one was for snacks, one for self-defense, one was just vibes.
30. The PowerPoint
He literally brought a laptop and showed a PowerPoint about why he’s “boyfriend material.” I admired the commitment. Not the content.
31. The Juice Cleanse
She ordered hot water and lemon. That’s it. Talked for 40 minutes about toxins. I left and got tacos.
32. The Wrong Day
She thought it was Thursday. It was Tuesday. We had a good laugh—then both went home.
33. The Flexer
He kept flexing his biceps. Even when eating. Ever watched someone curl a breadstick?
34. ASMR Guy
He whispered everything. Said he had a YouTube ASMR channel. I said I was hard of hearing.
35. Haunted Date
She said she lives with a ghost. I thought she meant her roommate. She didn’t.
36. GPS Fail
He drove us to the wrong restaurant. Three times. GPS said “recalculating.” So did I.
37. The Juice Guy
He drank beet juice with every meal. Including sushi. His teeth were purple.
38. The Free Sample
He invited me out, then said, “We’ll just hit Costco for lunch.” We did. I had six samples and left hungry and confused.
39. Dad Joke Overload
He told 11 dad jokes before the food even arrived. I laughed at two. He kept going.
40. Speed Dater
He told me I was his third date that day. “Gotta keep options open,” he said. I helped him close one.
41. The Weather Talker
He only talked about the weather. I thought maybe he was a meteorologist. He wasn’t. Just awkward.
42. Wrong Car
I got into the wrong car after the date. Cried when I saw a stranger’s dog in the backseat. They offered me tissues.
43. The Interview
She had a clipboard. Took notes. Asked questions like “Where do you see us in five years?” I saw myself leaving.
44. Hot Sauce Hero
He brought his own hot sauce. Like… holstered on his belt. Called it “Dragon Juice.”
45. Foot Selfie
He took a selfie of our feet. Said it was a tradition. I checked the bill and checked out.
46. Reverse Catfish
He looked way better than his pics. I was too shocked to say anything smart. I spilled my drink instead.
47. Giant Teddy Bear
He brought a 3-foot teddy bear to the date. “For vibes,” he said. The bear got more hugs than he did.
48. One Word Answers
I asked questions. He replied: “Yeah.” “Cool.” “Nice.” I left. He texted: “Why’d you leave?” I replied: “Yeah.”
49. Fork in the Road
She refused to use a fork. Ate her pasta with chopsticks. Then with her hands. I was impressed… and scared.
50. Napkin Notes
He wrote me a poem on a napkin. Rhymed “you” with “zoo” and “snack” with “heart attack.” Honestly, a solid ending.
