54 Of The Funniest and Wildest Dating Stories Out There

Author image for Kim Cohen
Kim Cohen
Feb 19, 2023 4:00 PM EST

When you are single and dating, you often find yourself thinking that you've 'heard it all before.' You and your gal pals have had all the weirdest, funniest and strangest dates in the world and nothing else comes close.

That's until we came across a little, unknown Instagram account that has some of the funniest and wildest dating story snippets you'll ever read in your life, and you'll start realizing that maybe your own dating life could actually always be worse.

From escaping with lame excuses of going to the bathroom, to your date's mom being sat behind you at the movies, and everything in between - these dating stories will have you laughing, crying, cringing and might actually make you feel a whole lot better about your own dating life.

Get ready to be amazed with some of these stories because just when you thought nothing else will be able to surprise you in the world of modern dating...we found this. 

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  • 01
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory My last date was a socially distanced walk whereby he told me the reason his marriage had ended was because he had had an affair... With his wife's mother!! Nathalie
    via The dating stories
  • 02
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory My date took me to a very nice restaurant. Our waitress leaned into me and whispered: "You're the third one this week." Deb
    via The dating stories
  • 03
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He told me he wanted to take me to one of his favourite places so I dressed up. It was a lingerie store. Ciara
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  • 04
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He had a starter, a €35 steak and lots of drinks. I had a €12 salad. He insisted we split the bill 50/50. Anastasia
    via The dating stories
  • 05
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory On our second date he pulled out a box of brown hair dye as a gift as he didn't like my hair colour. Dominique
    via The dating stories
  • 06
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We went to the movies. He took a used bag of popcorn out of the bin and went to get his "free refill". Anne
    via The dating stories
  • 07
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory In the middle of our date he got a phone call from his ex and they decided to get back together. We had to awkwardly sit through the rest of the meal. Beth
    via The dating stories
  • 08
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - On my first date with Rob, after a few drinks and a nice meal, he asked me if I would go with him as he "wanted to introduce me to someone". A bit hesitant, I followed him as he walked into a cemetery. Kneeling down in front of a thumbstone, he said "Mum, I'd like you to meet Jenny, she'll be my wife one day". Jenny
    via The dating stories
  • 09
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He brought a plastic bag to puke in because "he gets nervous on first dates". He used it. Francesca
    via The dating stories
  • 10
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I agreed to meet his guy in a coffee bar for a date. I arrived and he was sat with his 3 kids (that I had no clue he had). I bought them all a milkshake and politely left shortly after. Tina
    via The dating stories
  • 11
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory On our first date, 10 minutes into the conversation, I told my date I worked at Google. He then spent the rest of the evening trying to convince me he deserved a job as Google was his dream company. Rachel
    via The dating stories
  • 12
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory On our first date, John spoke for hours about his divorce, how his ex made his life miserable, and the custody court case he had coming up. I couldn't get a word in. I messaged him the next day to let him know I didn't feel a connection after which he proceeded to ask me if I felt like accompanying him to court for moral support the next day. Leah
    via The dating stories
  • 13
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I had a few too many drinks before a Tinder date. Spotting him from afar, | sat down at his table. He said he wasn't my Tinder date but I kept insisting and we argued. Things got really awkward when his girlfriend returned from the loo. My real date at another table had recognised me and witnessed the whole scene! Annette
    via The dating stories
  • 14
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I accompanied my best friend to a speed dating event for single business. people. We had a good time except for one guy who was drunk and really obnoxious. I literally told him to F off and leave us alone. Come Monday, I visited a client in the CBD and found myself eye to eye with him in the elevator. Charlie
    via The dating stories
  • 15
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I was so nervous and excited to go on this date. In the process of getting ready, I put on two different boots so I could pick which one looked best. The whole night I felt like people were looking at me. It was only when I got home I realised I was wearing two different coloured shoes. Alexia
    via The dating stories
  • 16
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We organised to meet for a few drinks in a cool bar. He arrived 15 min early and messaged me to ask if he should order a bottle for the two of us and what type of wine I was into. I thought "How considerate, we're off to a good start", only to find him 15 min later plastered with an empty bottle of rosé in front of him. Ruth
    via The dating stories
  • 17
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We decided to meet for a walk in the park closeby to where we both lived. I was pleasantly suprised to find out he'd organised a cheese and wine platter, brought a picnic blanket and cushions to sit on. He then persisted I should take him home and we should have sex 'as a thank you for all the effort he'd put into it'. Urgh. Helen
    via The dating stories
  • 18
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I was on a date with a guy who got so drunk I told him I was going to the bathroom and instead got a taxi home. 20 minutes later, he called and asked if I was ok because I had been in the bathroom for a while. I replied, "Oh, you thought I meant the bathroom at the bar? I meant the one in my apartment." Erin
    via The dating stories
  • 19
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I'd had a few drinks. We were sitting across from each other. I fumbled around in my handbag to find my lip gloss. I pulled it out and up to my mouth, only to discover it was a tampon. Hannah
    via The dating stories
  • 20
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory My date arrived 30 min late at the bar we were meeting that night. He then told me he had trouble finding something to wear the cat hadn't peed on. Claire
    via The dating stories
  • 21
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We went to a park to walk around. He pointed to a ravine and said "jokingly" that he would probably hide my body there and no one would ever find it. Peta
    via The dating stories
  • 22
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He decided to kiss me (terribly) mid sentence while I was talking about my brother being in the hospital. Meredith
    via The dating stories
  • 23
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We were walking to the park, I was freezing and had no jacket on, he did. I asked him if he could grab my jacket from my backpack after which he said "OMG, you are so smart"! Then he proceeded to get it and put it on himself. Eva
    via The dating stories
  • 24
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory A guy I had been on two dates with asked if I wanted to go to a basketball game. When we got to the court I realised he took me to his little brother's match. We sat with his parents and I had to make awkward conversation. After the game, his brother asked if I was his girlfriend. He answered, 'Yes' at the exact moment I answered 'No.' That was our last date. Sonia
    via The dating stories
  • 25
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He showed up with his twin brother and asked if I'd be cool with dating both of them because they share everything. Elien
    via The dating stories
  • 26
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I dated a guy for 3 dates before noticing he only had one hand. Jules
    via The dating stories
  • 27
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I had a bit too much to drink on our first date. We were sitting in one of the booths at a bar. When I came back from the bathroom I sat down in the wrong booth. Took me a minute to realise it was a different person. Marie
    via The dating stories
  • 28
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I went on a coffee date with this guy. Our date lasted for three hours, just laughing, talking and sipping coffee. The next day he texted me and asked if I wanted to be exclusive with him. Ruth
    via The dating stories
  • 29
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory My date went to the bathroom. The guy sitting next to us looked at me and said "my date isn't going as well as I hoped, would you be free to hang out later?" Carol
    via The dating stories
  • 30
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory A guy I had been dating showed up at my house unannounced at 9.30 pm. I was flabbergasted and told him this was not really a visit I was waiting for but since he drove 1h especially to see me, I kinda felt obliged to let him in. He asked to use the bathroom, came back naked and went to sit on his knees in front of me. Cindy
    via The dating stories
  • 31
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I got to our date location early and felt like there was something in my nose, so I started picking it. Next thing I knew, there was someone parked next to me. It was my date. Vincianne
    via The dating stories
  • 32
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory One time, a guy took me to the movies. I noticed that during the movie, he kept looking at the person behind him. Turns out, his MUM was sitting behind us the entire time! Samantha
    via The dating stories
  • 33
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I was waiting for my date at a wine bar. The waiter came up and asked me if I wanted something to drink, so I ordered some wine. He brought me the wine and sat down next to me. I was really confused until he said "I'm your date, I just finished my shift". Caitlin
    via The dating stories
  • 34
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory At the end of our date I asked him if he felt like catching up again. He told me I shouldn't take it personal but he was going to take a break from dating. FML Margot
    via The dating stories
  • 35
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory My date took me to a steakhouse and told me he doesn't drink because he thinks alcohol is for people who aren't intelligent. This is after I had two drinks. Bree
    via The dating stories
  • 36
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We went to karaoke and he sang "I will always love you" by Whitney Houston. It was a beautiful performance. He then proceeded telling the whole crowd "This song was for my ex." Patty
    via The dating stories
  • 37
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He texted me he was deciding between a first date with me or getting a free dinner from his friend for helping him move. Sie
    via The dating stories
  • 38
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We went for dinner on our second date. I left cash for the tip. He picked it up and pocketed it. Mia
    via The dating stories
  • 39
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory His family owned a funeral home. I didn't have any issues with that, but he spent the later part of our dinner telling me what kind of makeup techniques he would use on me if I died. Isabelle
    via The dating stories
  • 40
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory On our second date he offered me to drive me back home. He used a lint roller on my shirt and pants before he would let me in his car... Julie
    via The dating stories
  • 41
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I went on a date with a guy that couldn't stop complaining about his ex. He then started to cry and told me I reminded him of her. Mila
    via The dating stories
  • 42
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory My date picked a meat restaurant for dinner, ordered a large bowl of BBQ sauce and ate it with a spoon... like soup. Mona
    via The dating stories
  • 43
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He pretended to have misplaced his wallet, asked me for some money to catch a cab home after I already paid the bill. He then unmatched me and blocked my number. Anne-Marie
    via The dating stories
  • 44
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory On our second date we went to a comedy show. During the intermission, he opened his Tinder app and started swiping while I was sitting right next to him. Kristin
    via The dating stories
  • 45
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He showed up an hour late, drove to a park and said "I have a condom". Lisa
    via The dating stories
  • 46
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory We stopped by his family's BBQ on the way to our date and found out we were third cousins. Kristy
    via The dating stories
  • 47
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He took me to a fancy restaurant and ordered and ate the most expensive food on the menu. He then went to the bathroom to wash his hands and never returned. Elisa
    via The dating stories
  • 48
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He asked me about my German heritage, explaining how he wanted to make sure he would have blonde- haired, blue-eyed Aryan children. Britt
    via The dating stories
  • 49
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory 147 hours. That's how long we chatted before he decided he didn't feel a connection. Mel
    via The dating stories
  • 50
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory 20 minutes into our first date, he Facetimed his 3 kids (which I had no idea he had), turned the camera to me without any warning and introduced me as "dad's new friend". Elle
    via The dating stories
  • 51
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory He knelt on the floor and told me he loved me right in the middle of the underwear section of a department store. Vicky
    via The dating stories
  • 52
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory After my second date with a guy I met at the pub, he took me back to his house where I didn't realise he still lived with his parents. He then proceeded to show me his room or more specifically, his extensive alphabetised porn collection. Claire
    via The dating stories
  • 53
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory From your photo, he said, I thought you were too good for me. I'm glad to see you've got flaws. Then he started listing them... Stephanie
    via The dating stories
  • 54
    54 Of The Funniest and Wildest Dating Stories Out There | Thumbnail includes true story dates text - Font - #truestory I once took a girl to Starbucks because I forgot her name. Ben
    via The dating stories

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