Hilarious and Cringy Dating Tales: Laughing at the Awkward Moments

Funniest Dating Stories Success Stories

The Funniest Dating Stories You’ve Ever Heard

Dating can be a wild ride filled with unexpected twists and turns. Whether you’re swiping through dating apps or meeting people in person, there’s always the potential for something to go hilariously wrong. In this article, we’ll share some of the funniest dating stories we’ve ever heard.

Shocking party treat

I encountered a man on tinder and we got along. But then, on our date, he vanished for a moment and returned with a small bag that appeared to hold broken glass. It turns out he had brought crack cocaine! I refused his offer and quickly left the scene.

Butter knife bandit

This person recounted how they were out one night when a thief arrived wielding a butter knife. The thief threatened to stab them if they didn’t hand over their valuables. Fearing for their safety, they gave in and the criminal escaped with their possessions.

An unconventional setup

A mature colleague of mine had the audacity to set me up with her son. He asked if i’d be up for dinner and i, feeling obligated, obliged. To my shock and dismay, i found out he was still living with his mom. As i was trying to think of an excuse to leave, she abruptly suggested i have some privacy for intercourse. Needless to say, i thanked them for the meal, made up an excuse, and never looked the same at work around her ever again.

The worst evening out

«We had set out for a night of sushi, but he had to cut it short and return to his place. It turned out he was scared to use public bathrooms. I had to sit in his living room, listening to him groaning while he was attempting to go to the toilet. Then he realised he had run out of toilet paper, and sent me a text asking me to bring a roll from upstairs. The smell was unbearable. It was without a doubt the crummiest evening i had ever experienced.»

A valentine’s date to remember?

This story is one of those «you couldn’t make it up» moments. My friend had been seeing a guy and was really into him, so when valentine’s day came around he wanted to plan something special. He had a passion for astronomy, so he chose a great location and brought a telescope to show her the constellations. She was delighted! She put on something special and invited him in.

To her surprise, he undressed, got into bed and then said he couldn’t be with her anymore. He had taken all his clothes off to break up with her! He said it was his way of giving her a nice valentine’s date before ending things.

The er date

It was a night out at the bar that ended in a dramatic trip to the er. A guy i had just met took me to a chinese restaurant for dinner. We ordered a variety of dishes and sampled them all. Soon after, my face went bright red and i broke out in hives. In the car, my breathing became labored and i asked him to take me home. But before we reached my place, i went into anaphylactic shock and stopped breathing. It turned out i was allergic to almonds and didn’t know it, and we had ordered almond chicken. He drove me to the hospital, but when the doctors started to revive me, my shirt and bra got ripped off, and he saw my breasts! As soon as my roommates arrived, he took off and was never heard from again.

A cemetery expedition

I went on a double date with a pal and the man i was seeing thought it’d be a great idea to pay a visit to a graveyard. We strolled around and conversed, but when we returned to the vehicle, he realised he had dropped his keys. We all had to go around and over graves to search for them.

An over-sharer

The chap who requested me out worked at a garage but he didn’t take the time to clean up before the date, so he arrived completely covered in oil. The whole evening was horrible, but finally i gave up after he said, “do you ever hang out in hospitals? I’m attracted to blood.’ i’m not even making this stuff up.

This tinder disaster

This tinder misadventure is not one to be forgotten. Not only was the guy at the meet up not the same as his pictures, he had the nerve to tell the person he was meeting that they looked different than he expected, and then offered to give them money to leave!

The clumsy superman

This guy showed up to their date dressed as superman — white button up shirt over a blue superman t-shirt, clark kent hairstyle, glasses and all — and yet he still took her to a sushi restaurant despite knowing she was a vegetarian! He then proceeded to spill sake all over her, and to make matters worse, he pulled out his digital camera to show her pictures of his trip to europe with his mother five years ago. To top it all off, on the drive home he told her he wanted to have a relationship like leo and kate in titanic.

Date disaster stories

The forgetful dateAfter 3 hours of what was supposed to be a romantic date with a tinder guy, he bizarrely asked if i wanted to come see his neighbor’s new puppy. To crown the weirdness, he referred to me as «stacey»!

An educational dateMy date drove me to a restaurant, but to my surprise, he had a backpack with him. He asked for a table next to an outlet, and then opened his laptop to show me a powerpoint presentation about a pyramid scheme he was recruiting me for! He spent the entire date trying to get me to join!

A date that moved too quickly

I’d been interested in this person for a few weeks, and after exchanging a few flirty conversations, they finally asked me to go to a show with them. We had a great time, until suddenly their parents showed up! It turns out they had invited them to meet me — on our very first date!

A disastrous date at the lake

Things only got worse from there. We decided to go for a walk at the lake, and it just went downhill from there. We ended up having an argument, and i thought it was the end of that relationship.

A swim gone wrong

My college pal had set me up on a group date, and we all decided to go for a swimout on the lake. Austin, my date, was completely tanked by then. Suddenly, he got real still and we noticed he had a face like a constipated kiddo. His friend shouted, «get in the boat, now!» and soon after, a huge poop bobbed up close to austin. He laughed and acted as if nothing happened.

Awkward dinner chat

I went out on a date with a female colleague in the same line of work. She revealed that she was aware of my boss, but then went on to say how attractive they were. I had to keep quiet, as i was employed by my mum’s organization — so my date was, in fact, talking about my mother the whole time!

Valentine’s day indigestion

It was valentine’s day and i was feeling a bit queasy. Unfortunately, my date hadn’t eaten properly either — and we ended up throwing up together!

Once upon a time in secondary school

I recall the time i was asked out on valentine’s day with a whole mess of gifts, a big teddy bear, and a huge bouquet of roses. Alas, on that morning i had a bout of nausea and ended up vomiting all over the poor guy and his offerings. Yikes!

This bbq without clothes on

I met someone on tinder and went to their home for a bbq. This person got really high and then proceeded to streak around their backyard. I promptly left and never spoke to them again.

The Stalker

Jessica started chatting with a man online who seemed sweet and charming. They hit it off right away and exchanged numbers. But after a few days, she started receiving hundreds of texts and calls from him, even when she told him she was busy or didn’t want to talk. She eventually had to block him and report him to the dating site.

The Secret Life

Rachel went out with a man she had met online a few times and felt like things were going well. But one day, she received a message from his wife on social media. She was shocked to find out that he was married and had been living a double life. Rachel immediately ended things with him and felt betrayed.

The Criminal

Carla went out with a man she had been talking to online for a few weeks. He seemed nice and charming, but she started to get a bad feeling about him when he suggested they go to a secluded area for their date. She declined and later found out that he had a criminal record for assault. She was thankful that she had listened to her instincts and had stayed safe.

The Scammer

Julie met a man online who claimed to be a successful businessman. They went out a few times, and he even took her on a weekend getaway. But one day, he suddenly disappeared and stopped responding to her messages. Julie later found out that he had scammed her and several other women out of thousands of dollars. She was devastated and learned to be more cautious when dating online.


No matter how awkward or uncomfortable a date may seem, it always makes for a good story. These funny dating stories prove that even the most cringeworthy moments can be turned into something hilarious. So the next time you find yourself in a bizarre situation while dating, remember that it’s all just part of the journey. Who knows? It might make for a great story to tell your friends later.


I am Dr. Emily Kim, a 35-year-old family psychologist. I grew up in a small town in the Midwest and obtained my undergraduate degree in psychology from the University of Michigan. I then went on to earn a Ph.D. in family psychology from Northwestern University.

After completing my studies, I began working as a family psychologist, specializing in helping couples and families navigate the challenges of their relationships. Over the years, I have developed a reputation for my empathetic and effective approach to therapy.

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