Dating can be an exciting journey filled with the promise of new relationships and shared experiences, but it can also unexpectedly turn into embarrassing and unforgettable mishaps. While the ideal date can lead to a beautiful evening and possibly a future together, the reality is often less predictable. From bizarre behavior to a complete mismatch in personality or expectations, the stories of failed dates are as varied as they are entertaining.
Stories shared from personal experiences highlight a range of disappointments to downright bizarre dating escapades. These stories reveal the unpredictable nature of meeting new people, whether it’s a simple case of misbehavior like littering or being glued to your phone, or a more peculiar situation like finding a collection of toenail clippings. Even when set up with good intentions, meetings can quickly go south and lead one or both parties to walk away quickly.
Social media has become a treasure trove of such stories, providing a platform to share and empathize with dating disasters without fear of judgment. This collective sharing not only serves as a form of catharsis but also helps others feel less alone in their own dating struggles. Each account, while unique, underscores the commonalities of finding connection in the modern age and the resilience that is often needed to navigate it.
Everyone has had a bad date, but some people have particularly memorable stories. From strange interactions to downright unnerving behavior, these dates went so badly that the people involved had no choice but to quit early.
Fortunately, social media provides a forum to share these embarrassing moments without fear of being judged. Also, don’t forget to check out our bonus area for a story with a truly unpredictable ending.
When we went on a date in college, a girl rolled down her car window and threw an empty Coke can out the window. It was completely uninteresting. I walked home after telling her to drop me off at the next traffic light. © Reddit/HerrowPries
On my first date, I went to a fancy restaurant where the girl insisted on paying $25 for an appetizer, $45 for a steak, and $15 for a drink. She refused to put down the phone and continued to receive texts and receive calls. The waitress spotted me and motioned to me from behind. After I left, the waitress asked if I would like to pay for my portion and leave it on the table. She had separate accounts that were all exposed. “That’d be amazing!” I shouted. So I did it. © Reddit / ELPwork
We were the best of friends, but I had a crush on this lady from college for about two years. I asked her out—to be honest, we had coffee together.
While we were talking she started telling me about all the guys she slept with. I don’t mind because I was dating at the time, but I wouldn’t tell her about it either. Still, she went on to explain that if we started dating, I would most likely be the ugliest guy she’d ever dated, and she’d be embarrassed if people got the wrong impression about us at times.
I was on the verge of tears. We were the closest of friends and she wasn’t typically like that, so the fact that I liked her so much really hurt my pride. I told her how I felt and turned to leave. © Reddit / iamnotalways***
he went to the man to meet him for the first time. His coffee table was covered in a pile of toenail clippings. Not just one recent clipping. There were a lot of clippings. I walked out the door. © Reddit/Amos_Moses83
One night while I was bartending at a small music venue during a show, a woman called and demanded I give her my number. We didn’t recognize the name or the description, but after a few nights of talking, we made plans to meet up. I’ll call her Bonnie. We met at her neighborhood tavern. Even though Bonnie didn’t look very familiar, I wouldn’t give her my phone number. She was definitely not my type. However, I decided to be polite and give one date a chance. Sometime during the evening, we started exchanging phone photos. “Here’s my dog”, “Here’s my son”, “Here’s me in Vegas” and so on. Then Bonnie pulled out a picture and said, “This is me with my best friend Sarah.” Sarah looked extremely familiar when I looked over. Sarah really matched my personality and I vividly remember exchanging phone numbers with her. Then it dawned on me that the night I was giving out my number at work, Bonnie was the woman who had been standing up for Sarah the whole time, quietly going about her business. Basically, Sarah, her closest friend, physically cheated on me on behalf of her boyfriend. I went out. © Reddit / t480
We’re going on our first date to this new pizzeria in town. He orders me to get out of the car first.
Then he notices me and asks, “Is that your little car?” with a giggle.
While we’re waiting to make our own pizza, he pulls out his phone and clearly blocks me on Snap and Tinder while we’re still in line. As I was leaving in the middle of our dinner, she asked me where I was going. © Reddit / mattjwx
This was a friend’s experience. Environment: He has a beard. He says, “You do realize that if it’s going to work, you have to shave it off, right?” as my friend picks her up and they go to dinner. He simply turned and walked her back home without saying anything. © Reddit/Jeborisboi
He invited some people I’d never met to play dodgeball with me and a friend. We have a good time, but he seems to spend more time with his friends. But that’s okay because I have a friend of mine who keeps me busy. We’re hanging out in the parking lot before the first game starts when he suddenly grabs a ball and throws it in my crotch.
“Wham, boom, right into the clam!” this person exclaims at that moment. I immediately turn to my friend and ask her if she is ready to go. I say goodbye to him and his friends. Immediately arrive home to a flood of texts criticizing how “immature” | played © Reddit / Monpetitvulcan616
We had great internet chats and agreed to meet up.
His Bluetooth headset has a small LED light to indicate when it’s on. He wears it while drinking. When we’re at dinner, I muster up the courage to ask him to take off his headphones.
Speaking with pride and complete confidence, she says, “Don’t worry! I’m completely focused on you. This is a camera, not a phone headset.” © Reddit/anarchypretzel
I went to pick a date who was blind. After opening the door she looked at me and let out an “Ew.” “Yeah, I agree,” I mumbled, looking at her before pirouetting away. Not even five minutes had passed during the date. © Reddit/Outlander56
At the restaurant, a waitress approached us and said, “Welcome…can I start you off with a drink?” as usual. After ordering drinks and water, I turned to face my companion and remarked, “And whatever she’s getting.” My date then turned to me, looked at the waitress, and then looked at me with a puzzled expression. I asked if she was okay or if she needed more time to look.
Then my date asked me if I knew the waiter after she cleared her throat. I asked why and he said no. The date then became very irrational and wanted to know why the waitress was staring at me and talking to me when she should have been talking to her alone. I was taken aback and thought, “What?” She goes on to say that I should let her know right away if we have problems with the waitress. At that point, I turned to face the waitress, told her to cancel my drink order, apologized, and stood up to leave.
When I went to the car I blocked the date number and everything. © Reddit/Capitalkid
We met this girl through a dating app. Her profile was quite beautiful. After a two-week conversation, we met for coffee. Even then she was breathtakingly beautiful. However, she immediately told the woman who made her coffee, “That stupid barista misspelled my name.” Still, I decided to sit down.
In the first ten minutes, she disparaged the coffee shop, the barista, her sister-in-law, her new nephew, and her ex-lover.
She subsequently became “jealous” when the barista smiled and took my coffee order. I told her I wasn’t interested and thanked her for her time. After paying for our coffees and tipping the barista generously, I left. © Reddit/Weak_Dog7271
Bonus: An Interrupted Date.
She was rude, ignored me, and ended up spilling my entire glass of ice water on my lap. At that point, we hadn’t even received our lunch yet so I told the waitress to pack it up for me as I was leaving. It was more than I could take. Especially after driving to the restaurant, I had had enough. Next time I will go on a date with my husband alone. I’ll leave the toddler with Grandma. Children, occasionally. © Reddit/sauerpatchkid
Whether you’re single or in a committed relationship, dating is never an easy task. These heart-wrenching tales of romantic attempts gone awry serve as a sobering reminder of how fickle love and relationships can be. Hurt!
The anecdotes shared above serve as humorous and sometimes cringe-worthy reminders of the unpredictable nature of dating. From downright rude behavior to bizarre incidents, these stories reflect the wide range of experiences individuals encounter in their search for connection. Social media has provided a platform for people to share these moments, turning what could have been private embarrassments into shared stories of dating disasters. While each account differs in its specifics, the common theme is the universal challenge of navigating the complex world of romantic relationships. These stories not only offer a chance to laugh and maybe cringe in solidarity, but they also remind us of the importance of respect and communication when dating. Ultimately, whether a date leads to a story of horror or humor, each is a lesson in what we do and don’t want in a partner.