We’ve all had our fair share of terrible dates, but some people have really special dates. Fortunately, they have a safe place to discuss these vivid experiences—which can range from embarrassing to downright terrifying—on the Internet.
While we’re having dinner, I muster up the courage to ask him to take off his headphones. He says, “Don’t be afraid! With pride and complete confidence!” with certainty. I am completely focused on you.
This is a camera, not a phone headset.
“Can I start your drink?” was the typical greeting the waitress gave us when she approached us in the restaurant.
After ordering drinks and water, I turned to face my companion and remarked, “And whatever she’s getting.” Then my date turned to face me, looked at the waitress, and then looked at me with a confused expression. I asked if she was okay or if she needed more time to look. After she cleared her throat, my date asked if I knew the waiter. I asked why and I said no. The date then got very angry and asked why the waitress was talking to me and staring at 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.
We’re going on our first date to this new pizzeria in town. He orders me to get out of the car first. When she sees me, she giggles and asks, “Is that your little car?”
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. She asked me where I was going and I left in the middle of our meal.
One night, while bartending at a small music venue during a concert, I got a call from a woman who insisted on giving me my number. We didn’t recognize the name or the description, but after a few nights of talking, we made plans to meet.
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 didn’t call me. However, I decided to be polite and give one date a chance. Sometime during the evening, we started exchanging phone photos. “This is my dog,” “This is my son,” “That’s me in Vegas,” and so on.
Bonnie then gave me a picture that said, “This is me with my best friend Sarah.” Sarah looked extremely familiar when I looked over. I remember talking to Sarah and giving her my number because she was my type. 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. Personally, her best friend Sarah cheated on me on behalf of her boyfriend. I went out.
On our first date, we decided to go out to dinner. After ten minutes she tells me that because “that’s what a real man would do” she wants me to pay for her food and takeout orders for her two closest friends. Seemed like I was fine with it, told her I had to get the card from the car and left.
I went on my first date with a girl who insisted on taking me to this fancy restaurant where she ordered a $45 steak, a $15 cocktail, and a $25 appetizer. 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 would be wonderful,” I exclaimed. So I did it.
We were great friends, but I had a huge crush on this lady from college who I had known for almost 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.
This was a friend’s experience. Environment: He has a beard. You know you have to shave it if it’s going to work, right? A girl says this to my friend when they go to dinner. He simply turned and walked her back home without saying anything.
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.
I went on a date in college with a lady who threw an empty soda can out of her car window and rolled down the window. I walked home after telling her to drop me off at the next traffic light.
He invited a bunch of people I’d never met to play dodgeball with me and a friend. He spends more time with his friends than with me, but that’s ok because I have my friend who keeps me busy and we have a decent time. 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. Then this fellow loudly shouts, “Wham, boom, right into the clam!”
I immediately turn to my friend and ask her if she is ready to go. I say goodbye to him and his friends. came home to a barrage of texts criticizing my “immature” behavior.
We met in front of one of my favorite restaurants.
She shook my hand, barely looked up, and continued typing on her phone. As she continues to type messages on her phone, we sit down. So I asked her the typical dating questions and after three attempts to start a conversation I ended up getting a “yes” and finally a “wait a minute.” I thought something terrible might have happened after the “wait a minute”. comment so I asked if everything was ok. Her friends are her top priority, she snapped. I was a bit surprised. Then, when our waitress is about to greet us, she interrupts with a grumpy “Finally!” then he goes back to the phone after growling very nasty at her about the drink order.
After about a minute of silence, I said, “Excuse me,” asked for some water, and stood up. I found a waitress, thanked her, said I was leaving and left. The fastest date of my life. All this in a maximum of ten to fifteen minutes. I have never met someone so rude on a date in my entire life. I convinced myself that all my terrible dates were in one. We can only hope so!
I went to pick a date who was blind. “Ew,” she mumbled as she opened the door and turned to me. “Yeah, I agree,” I replied, turning on my heel as I walked away from her. Not even five minutes had passed during the date.
I don’t treat the first date with anything fancy.
My favorite is to walk around the lily pad public garden and then go around the corner to play miniature golf. Sometimes I’ll do something else, like visit a planetarium or a museum, depending on the interests listed in her profile.
We clicked right away when I met this amazing girl. Our first date was at the local museum’s South American exhibit, which I assumed she would adore based on her profile. After that, we had banana chips and I felt like we had a decent date. I couldn’t wait to see her again.
After about three weeks, we succeeded. She had some work stuff and I had some work stuff. She was thirty minutes late, so instead of seeing a movie and going to a little restaurant, we just went out to eat. She talked negatively about the “last guy” she dated for ten minutes and took her to a pointless museum before taking her on a banana split. Her last date was too cheap, she grumbled, to buy dinner “like a real man.” She continued to speak without stopping.
I paid for the drink and half the appetizer excused myself from the table, and left. I blocked her on my phone and the app.
If you’re wondering how she didn’t know I was the “last guy” it’s because I shaved off my 10-day beard for the interview and she was staring at her phone most of the time.
Whether you’re single or in a committed relationship, dating is a never-ending roller coaster. Your significant other has the ability to surprise you with something completely unexpected, be it a happy surprise or an unpleasant one, even after you’ve been dating for a long time.
Navigating the dating world can sometimes feel like walking through a minefield, with every step holding the potential for both wonderful surprises and cringe-worthy moments. The stories shared by these individuals serve as a reminder that while some dates can be incredibly awkward, uncomfortable, or downright bizarre, they also highlight the resilience and humor that many of us can find in such situations.
From outlandish behavior and outrageous demands to simple misunderstandings and the occasional outright rudeness, these stories remind us that dating is rarely a straight road. The common thread of all these experiences is the remarkable ability of people to endure and even laugh at the absurdity of it all.
Whether it’s dating someone who doesn’t appreciate the art of conversation or finding yourself in the middle of unexpected drama with someone’s best friend, each story underscores the importance of staying true to yourself and not settling for less than respect and kindness.
Ultimately, while we may not be able to predict every twist and turn in our dating journeys, we can certainly learn to appreciate the stories we gather along the way. And who knows? Perhaps the most memorable dates are the ones that teach us the most about what we really value in a partner and in life. So here’s to all the awkward moments, hilarious encounters, and lessons learned – may they lead us to our best stories yet. Keep your heart open, and your sense of humor intact, and remember: every bad date is just a stepping stone to a better one.