These anecdotes offer a glimpse into the unpredictable world of dating, where encounters can range from awkward to downright bizarre. Each story captures a moment of discomfort or disbelief and shows the variety of experiences people can have when meeting new romantic prospects. Despite the inherent vulnerability of getting there, these individuals bravely share their stories, finding comfort and even humor in the aftermath of their less-than-ideal dates.
In the first story, friendship is tested when romantic feelings are revealed, leading to a brutally honest conversation that ends with wounded pride and dashed hopes. The experience highlights the delicate balance between friendship and romantic attraction and shows how easily dynamics can change when emotions come into play.
Everyone has had a terrible date, but some people have the most memorable experiences. From weird exchanges to downright creepy behavior, these dates went so wrong that these people had to end them as soon as they had the chance.
Fortunately, social media gives individuals the confidence to share these embarrassing experiences without fear of being judged.
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.
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.
He invited some people I’d never met to play dodgeball with me and a friend. He spends more time with his friends than with us, but that’s okay because I have my friend to keep me busy. We’re having a good 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. “Wham, boom, right into the clam!” this person exclaims at that moment.
I immediately turn to my friend and ask 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” | he played
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.
We had a date outside 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. After three attempts to start a conversation, I finally got a “wait a minute” and a “yes” when I asked the typical dating questions. I asked about the status of things because I thought something negative might have happened in response to the “hold on a minute” comment. Her friends are her top priority, she snapped.
I was somewhat surprised. Then our waitress arrives, interrupting her with a sour “Finally!” Then he yells a drink order at her as rudely as possible and goes back to the phone.
After saying “Excuse me” and asking for water, I got up after about a minute. I found the waiter, gave her a chance and said I was sorry and I was leaving. 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!
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 to her house without saying anything.
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. While we’re having dinner, I muster up the courage to ask him to take off his headphones.
He speaks with pride and complete confidence, saying, “Don’t be afraid! I’m totally focused on you.
This is a camera, not a headset with a phone.”
The waiter came to greet us and offered us the usual “welcome…can I start you off with a drink?” 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.
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.
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.
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. 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.
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.
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 new, like visit a planetarium or a museum, depending on what she’s interested in on her profile.
I met this amazing girl and we clicked right away.
Our first date was to the local museum’s South American exhibit, which I assumed she would adore based on her profile.
After we ordered banana splits, I felt like we had a pretty good 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 we decided to just go out to eat instead of seeing a movie and having dinner at a small restaurant. She talked negatively about the “last guy” she dated for ten minutes, took her to a stupid museum, and then to a banana split. She grumbled that her last date cost too little for him to buy her 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.
I shaved off my 10-day beard for the interview and she was focused on her phone most of the time, so maybe that explains how she didn’t know the “last guy” was me.
These reports of catastrophic data serve as cautionary tales to remind us of the unpredictable nature of human interactions. From awkward conversations to bizarre behavior, these experiences highlight the importance of communication and mutual respect when dating. Clearly, while social media provides a platform for sharing such anecdotes, the real-world consequences of these encounters can be emotionally demanding and sometimes even hurtful.
Despite the discomfort and disappointment these individuals faced, their stories also demonstrate resilience and self-respect. Walking on a date, while unconventional, can be an act of self-preservation and empowerment. It is a decision to prioritize one’s own well-being and dignity, even in the face of awkwardness or rudeness.
Additionally, these stories underscore the need for honesty and authenticity in dating. Pretense and deception, whether intentional or not, only serve to complicate relationships and breed mistrust. Transparency and open communication are essential to building real connections and fostering mutual understanding.
Ultimately, while these stories may elicit laughter or sympathy, they also offer valuable lessons about setting boundaries, trusting instincts, and prioritizing self-esteem when seeking romantic relationships. As we navigate the complexities of dating, let these anecdotes remind us to approach each encounter with empathy, integrity, and a healthy dose of humor.