20 Men Who Went on Dates They’ll Remember Until Old Age

Some men believe that shaving and bringing a gorgeous bouquet are enough for a perfect date. But that doesn’t mean that the date will go according to plan. Heroes of this article told about their dates that went wrong.

Story1
I met a girl online. She seemed really sweet, so I asked her out to dinner. We were sitting there when she asked, “How many girls have you been with before me?” I tried to joke and said, “155.”
Out of nowhere, she jumped up and started yelling at the top of her lungs, making a scene. She even demanded they call the police. Luckily, security stepped in and escorted her out.
The waitstaff felt sorry for me and even suggested that I stay and eat, but I was so embarrassed I just ran out. © Luckytxn_1959 / Reddit

Story2
I went on an ice cream date with a girl once. It was going pretty well, then she abruptly got up and said, “I need to go.” 20 minutes later, I get a text saying she was lactose intolerant and that she wanted to try again later that night. © Ben1313 / Reddit

Story3
Went on a date with a girl I had a crush on. We went to some festival or other, but what I remember is that we met her boyfriend at one of the stalls. And she actually wanted to bring him along for our date. Girl never mentioned even being in a relationship. © zheb*r / Reddit

Story4
We were out to dinner and everything was normal. This was date one, by the way. She had a big bag, but women always have large purses, so I didn’t think anything of it.
Well, my buddy is our waiter and midway through him telling us about the specials we hear a meow. Or, at least, we think we do. He and I kind of look at each other like, “Did you hear that?”
Anyway, he continues with his pitch and about 10 seconds later there’s a very audible drawn out meow. I go, “Okay, there is definitely a cat in this restaurant!” I look across at her, and she’s staring at me all wide-eyed and with a completely straight face says, “I swear I’m not a crazy cat lady.” Then reaches down and opens her bag and a cat jumps into her lap.
My first reaction was, “This date’s over.” But, it turned out she had been through something pretty traumatic recently and had gotten a kitten that was really helping her, and she was so nervous for our date she wanted him there. His name is Higgins. He’s almost 16 and is in this room with me right now. © Unknown author / Reddit

Story5
A friend of mine met a girl who set up a double date and decided to bring along her friend. My friend begged me to come, and even though I wasn’t really keen, I agreed.
The girl who was supposed to go with me acted really haughty toward the waitress (who was gorgeous). I immediately made it clear that I don’t tolerate rudeness and that every job deserves respect.
After dinner, my friend and his date left for a jazz concert, and “my” girl invited me to her place. I politely declined and went to the restroom, waited 7 minutes so she could leave without losing face.
But she caught me at the exit: “Ah, so you decided to ask that waitress out! I’ll make sure she gets fired — she’s stealing my date!” I was completely stunned. © Cannotakema / Reddit

Story6
I wanted to date a girl from work. We went to the movies and a café. I walked her home and gave her flowers and chocolates. It seemed like we liked each other.
Then I texted her, “Any plans for tonight?” After her reply, I nearly froze. She said, “My personal life is none of your business!”
I was completely stunned. I just sat there thinking, “Uh… what was that about?” I decided not to push it and stay away from her after that. © KaramazovDF / Pikabu

Story7
Went on a date to a movie with a girl when I was a teen. She spent the whole movie just whispering my own name into my ear, as if it were sexy or something. We did not date for very long. © EmeraldJonah / Reddit

Story8
I was going on a date and brought a bouquet with me. She didn’t show up, so I called, and she said she’d changed her mind. Well, I wasn’t about to let the flowers go to waste!
I walked down the street, giving flowers to girls I passed, smiling and wishing them a great day. They smiled back — some shyly, some happily, some joyfully. I returned home in a fantastic mood. © Overheard / Ideer

Story9
There was a funny situation on a first date. An interesting woman was telling me about her 7 kids. I also found out she’s a vet and loves neutering cats. I realized she was joking, but I honestly confessed that hearing all that made me feel a little uneasy.
So, I suggested we wrap up the date. Maybe she didn’t like me and was trying to brush me off in her own way. © Mikhail / ADME

Story10
I went on a date with a girl. We walked around and talked, then stopped by a café. She told me about her exes, who never gave up their bad habits.
In the end, she told me I was too good for her, that she liked bad boys, and walked off. I was left standing there in shock. © Shtolz Croicz / ADME

Story11
We had pizza sitting on the floor, surrounded by her pet pigeons. No, not the cute doves. She had a bunch of those rats from the skies that swarm cities.
She finds them hurt and takes them in to care for them. It was not a bad kind of weird. © LoanedPurr / Reddit

Story12
I went out on a first date with a girl about 25 years ago. I went and purchased new jeans, new shirt, shoes, got a hair cut. We went out for sushi, and we had a nice time. Afterwards, we decided to go to a bar she liked and listen to some music.
We get to the bar, and we get seats and I order drinks from the bartender, and continue chatting up my date. I noticed that she had become very quiet… sort of intense. I keep yapping away, when the bartender returns and slams our drinks in front of us with such intensity, half my drink sloshed out of the glass onto the bar.
My date says, “You’re a jerk,” to the bartender.
Bartender: “You’re a tramp.”
My jaw dropped and I said, “Hey! What the heck?”
Bartender says, “I’m her boyfriend.”
Date: “Were my boyfriend.”
I realized I was being used to piss off her ex. I said I needed to use the restroom, and excused myself. I left. About 10 years ago, I saw their wedding announcement in the paper. © LostinLies1 / Reddit

Story13
On the second date with my future wife, I brought cables for the record player she had, along with some records. I connected the cables to the speaker, we played classic rock all evening. I have a feeling that this played a part in the fact that we’ve been married for 6 years now. © Kinord / Pikabu

Story14
One time I got up the nerve to ask a really beautiful girl out, and she said yes. We decided to see a horror movie. I suggested it on purpose. I thought she’d get scared, I’d sit there fearless, comfort her, and she’d be impressed and want to date me.
But the movie was actually terrifying, and it wasn’t her clinging to me, it was me clinging to her! In the end, she said she didn’t want a coward for a boyfriend. © Overheard / Ideer

Story15
One time I was on a date and somehow managed to lose my credit card. It was cold, so while we were looking for it, I jokingly asked her what her worst date had been. She shot back, “What do you think it was?!” I never did find the card. © Overheard / Ideer

Story16
I asked a girl out for our first date — a romantic dinner by the river. We drove straight to the beach and had dinner. When it was time to go home, the car got stuck in the sand. I figured I must marry her — where else am I going to find a girl who all dressed up in heels would be helping me push a car out of the sand? © Overheard / Ideer

Story17
I have a friend who’s been on a short leash with his parents since childhood. That’s left him hyper-responsible, a little childish, and awkward with the opposite sex. But one time, things went so far that a girl actually agreed to go on a date with him. Naturally, I was dying to know how it went, and the next day I couldn’t resist calling him.
He said they met across town. They talked, laughed. The weather was nice and warm. The girl was cute and kind, and he wasn’t even nervous. About 20 minutes in, his phone rang. His dad was practically yelling down the line, “Get home, now!”
My friend jumped up, told the girl something had come up, and he had to leave immediately, said goodbye, grabbed a taxi, and rushed home. He skipped the elevator, ran up to the ninth floor, opened the door, and saw his dad standing there with a trash bag. He hands it to his son and says, “Why aren’t you taking out the trash?” © AlexandrRayn / Pikabu

Story18
I met a lovely, modest girl and asked her out on a date. Naturally, the conversation turned to work. She said she works as a consultant and quickly changed the topic. I assumed it was something like a sales consultant in some store and realized she was clearly embarrassed about her job.
I didn’t bring up that topic again. The girl captured my heart, so I started taking her out and buying little things for her. Spending money on her was enjoyable: she admired everything and just glowed. I felt proud that I was showering an unspoiled young lady with generous gifts.
I suggested we move in together and invited her to live in my 1-bedroom apartment with a mortgage. She agreed to move in but suggested living in her 2-bedroom instead. That’s when I found out that “consultant” meant she worked at a consulting firm and earned 3 times more than I do.
The girl laughed and said no one had ever cared for her so attentively before, and now she was sure that I wasn’t with her for the money. I still haven’t figured out how to react to that. © Overheard / Ideer

Story19
I got in touch online with a girl and set up a meeting at a shopping mall. I arrived at the agreed time, and so did she. We searched for each other for half an hour, but then realized that we were in different cities. © Darkhan / ADME

Story20
We set up a date for 2 p.m. and decided to just have some coffee. I arrived at 1:55, and the girl was already sitting at a table, holding a half-empty cup. I felt awkward and said I’d get myself a drink and, at the same time, order her another coffee and buy something from the pastries.
She refused, finished her coffee, and then just sat across from me without even trying to keep the conversation going. As soon as I took the last sip, she slapped her knee and stood up to leave. Alright, I got up too.
We left the coffee shop, and the girl said, “My car’s over there. It was nice meeting you!” Then she quickly turned and walked away without losing a second. We had parked almost next to each other, so I had to awkwardly follow her. And that’s how we walked, one after the other, in complete silence. © papayakob / Reddit

Leave a Reply Cancel reply