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People Reveal Their Most Disastrous Dating Experiences

Bored couple sitting at a bar | Source: Getty Images
Some dates are so awkward that you wish they’d end before they even start. The stories below dive into cringe-worthy dating moments that will make you appreciate your own experiences.

In life, few things are as thrilling as the anticipation of a promising date. The excitement, the conversation, and the potential for a meaningful connection are what keep us hopeful. However, as many know, not every date turns out to be magical.

Bored couple sitting at a bar | Source: Getty Images

Here are some unexpected tales of first dates gone wrong, showing that sometimes the best part of the night is when it finally ends.

  1. Thank God It’s Over

    I’ve never been so relieved for a date to end. It began innocently enough with a walk, but within minutes, he started unloading every complaint imaginable. “My boss is the worst,” he said.
    “My family doesn’t appreciate me, and nothing ever goes my way.” For over an hour, he kept ranting—one gripe after another—leaving me with no chance to speak. I found myself counting the minutes, desperately wishing for an escape.

A man and a woman having a conversation | Source: Pexels
When we finally sat at a restaurant, he arrogantly ordered for me without asking what I wanted. “She’ll have the pasta,” he announced. Then, as if that wasn’t bad enough, he spilled juice on himself because he ignored the bartender’s warning about the cap.

Instead of laughing it off, he launched into a tirade. “Things are so much better in my country,” he snapped, criticizing the staff and everything around him.

A man and a woman at a restaurant | Source: Pexels

By the time the check came, I’d had enough. I suggested splitting it, and he exploded. “Are you serious? You know my finances are a mess!” he shouted. I couldn’t take it anymore. I left cash on the table and walked out.

A woman leaving a restaurant | Source: Pexels

But it wasn’t over. He insisted on walking me home, and when we reached my door, he said, “You owe me something for this date.” I pushed him away and said, “If you don’t leave, I’ll call the police.” That finally got him to back off.

The next day, his aunt called, trying to smooth things over. I told her, “Your nephew was completely out of line.” Thankfully, I never heard from them again.

Couple having an argument outdoors | Source: Shutterstock
  1. Making the Exit

    I was really looking forward to this date. We chose a nice restaurant, and I thought things would go well—until she spent the entire meal glued to her phone. “Sorry, I just have to take this,” she said repeatedly, answering call after call.
    Meanwhile, she ordered the priciest items on the menu—a $25 appetizer, a $45 steak, and a $15 drink—barely glancing up from her screen.

A man and a woman looking at the menu | Source: Pexels

I tried to signal my annoyance, clearing my throat, shifting in my seat, and even saying, “It’s hard to get to know someone when they’re so busy.” But she didn’t even notice.

Young woman checking her phone on a date | Source: Getty Images

Every time I tried to engage, she returned to her phone, and I grew more irritated with each passing second. I was already uncomfortable when the waitress discreetly asked, “Would you like separate checks?” Without hesitation, I nodded and said, “That would be great.”

A woman checking her phone in a restaurant | Source: Pexels
Finally, she looked up from her phone, surprised. “Wait, separate checks?” she asked sharply. “I thought you were going to cover it.”

I raised an eyebrow. “Considering you’ve been on your phone all night and we barely talked, splitting the bill seemed fair,” I said, keeping my tone calm.

A woman holding a cellphone | Source: Pexels
She scoffed, crossing her arms. “Are you serious? You’re really going to make me pay after inviting me out?”

“Well,” I replied, “I didn’t expect to dine with your phone the entire night.”
She stared, stunned. “I can’t believe this. A real man would’ve just paid.”
I shook my head. “A real date would’ve involved some actual conversation,” I shot back.
That’s when I knew it was over. I paid my part, thanked the waitress, and left her with the bill and her phone. Honestly, leaving was the highlight of the night.

A woman checking her phone at a restaurant | Source: Pexels
  1. A Kiss for Two

    I’ll never forget this date—it felt like a scene from a movie. I was 18, in the Air Force, and my roommate set me up with his girlfriend’s cousin. We decided to see a movie, and when I arrived, she was carrying a huge blue stuffed rabbit. “This is Pebbles,” she said proudly. “I always bring him to the movies for comfort.”

Woman holding a large teddy bear | Source: Getty Images
I blinked, unsure of how to react. Was this a joke? My first instinct was to laugh, but her serious expression said otherwise. A stuffed rabbit? To a comedy? I wondered.

I forced a smile. “Oh… Pebbles, huh?” I managed, trying to sound casual while thinking, What have I gotten myself into? Still, I nodded and went along with it, determined to make it through the evening without laughing.

A close-up of a man smiling at the camera | Source: Pexels

After the movie, at her front door, she smiled and said, “You have to kiss me… and Pebbles.” I froze for a moment but found her so endearing that I kissed both her and the rabbit. It was one of the weirdest, yet most memorable dates I’ve ever had.

A couple kissing | Source: Pexels
  1. Calling It Quits

    Blind dates are always a gamble, but this one… wow. I arrived at the theater, and as soon as I saw her, my stomach dropped. She looked nothing like her Myspace photos. Is this the same person? I wondered. Still, I decided to give her a chance.
    Just as I started to relax, she casually said, “Oh, by the way, my parents and little brother are joining us for the movie.”

A man holding a bucket of popcorn | Source: Pexels
Her family? I thought, trying to mask my shock. This isn’t a date; it’s a family outing! But not wanting to be rude, I went along with it.

We sat through “Gnomeo and Juliet,” but her nine-year-old brother kept kicking the back of my seat. Tap. Tap. Tap. By the 20th minute, I couldn’t take it anymore.

Couple eating popcorn while watching a movie in a cinema | Source: Pexels

“I’m just going to use the restroom,” I whispered to her, and as soon as I stood up, I knew I wasn’t coming back. I walked straight to my car and drove home. That was the last blind date for me.

A man standing beside cinema chairs | Source: Pexels
  1. A Baffling Request

    I once went on a date to the zoo, and at the entrance, he casually asked, “Do you mind covering your own ticket?” Caught off guard, I thought, Okay, I can handle that. So I smiled and said, “Sure, no problem.”
    At the ticket booth, I reached for my wallet, and he handed over a two-for-one voucher. Nice, I thought, assuming he’d save us both money.

Young couple on a date to a zoo | Source: Getty Images
Instead, he used the voucher for his ticket and walked in for free while I paid full price. I was stunned. Did that just happen?

Catching up to him, I asked, “You didn’t think to use the voucher for both of us?”

A woman gesturing | Source: Pexels
He shrugged. “You said you didn’t mind,” he replied, unfazed.

I nodded, furious but silent. At that moment, I knew there wouldn’t be a second date.

A woman walking | Source: Pexels
  1. A Major Turn Off

    Dinner was going fine—until the bill arrived, and a wedding ring slipped out of his pocket. My heart stopped. Is this guy married? I wondered, staring in disbelief.
    He awkwardly picked it up and laughed nervously. “Oops, rookie mistake,” he said.

Shocked woman rejecting a man’s proposal | Source: Shutterstock

I couldn’t believe it. Was he really trying to laugh this off? Without a word, I threw some cash on the table, stood up, and walked out. There’s no excuse for dishonesty.

A couple having coffee | Source: Pexels

7. Where’s the Check?
Halfway through what seemed like a decent first date, she casually mentioned, “Actually, I’m engaged, but I’m not 100% sure he’s the right one.”

I froze, fork mid-air. Did I just hear that right? She continued, completely unfazed, sharing all the doubts about her fiancé as though I was her therapist.

By the time the check arrived, I already knew I wasn’t going to see her again. But then, she gestured to the bill and said, “Oh, I forgot my wallet! Can you get this?”

I paid, but I left without saying another word. What was supposed to be a date felt more like an awkward counseling session I didn’t sign up for.

Dissatisfied shocked black man listening to an excited and emotional woman talking | Source: Shutterstock


It was like she was discussing the weather, not her engagement. My mind raced, trying to process the fact that I had been unknowingly dragged into her relationship drama. How is she this casual about it? I wondered, my appetite suddenly gone.

I stared at her, completely speechless, trying to figure out how to respond. Finally, I turned to the waiter and said, “Can we get the check, please?” He looked just as shocked as I was. I paid, left, and that was the end of that.

A man holding a chopstick | Source: Pexels

These stories show that while some dates start with high hopes, they can quickly take a turn for the worse, leaving you grateful when they’re finally over.