From Dream Dates to Total Disasters: Read These Hilarious Dating Fails

Some dates are so awkward that you wish they could end before they even begin. The stories below show some cringe-worthy dating moments that will make you thankful for your own experiences.

In life, few things feel as exciting as a hopeful date. The thrill, the talk, and the hope for a special connection can keep us going. But, as many of us know, not every date is a dream come true.

Here are some surprising stories of first dates that went wrong, showing that sometimes the best part of the night is when it’s finally over.
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1) Thank God It’s Over

I was so relieved when my date finally ended. It started off okay with a walk, but just minutes in, he started sharing every complaint he had. “My boss is terrible,” he complained.

“My family doesn’t appreciate me, and nothing ever goes my way.” For over an hour, he went on and on, leaving me hardly able to speak. I found myself counting the minutes, wishing for a way out.

When we finally sat down at a restaurant, he ordered for me without even asking what I wanted. “She’ll have the pasta,” he declared. Then, he spilled juice all over himself because he ignored the bartender’s warning about the cap.

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

By the time the check came, I was done. I suggested splitting it, and he exploded. “Are you serious? You know my finances are a mess!” he yelled. I couldn’t take another second. I left cash on the table and walked out.

But it wasn’t over. He insisted on walking me home, and when we got to 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 made him back off.

The next day, his aunt called, trying to make things right. I told her, “Your nephew was completely out of line.” Thankfully, I never heard from any of them again.
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2) Making the Exit

I was excited about this date. We picked a nice restaurant, and I thought everything would go well—until she spent the entire meal on her phone. “Sorry, I just have to take this,” she said more than once, answering call after call.

Meanwhile, she ordered the most expensive items on the menu—a $25 appetizer, a $45 steak, and a $15 drink—barely even looking up from her screen.

I tried giving her hints that I was bothered by her behavior, 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.

Every time I tried to engage, she was back on her phone, and I felt myself getting more annoyed with every second. I was already uncomfortable when the waitress came by and discreetly asked, “Would you like separate checks?” Without hesitation, I nodded and said, “That would be great.”

That’s when she finally looked up from her phone. Her eyes widened, and she gave me a surprised look. “Wait, separate checks?” she asked, her tone suddenly sharp. “I thought you were going to cover it.”

I raised an eyebrow, trying to stay calm. “I thought since you’ve been on your phone all night and we barely talked, splitting the bill made sense,” I replied.

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 think I’d be dining with your phone the entire night.”

She stared at me, stunned. “I can’t believe this. You know, a real man would’ve just paid without making a fuss.”

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 walked out, leaving her sitting there with the bill and her phone. Honestly, that exit was the best part of the night.
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3) 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 go to the movies, and when I arrived, she was carrying this huge blue stuffed rabbit. “This is Pebbles,” she said, holding it proudly. “I always bring him to the movies for comfort.”

I blinked, unsure how to react. Was this a joke? My first thought was to laugh, but the serious look on her face told me she wasn’t kidding. I felt my expression freeze in a mix of confusion and awkwardness. A stuffed rabbit? To a comedy? I wondered.

I forced a smile, not wanting to seem rude. “Oh… Pebbles, huh?” I managed to say, trying to sound casual. My mind raced, though. What had I gotten myself into? But she seemed to really like this giant, fluffy companion, so I nodded and went along with it, all while wondering how I was going to get through the evening without bursting out laughing.

I couldn’t believe it, but hey, I went along with it. After the movie, when we got to her front door, she smiled and said, “You have to kiss me… and Pebbles.” I froze for a second, but she was so cute that I went ahead and kissed both her and the rabbit. It was definitely one of the weirdest dates I’ve ever had, but also one of the most memorable.
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4) Calling It Quits

Blind dates are always a risk, 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 thought, trying not to let my disappointment show. Still, I decided to stick it out. Maybe her personality would make up for it, I told myself, giving her a chance.

Just as I started to relax, she dropped a bombshell. “Oh, by the way, my parents and little brother are joining us for the movie,” she said casually, as if this was completely normal. I could feel my eyes widen in disbelief.

Her family? I thought, trying to keep my face from showing my shock. I forced a smile, but inside, I was scrambling. This isn’t a date; this is a family outing! But I didn’t want to be rude, so I nodded and thought, Okay, I’ll see how this goes.

We sat through “Gnomeo and Juliet,” and it wasn’t long before her nine-year-old brother started kicking the back of my seat. Tap. Tap. Tap. I gritted my teeth and tried to focus on the movie, but after 20 minutes of nonstop kicking, I couldn’t take it anymore.

This is a disaster, I thought, every tap pushing me closer to the edge. I leaned over to her and whispered, “I’m just going to use the restroom.”

As soon as I stood up, I knew I wasn’t coming back. I walked straight to my car and drove home without a second thought. There was no way I was sitting through the rest of that. That was definitely my last blind date.
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5) A Baffling Request

I once went on a date to the zoo, and right at the entrance, he casually turned to me and asked, “Do you mind covering your own ticket?” I was caught off guard, but I thought, Okay, I’m an independent woman; that’s fine. So I smiled and said, “Sure, no problem,” trying to keep it light.

As we approached the ticket booth, I reached for my wallet, and that’s when he pulled out a two-for-one voucher. Oh, that’s nice, I thought, assuming he was about to save us both some money.

But then, to my shock, he handed the voucher to the attendant, used it for his ticket, and walked right in for free while I paid full price for mine. My jaw almost dropped. Did that just happen?

I stood there for a second, stunned and trying to process what just happened. I couldn’t believe it. Did he really just let me pay while he got in for free? I tried to brush it off, but inside, I was fuming. As I caught up to him, I asked, “So… you didn’t think to use the voucher for both of us?”

He shrugged, completely unbothered. “Oh, I figured since you said you didn’t mind, it wouldn’t be a big deal.”

I was speechless. Not a big deal? I didn’t even know how to respond, so I just nodded and kept walking. But in that moment, I knew one thing for sure—there wasn’t going to be a second date.