People Share Their Dating Experiences That Went Horribly Wrong

In life, few things are as exhilarating as a promising date. The excitement, the conversation, and the hope for a connection beyond the ordinary are enough to keep us going. However, as many of us know, not every date is a dream come true.

Here are some unexpected tales of first dates gone wrong, proving that sometimes the best part of the night is when it’s finally over.

1. Thank God It’s Over

Let me tell you, I’ve never been so relieved for a date to end. It started innocently enough with a walk, but within minutes, he began unloading every complaint he could think of. “My boss is the worst,” he grumbled.

“My family doesn’t appreciate me, and nothing ever goes my way.” For over an hour, he didn’t stop—just one gripe after another, leaving me barely able to get a word in. I found myself counting the minutes, praying for an escape.

When we finally sat down at a restaurant, he arrogantly ordered for me without even asking what I wanted. “She’ll have the pasta,” he declared. Then, as if that wasn’t bad enough, he spilled juice all over himself because he ignored the bartender’s warning about the cap.

Instead of laughing it off, he launched into 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 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 any of them again.

2. Making the Exit

I was really looking forward to this date. We picked 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 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 commenting, “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 could feel myself getting more agitated with every second. I was already feeling 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 keep calm. “I figured since you’ve been on your phone all night and we barely talked, splitting the bill made sense,” I said, trying to keep my voice even.

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.

3. A Kiss for Two

I’ll never forget this date—it was like something out of 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 showed up, 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 of how to react. Was this a joke? My first instinct was to laugh, but the serious look on her face told me she wasn’t kidding. I could feel my expression freeze into a mix of confusion and awkwardness. A stuffed rabbit? To a comedy? I thought to myself.

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 have I gotten myself into? But she seemed genuinely fond of this giant, fluffy companion, so I nodded and went along with it, all while wondering how I was going to get through this 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 been on, but also one of the most memorable.

4. 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 thought, trying not to let my disappointment show. Still, I decided to stick it out. Maybe her personality will make up for it, I told myself, giving her the benefit of the doubt.

Just as I was starting 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 betraying the shock I felt. 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 non-stop 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. No way was I sitting through the rest of that. That was definitely the last blind date for me.

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 things 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 waltzed 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 went down. 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.

6. A Major Turn Off

Everything seemed fine on this dinner date—until the bill came. He reached into his pocket, and out slipped a wedding ring. My heart stopped for a moment as I stared at the ring, wondering if I was imagining things.

Is this guy actually married? I thought, a mix of shock and disgust bubbling up inside me. I watched him awkwardly fumble to pick it up, his face turning red.

He gave a nervous chuckle, clearly hoping to brush it off. “Oops, rookie mistake,” he said, flashing a sheepish grin as if it was no big deal. I couldn’t believe it. Was he really trying to laugh this off?

My mind raced, thinking about all the red flags I might’ve missed throughout the night. How could he sit there, pretending everything was fine, while hiding something like this?

But I wasn’t having it. I stared at him for a second, then without a word, I threw some cash on the table, stood up, and walked out. There’s no excuse for that kind of dishonesty.

7. Where’s the Check?

I was halfway through a pretty decent first date, enjoying the conversation and thinking things were going well. She seemed nice, and we were laughing about something when, out of nowhere, she casually dropped a bombshell. “Actually,” she began, taking a sip of her drink, “I’m engaged, but I’m not 100% sure he’s the right one.”

I froze, the fork halfway to my mouth. Did I just hear that right? I thought, staring at her in disbelief. She continued, completely unfazed. “So, I’m going out on a few dates to see if I change my mind.”

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.

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.