People Share Their Dating Experiences That Went Horribly Wrong
Some dates are so awkward that you wish they’d end before they even begin. These cringe-worthy moments will make you thankful for your own dating experiences, no matter how bad they may have been.
In life, few things are as exciting as the anticipation of a promising date—the conversation, the potential connection, the thrill of getting to know someone new. But, as many of us know all too well, not every date turns out to be a dream come true.
1. Thank God It’s Over
I’ve never been so relieved for a date to end. What started as an innocent walk quickly turned into an endless stream of complaints. He spent the entire time unloading about how much he hated his boss, how his family didn’t appreciate him, and how nothing ever seemed to go his way. He didn’t stop for over an hour, and I barely got a word in edgewise. I was counting the minutes, desperate for an escape.
When we finally sat down at a restaurant, he didn’t even bother asking what I wanted. He just ordered for me. “She’ll have the pasta,” he said, like it was a power move. As if that wasn’t bad enough, he ignored the bartender’s warning about a drink cap and spilled juice all over himself. Instead of laughing it off, he went on another rant. “Things are so much better in my country,” he grumbled, complaining about everything around him.
When the check came, I suggested splitting it, but he exploded. “Are you serious? You know my finances are a mess!” he yelled. That was it. I left cash on the table and walked out, but it didn’t end there. He insisted on walking me home, and when we reached my door, he said, “You owe me something for this date.” I shoved him away and told him if he didn’t leave, I’d call the police. The next day, his aunt called me to try to smooth things over, but I was done. I never heard from him—or his family—again.
2. Making the Exit
I was really excited about this date. We picked a nice restaurant, and I thought things were going well—until she spent the entire time glued to her phone. “Sorry, I just have to take this,” she said, over and over again, barely looking up from her screen. Meanwhile, she ordered the most expensive things on the menu without even paying attention.
I tried giving her hints, clearing my throat and shifting in my seat, but nothing worked. Finally, when the waitress came by and discreetly asked if we wanted separate checks, I didn’t hesitate. “Yes, please,” I said, relieved. That’s when she finally looked up from her phone. “Separate checks?” she asked, clearly offended. “I thought you were paying!”
“I figured since you’ve been on your phone all night, we’d split the bill,” I replied. She scoffed, crossed her arms, and said, “A real man would’ve just paid.” I calmly responded, “A real date would’ve involved conversation.” I paid my part, thanked the waitress, and left her there with the bill and her phone. Honestly, that exit was the best part of the night.
3. A Kiss for Two
This date felt like something out of a quirky rom-com. I was 18, in the Air Force, and my roommate set me up with his girlfriend’s cousin. When I showed up to pick her up for the movies, she was holding a giant blue stuffed rabbit. “This is Pebbles,” she said, “I bring him to the movies for comfort.”
I blinked, unsure of how to react. I wasn’t sure if I should laugh or roll with it. But she seemed serious, so I decided to go along with it. We watched the movie, and when I walked her to her door afterward, she smiled and said, “You have to kiss me… and Pebbles.” I hesitated but went ahead and kissed both her and the rabbit. Definitely one of the strangest dates I’ve ever had, but also one of the most memorable.
4. Calling It Quits
Blind dates are always a gamble, but this one… wow. When I saw her, I immediately thought, This is not the person from her photos. But I decided to give it a chance. Maybe her personality would make up for it, I thought. Then she casually mentioned, “Oh, by the way, my parents and little brother are joining us for the movie.”
Her family? On a first date? I didn’t want to be rude, so I smiled and went along with it. But her nine-year-old brother spent the entire movie kicking the back of my seat. After about 20 minutes of that, I whispered, “I’m going to the restroom.” Instead, I walked straight to my car and drove home. No way was I sticking around for that.
5. A Baffling Request
I once went on a date to the zoo, and right at the entrance, my date turned to me and said, “Do you mind covering your ticket?” I didn’t think much of it at first. No big deal, I thought. Then he pulled out a two-for-one voucher… and used it for himself, leaving me to pay full price for my ticket!
I was stunned but tried to play it off. “You didn’t think to use the voucher for both of us?” I asked, hoping he’d realize how ridiculous it was. He shrugged and said, “I figured since you didn’t mind, it wasn’t a big deal.” That’s when I knew there wouldn’t be a second date.
6. A Major Turn Off
Everything seemed fine on this dinner date—until the bill arrived, and out slipped a wedding ring from his pocket. My heart sank as I stared at it. “Oops, rookie mistake,” he said with a nervous chuckle, trying to brush it off. I was floored. Was he married? I couldn’t believe the audacity.
Without saying a word, I threw cash on the table and walked out. There’s no excuse for that kind of dishonesty.
7. Where’s the Check?
I was enjoying a decent first date when, out of nowhere, she dropped a bombshell. “I’m engaged, but I’m not sure he’s the one, so I’m going on a few dates to see if I change my mind.” I froze, shocked by her nonchalance. I didn’t know what to say, but I quickly realized I wasn’t interested in being part of her relationship drama. “Can we get the check, please?” I said to the waiter. I paid, left, and never looked back.
These stories prove that while some dates start with high hopes, they can quickly go off the rails. But at least we can laugh about them afterward!