People Share Their Dating Experiences That Went Horribly Wrong
Some dates are so painfully awkward that you wish they’d end before they even begin. These cringe-worthy moments will make you grateful for your own dating experiences, no matter how bad they may have been.
The anticipation of a promising date can be exhilarating—the conversation, the potential connection, the thrill of getting to know someone new. But as many of us have learned, 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 began as a simple walk quickly devolved into an hour-long venting session. He spent the entire time complaining about his boss, his unappreciative family, and how nothing in life ever seemed to go his way. I barely got a word in and found myself counting down the minutes until it was over.
When we finally sat down at a restaurant, he didn’t even ask what I wanted. “She’ll have the pasta,” he ordered, as if making a power move. Then, to top it off, he ignored the bartender’s warning about a drink cap and spilled juice all over himself. Rather than laugh it off, he launched into another rant. “Things are so much better in my country,” he grumbled, continuing to complain about everything around him.
When the check arrived, I suggested splitting it. He exploded. “Are you serious? You know my finances are a mess!” That was the last straw. I left cash on the table and walked out, but he insisted on walking me home. At my door, he had the nerve to say, “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 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 kept saying, barely looking up from her screen. Meanwhile, she ordered the most expensive dishes without even glancing at the menu.
I dropped subtle hints, clearing my throat and shifting in my seat, but nothing worked. Finally, when the waitress discreetly asked if we wanted separate checks, I didn’t hesitate. “Yes, please,” I replied, relieved. That’s when she finally looked up. “Separate checks?” she asked, clearly offended. “I thought you were paying!”
“Well, I figured since you’ve been on your phone all night, we’d split the bill,” I said. She scoffed, crossed her arms, and said, “A real man would’ve paid.” I calmly replied, “A real date would’ve involved conversation.” I paid my share, thanked the waitress, and left her there with her phone. Honestly, the exit was the best part of the night.
3. A Kiss for Two
This date felt like something straight out of a quirky rom-com. I was 18, in the Air Force, and my roommate had set me up with his girlfriend’s cousin. When I arrived 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. But she seemed serious, so I decided to roll with it. After the movie, when I walked her to her door, 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 met her, my first thought was, This is not the person from her photos. Still, I decided to give it a chance, hoping her personality would make up for the deception. 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 leaned over and whispered, “I’m going to the restroom.” Instead, I walked straight to my car and drove home. There was no way I was sticking around for that.
5. A Baffling Request
I once went on a date to the zoo. 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. But then, he pulled out a two-for-one voucher… and used it for himself, leaving me to pay full price!
I was stunned but tried to laugh it off. “You didn’t think to use the voucher for both of us?” I asked, hoping he’d realize how absurd 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
The dinner date was going fine—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 tossed some cash on the table and walked out. There’s no excuse for that level of dishonesty.
7. Where’s the Check?
I was on a pretty 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 how casually she said it. I didn’t want any part of her relationship drama. “Can we get the check, please?” I asked the waiter. I paid for my half, left, and never looked back.
These stories prove that, while some dates start with high hopes, they can go off the rails faster than you’d expect. At least we can laugh about them afterward!