When you’re on a date, the aim is typically to create a great impression and keep things flowing smoothly. However, occasionally, the evening takes an awkward turn, transforming what could have been a perfect night into a total disaster. We’ve compiled 20 stories where people shared their most cringeworthy dating experiences.
He insisted on choosing the movie for our first date as a surprise. I told him, “No horror movies—I can’t handle them!” So you can imagine my frustration when the lights dimmed, and a horror film started playing. Five minutes in, I couldn’t take it anymore. I excused myself to the bathroom, fully intending to leave. But then I received a text from an unknown number saying, “Are you on a date with Ethan? I’m his girlfriend.” I stormed back into the theater and confronted him right there. He froze and muttered, “I was going to break up with her… eventually.” I walked out immediately.
On our first date, we went to a fancy restaurant. As soon as we sat down, she smiled at the waiter and asked, “What’s the most expensive dish on your menu?” My heart sank. I was prepared to pay for dinner, but I hadn’t budgeted for a meal that would leave me broke.
The waiter hesitated, glanced at me, and said, “I’m sorry, but that’s unavailable tonight.” She looked annoyed and tried asking about another pricey item, but again, it was “out of stock.” I ended up giving him a generous tip.
I went on a first date with a guy who claimed to be a foodie. He insisted on choosing the restaurant and ordering for both of us, saying, “Trust me, you’re going to love this place.” I was a bit skeptical but decided to go along with it. When the food arrived, I took one bite and felt my throat tighten.
Panicking, I told him I was allergic to shellfish. He just stared at me and said, “Oh, I didn’t think you were serious about that.” I had to leave immediately for treatment, and instead of being concerned, he stayed behind to finish his meal.
My wife went on a blind date a few years before we met. The guy had told her over the phone that he would be wearing blue jeans and a T-shirt. When she arrived at the venue and started waiting, he was nowhere to be found. After 40 minutes, just as she was about to leave, a guy in sweatpants and a T-shirt approached her with a smile and asked, “Are you waiting for me?” She replied, “Why aren’t you wearing what you described on the phone? I saw you, but I didn’t realize it was you.” He shrugged and said, “My mom hasn’t washed them yet.”
On my first date with my now-husband, we were both anxious and inexperienced with dating, which made us both incredibly nervous. Right before the date, I threw up. When he came to pick me up, we drove to the library, where we planned to use their Wi-Fi to watch Netflix in the back of the car.
As soon as we arrived at the library, he got out of the car and threw up in the parking lot. I then confessed that I had also thrown up right before the date. He tried to play it off as if we both had the flu or food poisoning, but we both knew it was just nerves.
My brother was downtown on a date with a girl when he discovered he was lactose intolerant. They shared ice cream, enjoying a lovely time, but while walking down the main street, the urge hit him. He panicked and ran off in the opposite direction, ducking behind some bushes to relieve himself.
Unfortunately, it was in front of an apartment building with balconies. Some guys partying on the balcony saw him and shouted, “Hey, look! That guy’s taking a poop!” Needless to say, he didn’t get a second date.
I thought it would be cute to try ice skating on a first date, despite not knowing how to skate. I was unaware that she was a competitive figure skater who skated circles around me. I realized it wasn’t going anywhere when she asked if she could do a few laps without me, as my beginner pace was too slow.
At 13, I went on my first date. She wanted to meet at a specific place and then go somewhere else, but I was terrible at knowing locations, so I asked my mom where it was. She gave me a ride and I thought she would leave, but instead, she got out to see what was happening.
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