15+ Hilarious First Date Fails That Will Make You Feel Better About Your Love Life

Bad dates can teach us important lessons for the future, even though they might be frustrating and disappointing. In the stories below, people share their memorable first dates with the world.

These experiences show how things can go wrong, but they also give us funny and sometimes awkward stories to remember. Each story highlights different situations where dates took unexpected turns, leaving lasting impressions on those involved.

Despite the mishaps, these stories remind us that dating isn’t always smooth sailing. From accidentally texting embarrassing messages to bringing moms along on dates, each tale adds a unique twist to the dating experience.

While some encounters end in laughter, others end in embarrassment or even surprise, like finding out you’ve unknowingly dated someone’s sibling. These stories show that even though bad dates can be challenging, they often become funny anecdotes to share later on.

1. I remember that date vividly. We had been together for almost a year when she received a phone call that shattered her. Her fiancé had tragically passed away in a motorcycle accident.
2. I made a terrible mistake on a date once. I accidentally sent a text saying “on the worst date of my life” to the girl I was out with.
3. My first date with him was at the zoo, and things took an unexpected turn at the entrance. He asked if I could pay for my own ticket, and then he used a 2-for-1 voucher, leaving me to foot the bill while he got in for free.
4. It started normally, but as we waited for the movie to begin, he pulled out his phone and showed me pictures of his ex-girlfriends. Talk about awkward!
5. While waiting in line at the bank, I witnessed a cringe-worthy attempt at flirting. The guy in front of me asked the teller out, only to be shut down because of his empty bank account.
6. He surprised me by bringing his mom along on our date. It wasn’t what I expected, but I decided to roll with it and make the most of the situation.
7. A friend set me up on a blind date at the movies. It turned out to be a disaster when the girl didn’t look like her online photos, and her family joined us, including her 9-year-old brother who kicked my seat the entire time.
8. Just when things were going well with her, she abruptly ended our date and started another one right in front of me. It was a humiliating experience.
9. I felt uneasy when my date kept taking pictures of me without my consent. The shutter sound gave them away, and it left me feeling uncomfortable.
10. It was going smoothly until I realized I had slept with her sister in the past. I ended the date early, hoping to avoid an awkward confrontation.
11. His wedding ring fell out of his pocket during dinner, making for an awkward moment that neither of us could ignore.
12. He was incredibly late for our date, and when he finally arrived, his excuse was unbelievable—he blamed his tardiness on his mom having to use the bathroom.
13. She surprised me by bringing mustard packets to a nice restaurant and insisted on enjoying them throughout the meal. It was bizarre and unforgettable.
14. The date was a disaster from start to finish—he played terrible music, swiped on Tinder during the movie, and bragged about his popularity with other girls.
15. During our date, she misplaced her phone, and when we tried to locate it, I discovered that I was saved in her contacts as “Free Food.” It was embarrassing.
16. Our first date took an unexpected turn when he accidentally hit my neighbor’s car while backing out of my driveway. Little did I know, it was just the beginning of our journey together—we ended up getting married.