People Share Their Dating Experiences That Went Horribly Wrong

Some dates go so disastrously wrong that you wish they could end before they even begin. The following stories capture some of the most cringe-worthy and unexpected dating mishaps that people have shared.

In life, there are few experiences as thrilling as a promising date—the anticipation, laughter, and the hope of a meaningful connection. Yet, anyone who’s been on a fair share of dates knows that not every outing leads to a storybook romance.

1. Thank God It’s Over

One woman shared her dating disaster on Reddit, recounting how her date began to unravel before it had even really started. The man spent the first hour of their walk complaining about every aspect of his life, never once letting her get a word in.

Things took a sharp turn when they sat down at a restaurant. He ordered for her without asking, dismissed the bartender’s warning about a tricky bottle cap, and promptly spilled juice on himself. His arrogance only grew, berating the staff and boasting about the supposed superiority of his home country.

As the date dragged on, he revealed his ambitions to become a manager just so he could fire people. When the bill arrived, she suggested they split it due to his earlier rants about money, which led him to yell at her. She left her share on the table and walked out, but he insisted on walking her home. The walk was tense, and at her doorstep, he tried to force himself on her, claiming she “owed” him. She pushed him away, threw more money at him, and slammed the door, threatening to call the police if he didn’t leave.

The next day, she faced the audacity of his aunt, who defended him, but the woman made it clear his family had failed to raise him right. She never heard from them again, and she didn’t mind one bit.

2. Making the Exit

Another Reddit user recalled his first date with a girl who insisted on an expensive restaurant. She ordered a $25 appetizer, a $45 steak, and a $15 drink but spent the entire time glued to her phone, taking calls and responding to texts.

Noticing this, the waitress discreetly approached the man and offered to prepare separate bills. He gladly accepted, paid for his own meal, and went home, leaving his date to deal with her hefty tab.

3. A Kiss for Two

At 18, a man in the Air Force was set up by his roommate with his girlfriend’s cousin. They went to the movies as a group, but his date showed up carrying an oversized stuffed blue rabbit named Pebbles. She explained it gave her comfort during movies—even though they were watching a comedy.

After the movie, the group went for ice cream and then headed to the cousin’s house. When they arrived, his date suggested he kiss both her and Pebbles goodnight to avoid making the rabbit jealous. Though baffled, the man obliged, reflecting later that despite her quirkiness, she was still an attractive date.

4. Calling It Quits

A man’s friend once set him up on a blind date. They met at the theater, where he quickly realized her appearance differed greatly from her Myspace photos. To make things worse, she brought her parents and nine-year-old brother along for their movie date to see “Gnomeo and Juliet.”

Trying to make the best of it, he endured the movie, all while her brother kicked the back of his seat nonstop. After 20 minutes, he’d had enough. He excused himself to the restroom and never came back, driving home instead.

5. A Baffling Request

On Twitter, a woman shared her experience of a date to the London Zoo. At the entrance, her date casually asked if she could cover her own ticket, to which she agreed. Then, to her shock, he pulled out a two-for-one voucher, meaning she paid for her ticket while he entered for free.

6. A Major Turn-Off

While on a dinner date, a woman was stunned when her date’s wedding ring fell out of his pocket while he was reaching for his wallet—a clear sign he was married. Horrified, she threw some cash on the table and left. She was so disgusted that she lost her appetite entirely.

7. Where’s the Check?

On a first date, a woman told the man, “I’m actually engaged, but I’m not sure he’s the right one. So, I’m going on a few dates to see if I change my mind.” The man wasted no time and immediately asked for the check before making a hasty exit.

Have you ever been on a date that took a terrible turn?