Dating can be an exciting adventure filled with laughs, unexpected moments, and the hope of meeting someone special. But anyone who’s been on more than a few dates knows that not every one of them turns into a love story. In fact, some dates are so awkward or strange that you just want to escape as fast as possible.
Let’s take a look at some funny and surprising dating moments that went hilariously wrong. 😅
1. “I’m Glad It’s Over”
A woman shared her nightmare date on Reddit. From the very beginning, her date complained nonstop about his life for an entire hour, barely letting her speak. Feeling frustrated, she excused herself to the bathroom just to cool off and nearly drove home instead.
Things only got worse at dinner. He bragged about how superior his home country was, ordered food for her without asking, spilled juice on himself, and loudly criticized the restaurant staff. Later, he went on a rant about wanting to be a boss so he could fire people he thought were useless. When the check arrived and she suggested splitting it, he yelled at her. She calmly left money on the table and walked away.
Not wanting to cause a scene, she reluctantly let him walk her home. The walk was painfully silent, and when they reached her door, he tried to force himself on her. She pushed him away, threw money at him, and told him to leave. Later, his family heard about what happened and stopped speaking to her.
2. Making the Exit
One Reddit user went on a date with someone who insisted on dining at a fancy restaurant. The problem? Their date spent the entire time glued to their phone, answering calls and texts. The waitress noticed and quietly brought two separate checks. The user paid their share immediately and took the opportunity to leave without saying much.
3. A Kiss for Two
An 18-year-old man in the Air Force went on a blind date set up by a friend. They watched a movie together, and his date brought along a giant stuffed rabbit named Pebbles. Afterward, they got ice cream and drove to her cousin’s house. Before going inside, she asked him to kiss both her and Pebbles so the stuffed animal wouldn’t feel jealous. Confused but trying to be polite, he actually did it.
4. Giving Up
A man went on a blind date only to discover his date looked nothing like her online photos. Things got worse when she brought him to the movie theater with her parents and nine-year-old brother. The brother kicked the back of his seat the entire movie. Halfway through, he went to the bathroom and just drove home instead.
5. A Strange Request
A woman was stunned when her date asked her to pay for her own ticket at the London Zoo on their first date. He proudly showed her a two-for-one coupon that got him in for free while she still had to pay full price. Awkward but she agreed.
6. A Big Turnoff
During dinner, a woman watched her date pull out his wallet and a wedding ring fell out of his pocket. Without saying a word, she threw cash on the table and walked out. Her appetite disappeared instantly.
7. Where’s the Check?
A man was shocked when his date casually mentioned she was already engaged but wanted to go on a few more dates with him just to be sure her fiancé was “the one.” He immediately asked for the check and left.
Dating can be a roller coaster sometimes fun, sometimes painfully awkward. Stories like these remind us to laugh at the disasters and appreciate the good moments even more. Not every date will go perfectly, but every now and then, you might just meet someone truly magical. ✨
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