Going on a date can be an exciting experience—meeting someone new, sharing laughs, and maybe even finding a real connection. But let’s be honest: not every date turns into a fairy tale romance. Sometimes, they go so wrong that all you want to do is disappear.

We’ve all heard (or maybe even experienced) those painfully awkward, cringe-worthy dates that make us rethink the whole dating game. From bizarre requests to jaw-dropping behaviors, these dating disasters prove that sometimes, you just have to laugh it off.

Here are some of the funniest, weirdest, and most uncomfortable dating horror stories that will make you appreciate even the most boring dates.

1. Thank Goodness That’s Over

A woman on Reddit shared one of her most dreadful dating experiences. It all started when her date spent the entire first hour complaining about his life. While she tried to be polite, she barely got a word in as he went on and on about his struggles. Feeling frustrated, she excused herself, pretending she needed to use the restroom, and seriously considered just driving home right then and there.

Unfortunately, things only got worse. At the restaurant, he took it upon himself to order for her without asking what she wanted. While eating, he managed to spill juice all over himself—yet instead of laughing it off, he turned it into a rant about how much better his home country was and rudely criticized the restaurant staff. As the night dragged on, he kept rambling about his dream of becoming a manager just so he could fire people he deemed incompetent.

When the check arrived, she attempted to split it, but he exploded in anger. She quickly placed money on the table and got up to leave. He insisted on walking her home, and in an effort to avoid making a scene, she reluctantly agreed. The walk was painfully silent, and when they reached her door, he suddenly tried to push himself against her. She shoved him away and even gave him some money, demanding that he leave.

The story didn’t end there. His family later heard about the disaster of a date, and instead of supporting him, they sided with her—cutting ties with him altogether.

2. The Art of a Quick Exit

Another Reddit user shared a date story that makes a strong case for putting your phone away during dinner. Their date had insisted on going to a fancy restaurant, but once they arrived, the person barely looked up from their phone. They spent the entire evening texting, answering calls, and completely ignoring their dinner companion.

Sensing the discomfort, the waitress discreetly split the bill into two separate checks. Seizing the opportunity, the Reddit user paid their half, excused themselves, and walked out, leaving the date to enjoy their phone in peace.

3. A Kiss for Two… Including a Stuffed Rabbit

At 18, an Air Force recruit agreed to go on a date set up by a friend. It started off simple—a movie followed by ice cream. However, things took a bizarre turn when his date arrived carrying an oversized stuffed rabbit named Pebbles.

After the movie, they headed to her cousin’s house. As they reached the door, she turned to him and made an unusual request: he needed to kiss her and Pebbles. Apparently, she didn’t want the stuffed rabbit to feel left out. Awkward but wanting to be polite, he went along with it, giving both of them a peck before making his escape.

4. The Blind Date Nightmare

A man agreed to go on a blind date set up by a friend, but the surprises didn’t stop at just meeting someone new. When he arrived at the theater, he immediately noticed that his date looked nothing like the photos she had posted online. He decided to stay and give it a shot—only to realize things were about to get even weirder.

Instead of a one-on-one date, she brought her parents and her nine-year-old brother. The family dynamic wasn’t the issue—it was the fact that her little brother spent the entire movie kicking the back of his seat. After enduring as much as he could, the man finally had enough. Instead of sticking around for the rest of the evening, he told his date he needed to use the restroom… and went straight home instead.

5. The Cheapest First Date Ever

A woman was left speechless when her date took her to the London Zoo but expected her to pay her own way in. He proudly pulled out a two-for-one coupon, which meant he got in for free while she had to pay full price for her ticket.

It was an odd move, to say the least. While she went along with it, it’s safe to say there was no second date.

6. A Wedding Ring in the Pocket? No Thanks.

A woman was enjoying what seemed like a normal dinner date until she noticed something shocking. As her date reached for his wallet, a wedding band slipped out of his pocket.

She froze, realizing she had unknowingly been on a date with a married man. Disgusted, she immediately threw some cash on the table, got up, and left—losing her appetite in the process.

7. The Ultimate Red Flag

Some dating red flags are subtle, but others are impossible to ignore. One man was out with a woman when she casually dropped a bombshell: she was engaged.

She explained that while she loved her fiancé, she wanted to go on a few more dates just to be sure she was making the right decision. The man wasted no time—he asked for the check, paid, and walked out without another word.

Final Thoughts

Dating is a wild ride—you never know what you’re going to get. While some dates lead to love, others become cautionary tales of what not to do. If you’ve ever had an awkward or embarrassing date, take comfort in knowing you’re not alone.

At the end of the day, bad dates make for great stories. And who knows? The next one might just be the one.

Have you ever had a date go horribly wrong? Share your funniest (or most cringe-worthy) experience in the comments! And don’t forget to share this with friends who could use a good laugh.