Valentine’s Day is marketed as a time of romance, candlelit dinners, and heartfelt gestures. But for some unlucky souls, it turns into a nightmare they’ll never forget. If you’ve ever felt bad about being single on February 14th, these disastrous date stories will make you feel like you dodged a bullet. Sometimes, solitude is the real happily ever after.

1. The Walking, Talking Human Notepad

Meeting someone from a dating app can be awkward, but this one took the cake.

“I met a guy from OKCupid. He seemed nice but never stopped talking. After the third or fourth interruption, I finally asked, ‘Do you want to hear anything I have to say?’

He apologized and said, ‘You’re right, I’m so sorry!’ Then he pulled out a pad of paper and a pen.

As I started talking, I noticed he was taking notes on everything I said. Confused, I asked what he was doing. He replied, ‘Oh, I’m just writing down things I want to tell you when it’s my turn to talk again.’”

Yeah… there was no second date.

2. Pokémon Cards: The Ultimate Romance Killer

A woman showed up for a first date at a bar, excited to meet a man she had been talking to online. But soon, things took a turn for the worse.

“He arrived with a large bag and sat down. Their conversation was already painfully forced when he suddenly reached into the bag and pulled out… a giant binder filled with his Pokémon card collection.

He lovingly flipped through each page, explaining every single card as if he was teaching a college lecture on rare Pokémon.

The woman, desperate for an escape, pretended she had an emergency and called a friend to come pick her up. He stayed and ate a plain hamburger alone.”

3. The Proposal That Went Wrong Before It Even Began

Public proposals can be romantic… or a complete disaster.

“A couple was sitting in a Mexican restaurant when the guy suddenly got down on one knee and proposed with a closed ring box.

His girlfriend, understandably, said, ‘Can I see the ring first?’

He opened the box, and after an awkward pause, she hesitated before finally saying, ‘Okay…’

The entire restaurant watched in horror. A couple sitting at a nearby table whispered, ‘That’s not a good sign.’ We all started wondering if they’d actually go through with it or if the marriage was doomed before it even began.”

4. Marriage Proposal on a Coffee Cup—With a Side of Betrayal

One guy thought he had a clever way to pop the question… but he didn’t consider his past mistakes.

“A man came into our coffee shop on Valentine’s Day and asked us to write ‘Will you marry me?’ on his girlfriend’s cup.

When we handed it to her, he got down on one knee.

She stared at the cup. Said nothing. Put it back down. And walked away shaking her head.

He was furious and started ranting about how she ‘should have gotten over him sleeping with her sister already.’

We had to ask him to leave.”

No amount of caffeine could fix that disaster.

5. A Restaurant Breakup Heard by Everyone

Some breakups happen in private. Others become public entertainment.

“A couple sitting in the center of the restaurant started arguing loudly. My manager politely asked them to take it outside.

Instead of calming down, the guy stood up, slammed his hand on the table, and yelled across the restaurant, ‘I’ve been wanting to do that for TWO YEARS now!’

Then he stormed out, leaving his date red-faced and humiliated in front of the entire crowd.”

Nothing says Happy Valentine’s Day like a two-year breakup grudge unleashed in a public setting.

6. A Tinder Scandal Unfolds at the Bar

Cheating is bad enough. Getting caught on Valentine’s Day? Even worse.

“A couple was enjoying their night out at the bar when a woman walked up to the girlfriend and said, ‘I think you should know—I matched with your boyfriend on Tinder, and we hooked up last week.’

The girlfriend refused to believe her. So the woman pulled out her phone and showed her the Tinder profile and their conversation.

By the time the boyfriend came back from the bathroom, he was greeted by a sobbing, screaming girlfriend and a woman exposing his lies.

The entire bar stopped to watch. It was like a live reality TV show. Messy, painful, and impossible to look away from.”

7. The Diamond Ring That Was Met With Complete Indifference

Not every woman swoons over expensive jewelry.

“A man at my restaurant handed me a sapphire and diamond ring and asked me to have the pastry chef place it on his partner’s dessert plate.

The chef went all out—decorating the plate beautifully with edible flowers, placing the ring delicately in the center.

When the woman received it, she picked up the ring, stared at it for a moment… then placed it on the table and continued eating her dessert without saying a word.

No excitement. No thank you. Nothing.

Safe to say, that was not the reaction he was hoping for.”

8. The Proposal That Started Strong… And Ended in Tears

At first, it seemed like a perfect moment. But something was very wrong.

“My wife and I were at Cheesecake Factory for lunch when we saw a man propose to his girlfriend.

The waitress was filming, people were clapping, she saw the ring and started crying happy tears. He smiled, and everything looked perfect.

But then, 20 minutes later, she was still crying—except now, it wasn’t happy tears.

They sat there talking in hushed voices, her face buried in her hands, while his smile disappeared. We don’t know what was said, but it definitely didn’t look good.”

9. The Date That Was Just Two People Talking to Themselves

Ever seen two people on a date, but it feels like neither of them is actually there?

“I was at a restaurant watching a painfully awkward first date. The weird part? Neither of them was listening to the other.

They both kept talking at the same time, completely ignoring what the other was saying.

It was two monologues happening simultaneously, and neither of them seemed to notice.

I was so fascinated by their complete self-absorption that I forgot to eat my own food. They were perfect for each other—just not in the way they thought.”

10. The Clown School Date That Ended in Disaster

“I was on a date with a girl who seemed amazing. We were chatting about careers, and I asked, ‘So do you really want to work in an office?’

She smiled, reached into her bag, and said, ‘Actually… I’m going to clown school.’

Then she pulled out a red clown nose and put it on.

I tried to laugh it off. ‘Oh, that’s cool. I didn’t know clown school was actually a thing.’

She got offended. ‘Oh no, it’s very competitive!’

I tried to recover, but it was too late. She took my joke as an insult to her entire career choice.

For a clown, she had a terrible sense of humor.”

Final Thoughts: Love Can Wait—Sanity Comes First

These stories prove that sometimes, being single is the real win on Valentine’s Day. If your only date this year is a box of chocolates and a cozy movie night, consider yourself lucky—you dodged some serious disasters.