Valentine’s Day Date Horror Stories: 3 Women Share Their Most Insane, Jaw-Dropping Dates

Last Updated on March 11, 2025

Valentine’s Day is supposed to be the most romantic day of the year—filled with love, flowers, and the perfect opportunity for a Valentine’s Day date, whether it’s a candlelit fancy dinner or a unique night of entertainment. But for some women, their Valentine’s Day date is a perfect night they’d rather forget. These three women share their real-life Valentine’s Day date horror stories, proving that sometimes, love is truly a battlefield.

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Valentine’s Day Date Horror Stories

1. The Threesome Proposal… With His Mom?! (And a Shocking Plot Twist)

“I had been dating this guy, Ryan, for about two months, and Valentine’s Day was our first ‘big’ romantic night. He made a huge deal about taking me somewhere special, so I was excited. He picked a fancy rooftop restaurant with stunning views, and the vibes were perfect—until the check came.

I offered to split, but he insisted on paying. I thought, ‘Wow, a gentleman!’ But the next morning, I woke up to a Venmo request for half the bill—down to the cent, including tax and tip. The note? ‘Romance ain’t cheap.’

I was shocked. But here’s where it gets worse. He then texted, saying, ‘I have a special request for you and my mom. We should all get to know each other… intimately.’

Yes. His mother.

Instead of blocking him immediately, I decided to play along. I acted intrigued and told him I’d be open to the idea. His excitement was off the charts. He gave me an address for the ‘special night’ and told me his mom was ‘eager to meet me.’

But when I arrived, I wasn’t alone. I walked in with Ryan’s dad.

The look on Ryan’s face? Priceless. His mom, sitting beside him in a silk robe, looked equally horrified. Turns out, his dad had no idea about the weird stuff Ryan and his mom were up to.

Ryan stammered, trying to explain, but I simply turned to his dad and said, ‘You might want to sit down for this.’ His dad stormed out, his mom ran after him crying, and Ryan sat there sweating bullets.

I left that night thinking it was over, but a month later, I found out through friends-of-friends on Facebook that Ryan’s parents had filed for divorce. Apparently, after that night, Ryan’s dad started putting pieces together, and some deep, dark family secrets unraveled.

Best accidental homewrecker moment ever.”

–Erica, 27

2. The Accidental Mistress Turned Vengeful Ex… And the Apartment Heist Gone Wild

“I had been casually seeing this guy, Nate, for about six months. He wasn’t big on labels, but we spent a lot of time together. So, when he asked me out for a Valentine’s romantic dinner, I assumed we were taking the next step.

Everything was going great—until the waitress approached our table, looking visibly uncomfortable. She kept looking at me, then at Nate, before whispering, ‘Hey, uh… didn’t you come here last night?’

Nate turned pale. He tried to brush it off, but I could tell something was up. The waitress didn’t back down. She finally said, ‘You were here with someone else—she even had a heart-shaped necklace you gave her.’

I immediately grabbed my purse and left. But instead of crying, I did some FBI-level digging. Turns out, Nate had three girlfriends—one of whom was pregnant.

So what did I do? I messaged all three of them, and we allied. One of the girls still had access to his apartment and let us in. We didn’t just trash his place—we took everything.

TV? Gone. Sneakers? Gone. The fridge? Emptied. We even took his gaming console, his entire bed frame, and his pet fish. Yes, we took the fish.

Then, we left a framed picture of the four of us holding hands with the words ‘CHEATER’ in lipstick.

He texted me that night saying, ‘You didn’t have to go that far.’ Oh, but we did. And his fish is now thriving in my aquarium.”

– Jasmine, 32

3. The Cops Showed Up… and So Did His Wife… and His OTHER Wife (And the Mistress With a Knife)

“This was a first date from a dating app, and I should have known it was doomed when he texted me ‘wyd’ instead of making actual plans. But I gave him a chance because he seemed cute and charming.

We met at a casual bar, and within 10 minutes, he was already talking about his ex. Not in a ‘I’ve moved on’ way, but in a ‘She was the love of my life, and I’ll never find someone like her’ way. I smiled politely, sipped my drink, and kept looking for an escape.

Then, things got really bad. He pulled out his phone and started scrolling through old texts from his ex, reading them out loud. He even showed me a picture of them together on a past Valentine’s Day!

I was about to fake an emergency, but before I could, a woman stormed into the bar. She was screaming his name, throwing drinks, and calling him a liar. Turns out? That was his WIFE.

But here’s where it gets insane.

Another woman walked in. She took one look at the first wife and went, ‘Oh, you must be the other wife.’

Yes. He had two wives. And neither of them knew about each other.

As they started yelling at him, yet another woman entered. She was holding a knife.

She was his mistress, and she had just found out about both wives. The bar was pure chaos.

The bartender called the cops, and just as they arrived, the guy tried to run. He tripped over a barstool, faceplanted, and got tackled by security.

I finished my drink, tipped my bartender, and walked out as if nothing had happened.

Best date night ever.”

– Mia, 24

Final Words…

These nightmare dates prove that while love is in the air on Valentine’s Day, so is absolute insanity, deception, and alliance. Have you ever had a Valentine’s Day horror story? Share it in the comments—we could all use a good laugh (or have the perfect opportunity to stay home next year).