10 Of The Most Awkward Valentine’s Day Stories Shared By Redditors That’ll Make You Rethink Your Plans

Manya Ailawadi

We’ve all been on embarrassing dates. But, Valentine’s Day brings in added pressure. While sitting at home alone is a safe choice, we sometimes want to join in as the town turns pink and red. It doesn’t always end up romantic, though. And, here are some embarrassing and not-so-romantic Valentine’s Day stories that redditors shared. 

1. “When I was 17, I went out for Valentine’s with my boyfriend. We were discussing gifts or whatever, and I said, “thank god you didn’t get me flowers. I hate them so much, and I think they’re stupid.”

He takes me to his trunk and pulls out flowers. Dumped me 2 weeks later. I totally deserved it.”

– GoochBucket

2. “Took my high school girlfriend out to a Mexican place for dinner a few years back. We both spent the evening with diarrhoea from food poisoning. It was so romantic.”

– AcutelyObtuse

3. “I was once dumped on Valentine’s Day, in a text message, sent from a borrowed cell phone, by a guy who had made a huge deal, multiple times about how his mom had always raised him to be a gentleman.”

– wisebloodfoolheart

4. “These two were on a date and the guy went to go use the bathroom, the girl just up and leaves after he went to the restroom. When the guy came back he sat around for awhile until asking his waitress where she went. She replied saying that she left. The guy then asked the waitress if she would go on a date with him. The waitress said no.”

– OffensiveGender

5. “A girl that I worked with went to lunch on Valentine’s Day at an expensive restaurant her boyfriend had gotten a reservation for, she got dressed up nice and was going on about how sure she was that he was going to propose.

He broke up with her.”

– Makabajones

6. “While working at a sushi bar in college I witnessed a blind Valentine’s day date where the guy who showed up was already the girl’s ex-boyfriend.”

– m0c0

7. “A guy I was dating gave me a few boxes of chocolate, which would’ve been sweet if I wasn’t allergic to dairy, which he knew.”

– mel0278

8. “A guy did a backflip and asked a girl to be his valentine… she declined. I walked up to him and asked if he was fine, he said it took him a week to perfect.”

– beejeko

9. “My then partner (a chef) decided to cook me a romantic dinner.

Long story short… the night ended with me in hospital because he/we set my hand on fire.

First and only time in ten years that we ‘celebrated’ V Day.”

– Opposedmoth

10. “A nice lady brought her kid in for dinner. Got seated at a table next to her husband and his mistress.”

– me-gusta-la-tortuga

Rethinking those Valentine’s Day plans?

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