true stories People Reveal the Most Depressing Valentine's Days They've Ever Had  

Jacob Shelton
199 votes 122 voters 7.7k views 18 items Embed
It seems that for most people, Valentine's Day is hit or miss. Unfortunately, the people who have the worst Valentine's Day stories seem doomed to repeat their mistakes. Whether they suffered the indignities of a date who was too drunk to finish dinner, or they threw up after eating at the saddest salad bar on earth, the lonely hearts on this collection of depressing Valentine's Day stories that were posted on Reddit have had a rough time with Cupid’s favorite holiday. If you’re giving up on love this Valentine’s Day, open up a heart-shaped box of chocolates, pour another glass of wine, and keep reading to find out about these Reddit users who revealed their most depressing Valentine stories.

If this Valentine's is making you feel like an unloved ogre, then cheer yourself up with these stories of terrible relationships, and some of the worst Valentine's gifts that have ever been given. Hopefully, the Redditors who shared their tales for this list of the most depressing Valentine's Day stories ever won’t be repeating the bummers of their past. After reading these sad stories it’s important to know that even if one Valentine's was bad, that doesn’t mean that every year has to follow the same pattern. So if you’re having an off day this Valentine's, just read these stories and realize that your day could be much worse.

Vote up the most depressing Valentine’s Day stories, and if you’ve had a rough holiday tell everyone about it in the comments.
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She Broke Up with Him Because He Rented a Car


She Broke Up with Him Because ... is listed (or ranked) 1 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
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A Redditor had this to say about his depressing date: "I went out of my way and had my dad rent me a car for the weekend, and planned an incredible night, dinner, ice skating, and a few other things. So one night she asked how I was going to go about doing Valentine's Day with her when I didn't have a car, and I told her I was planning on renting one so it wouldn't be a problem. Tried calling her, no answer, no returned calls. I tried e-mailing her, no response. Then the next day I called and she finally answered. When I asked what happened, she replied, "Sorry, I feel kinda bad but, I decided to do something else. I found it kind of pathetic that you rented a car, it's sort of sad - not really the kind of guy I wanna date. But we can still be friends!"
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There's Nothing Like Dividing Assets Over a Bottle of Wine


There's Nothing Like Divid... is listed (or ranked) 2 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
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A few years ago, on Valentine's Day, Reddit user KrispieKrape spent the evening dividing her assets with her husband in preparation for separation. Hopefully she bought herself some flowers.
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Maybe Sleep Through Valentine's Day Next Year


Maybe Sleep Through Valentine&... is listed (or ranked) 3 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
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On Valentine's Day 2015 a Reddit user treated herself to a new vibrator and got a bad UTI from using it. That's not exactly a great way to end an evening.
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His Girlfriend Broke Up with Him Before the Bouquet Arrived


His Girlfriend Broke Up with H... is listed (or ranked) 4 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
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This Redditor's girlfriend broke up with him on Valentine's Day, via text, and immediately received the $100 bouquet he bought for her.