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

Jacob Shelton
419 votes 206 voters 12.1k views 18 items

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.
1 34 VOTES

There's Nothing Like Dividing Assets Over a Bottle of Wine

There's Nothing Like Divid... is listed (or ranked) 1 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
Photo: via Imgur
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.
29 5
Agree or disagree?
2 33 VOTES

Not Even a Single Rose

Not Even a Single Rose is listed (or ranked) 2 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
Photo: via Reddit

The (presumably ex) boyfriend of HarukoBass was very anti-V-Day when he asked her what she wanted a few days before the holiday. Having a history of being stood up by exes she made a simple request: one red rose. He laughed in her face. The story gets rough from there.

"On the day, we went shopping, and he dragged me through the city bitching about how pathetic all these happy couples were. I got progressively more unhappy, partially at the let down of not having a special day with him, partially because his ego and feeling of superiority over everyone was getting tiring. He realized I was unhappy at about 11pm after laughing to himself all day, and said '"well there's nothing I can do about it now, you should have said if you wanted something."'

28 5
Agree or disagree?
3 46 VOTES

She Broke Up with Him Because He Rented a Car

She Broke Up with Him Because ... is listed (or ranked) 3 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
Photo: via Wikimedia
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!"
35 11
Agree or disagree?
4 52 VOTES

Maybe Sleep Through Valentine's Day Next Year

Maybe Sleep Through Valentine&... is listed (or ranked) 4 on the list People Reveal the Most Depressing Valentine's Days They've Ever Had
Photo: via Pinterest
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.
37 15
Agree or disagree?