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My Worst Valentine's Day Ever: Stories from DealsPlus Visitors

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February 12, 2016 · 9.2k Views


Valentine's Day is one of those holidays where you either love it or hate it, there’s no middle ground. If you’re in a committed relationship it can be a lovely excuse to go above and beyond in the romance department. On the other hand, if you’re unhappily single, it can sometimes be a cruel reminder of that reality.

We took to Twitter to ask our readers to tell us the story about their worst Valentine’s Day ever, and you guys didn’t disappoint. Here are some of our favorite submissions, hopefully your Valentine’s Day goes a lot better than these!


What's Your Worst Valentine's Day Ever?



  • “I asked a girl out on a date. We went to this really nice restaurant downtown, and I started getting stomach pains before we started eating. Halfway through the meal, I had to excuse myself and ran off into the restroom, having to deal with some extreme diarrhea. I took about 45 minutes in the restroom, and by the time I got back, my date was gone. The food was good though, 10/10 would eat there again. Preferably with some imodium.”


  • “Back in high school I had a long distance relationship with my first love. When he said he wasn't coming to visit, it was my opportunity to find a new Valentine just for the upcoming school dance that was going to be taking place. I didn't want to go alone when all my friends had dates. On the night of the dance, my boyfriend surprised me by coming to the dance after all! After seeing that I was with another guy, he threw punch at my date and they got into an all out brawl. By the end of the night, I ended up with no boyfriend, no date, and alone.”


  • “One year in college, my then-boyfriend and I were in a long-distance relationship so we decided to make Valentine’s Day special since he was coming to visit me. I’m not exactly a baking maven, but I thought it’d be nice to surprise him with heart-shaped snickerdoodle cookies since those were his favorite. Using amateur-level, boxed cookie mix, I whipped up the batter and stuck them in the oven. At the ding of the timer, I opened the oven door to retrieve the cookies, but between all the hot oven heat invading my face and the fear that I would somehow drop all my hard work into the oven or onto the floor, I burned my arm on the oven rack. I ended up sulking over the painful, red mark on my arm for a good part of the night.”

  • "My worst Valentine's Day ever happens every year. All my friends have significant others so instead of tagging along and being a third wheel like usual, for Valentine's Day i just stay home wearing a Snuggie, eating Ben and Jerry's ice cream out of the carton, while watching Grey's Anatomy. "


  • “One year I made my boyfriend a heart shaped pillow...only to come over 2 days later and see his dog laying on it in the hallway by the bathroom.”


  • “One year in early February, my girlfriend at the time was asking me what I wanted to do for Valentine's Day. I told her let’s not make a big deal about it, and just go out on a date like normal. I was trying to trick her into thinking I wasn’t going to get her anything, even though I was already beginning to plan out a romantic evening. Well my trick must have worked a little too well, because she dumped me a week before Valentine's Day. To make matters worse, it was the very same day I had been out shopping for her gifts.”

  • “My date and I had been together for a while, but we had taken a break and were in the process of getting back together. We still loved each other. We spent a lovely Valentines evening together that included dinner, a movie, and great conversation. Then while I was cuddled up next to him all happy as could be, he told me that he had been seeing another girl while we were apart and had been "trying to find the right time" to tell me. Needless to say, we never got back together.”


  • “My best friend decided to come stay for the weekend and my romantic dinner of steaks on the grill quickly was engulfed in blue flames.  We had to make do with the sides as dinner since it was late in the evening by then.”

  • “My boyfriend wanted to be extra prepared for Valentine’s day so he bought some flowers a few days ahead of time so he would have them ready to give to me on the day of. He had no idea that the lifespan of cut flowers were very short. To make it worse, he believed they needed sunlight to stay healthy so he put them in sunlight for a few days. By the time I received them, they were dry and half dead.”


  • “One year, my boyfriend at the time went to his ex-girlfriend's birthday party instead of seeing me...which was taking place in the apartment right next door to me.”


  • "I went on a vacation with my boyfriend at the time, and the vacation ended on Valentine's Day. On our 12 hour car ride home my boyfriend broke up with me, about one hour in. Most awkward car ride ever..."


  • “My worst Valentine's Day happened when I let my friend talk me into going to a speed dating event in Las Vegas that was trying to break a world record. There were four times more women than men, so they were literally pulling guys off the street and signing them up. Nothing like 10 forced minutes with 25 strangers. I was done after about 15 switches, but they wouldn't let us go.”


  • "I was dating this guy. The week before Valentine's Day I was talking to him on the phone and he said he didn't believe in participating in the holiday since it was "corporate made." So I didn't expect him to ask to be my Valentine. The day after Valentine's Day I saw he was tagged on Facebook pictures with another girl. Flowers, chocolates and even a stuffed animal."


  • “My date took me to Taco Bell and gave me a box of chocolates that were 2 years old. I tried to eat a truffle, but it was rancid.  When we got home I became very sick. Don't get me wrong, I love Taco Bell, but it wasn't the ideal Valentine's Day date!”


For more about Valentine's Day, check out these other related posts:

sfgiantsfan8 profile picture
A lifelong Bay Area native, Matt Spillar graduated in 2013 from Fresno State with a Sports Marketing degree. He strives to combine his passion for sports marketing along with his interests in finance and budgeting. In his spare time, he writes for his personal blog, spillsspot.com
blackfootFeb 12, 2016
Lol, These are funny. Nice read:)

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