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The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

By Ariel Wodarcyk - February 13, 2020
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Every February, it feels like the pressure is on to have a picture-perfect Valentine’s Day. But whether you’re single, partnered or navigating ambiguous friends-with-benefits territory, the supposedly loveliest day on the calendar often turns out being anything but.

Whether the day is ruined by a shockingly oblivious boo or the death of a fellow movie-goer (yes, that happened), there are a lot of ways that February 14th can go wrong. Below, we gathered 20 people’s most laugh-out-loud, outrageous Valentine’s Day experiences.

 

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Meredith had found the perfect romantic restaurant for her Valentine’s date with her college boyfriend (now husband). “But when we got to the address, it didn’t exist.” The couple settled in at a T.G.I. Friday’s instead, where they were seated at a shaky table. The “nasty” waitress messed up Meredith’s order. Paul and Meredith still tipped her—but only $2. So, “she chased us out of the restaurant and threw my money back at me,” Meredith said.

Unfortunately, this was the better half of the night. When their top-choice movie was sold out at not one but two theaters, they again went with the flow and saw The Royal Tenenbaums instead. Three-quarters into the movie, Meredith heard a scream: There was a medical emergency. EMTs arrived shortly after and, with the movie still rolling, wheeled out a dead woman on a stretcher.

Only after the EMTs left did the screen go blank. “We were all just sitting in this movie theater with no movie playing thinking about how a fellow audience member just died,” Meredith said. “Then they turned the movie back on—20 minutes rewound.” The night ended with the couple missing their train home and getting into a huge argument. But don’t worry—they’re now married with two wonderful children.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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There are a lot of stories about unreciprocated feelings on Valentine’s Day, but few involve appealing to a judge on an undeserving bae’s behalf. Reddit user Daisesandink once dated a man with three traffic citations that had gone unpaid for so long, they were moved to warrant status.

Because Daisiesandink worked in the legal field at the time, she went to court and pled the warrants back down to citations. She even paid the $15 fee per ticket. “I saved this guy well over $2,000 and got several points off his driving record in a matter of minutes,” she said.

Her caring spirit didn’t stop there. The next week was Valentine’s Day, which she spent making a home-cooked meal and getting dolled up in a new dress and lingerie. “I’d just gotten the food on the stove and the candles lit when he called and said he wouldn’t be over.” Daisiesandink was understandably confused.

“That’s when he proceeded to break up with me and tell me that he only used me for my legal contacts to get his warrant taken care of. It completely broke my heart.” Luckily, Daisiesandink had the last laugh. “I found out he got another ticket the day after Valentine’s.”

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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When Redditor Hangoneveryword’s boyfriend dumped her over the phone while she was visiting her dad on Valentine’s Day, she figured there was no way the day could get any worse. But an hour later, her mom called sobbing because she had a “knock-down, drag-out fight” with her boyfriend.

Meanwhile, OP’s stepmom was called into work by her verbally abusive boss on this Saturday. “My poor, shellshocked father, dealing with three crying women, tried to make it better by taking my stepmom and I to a movie at the end of the day,” Hangoneveryword said.

By the time her stepmom got off work, though, the family missed the movie they wanted to see and settled for something none of them cared about. Just before dining out that night, Hangoneverword’s dad dropped her and her stepmom off outside the restaurant. When he pulled around to park, he was hit by an oncoming car. He was fine—but the car was totaled. “Worst Valentine’s Day ever,” Hangoneveryword said.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Valentine’s Day can be a make-it-or-break-it holiday if you haven’t defined the relationship. But Taylor wasn’t trying to do anything other than hook up on V-Day with the guy she had been casually seeing for two months. He turned her down. “He didn’t want me to think it was relationship sex,” she told Better You.

“I was devastated because Valentine’s Day is a sex holiday to me.” She stuck around for a chill night playing video games, “which is more relationship-y in my opinion.” Apparently, this guy was cool with having sex on any other day, so he and Taylor continued seeing each other until she moved away that spring.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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This one hurts. When Reddit user Dogboat  was in high school, she was thrilled to celebrate Valentine’s Day with her first boyfriend. “We made plans to hang out at his place after school. So I got the recipe for his favorite cookies from his mom and made them, baked him brownies, and got his favorite candy bars and put them in a big heart-shaped box.

On the outside of the box I wrote a bunch of reasons why I liked him.” When Valentine’s Day came and Dogboat presented her boyfriend with her thoughtful gifts, he showed up empty-handed. “He told me he didn’t get me anything because he thought I was joking about being excited for Valentine’s Day.” She was still looking forward to spending time with him after school, but her boyfriend had forgotten their plans and ditched class early to play video games at home.

“I stood outside his last class like a dumbass waiting for him to come out and he never did,” she said. She used his teacher’s phone to call her boyfriend’s parents, who were kind enough to pick her up from school. “But instead of taking me to their house, they took me home because my boyfriend wound up leaving right after I called to go to a friend’s house,” Dogboat said.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Here’s another high school romance gone awry on V-Day. In her senior year of high school, Nicole couldn’t wait for her first real Valentine’s Day date. Imagine her surprise when his parents, his sister and his sister’s fiancé joined them for dinner. “His parents drove us there and got out of the car,” Nicole told Better You.

“And my blood was just cold.” Nicole’s boyfriend’s parents already disapproved of their relationship, but she didn’t think they would go so far as to involve themselves in their Valentine’s plans. The parents paid, but the meal wasn’t very filling. “I drove myself home and got McDonald’s on the way back to comfort myself,” Nicole said.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Hannah’s professional cyclist boyfriend told her they were going to take a “short, romantic bike ride” to have a picnic together. “But then he made me bike, like, 10 miles,” Hannah told Better You. “He put me in a bike uniform and gave me his mom’s fancy bike with the clip-in shoes that I did not know how to work.

The sun was blaring, I was sweating like a sinner in church and I had to keep stopping for water because I couldn’t ride the bike and grab the bottle from the rack underneath at the same time.” She was so frustrated she started to cry—but her boyfriend was too far ahead of her to notice.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Hannah’s second February 14th fiasco took place with another boyfriend at a San Francisco spa. She described the facility as “super clean, with a little couch-bed, sauna and hot tub.” She and her man relaxed in the hot tub for 45 minutes. But right after they left, they both noticed a rash spreading across his neck. “It looked like he’d been stung by 7,000 bees,” Hannah said.

His skin was intensely itchy. “We went to the urgent care ER because he was freaked out that it was flesh-eating bacteria,” Hannah said. “They gave him some cortisone and said, ‘Go home.’” Hannah’s skin was totally fine. The couple actually returned to the facility several times afterward, but stuck to the saunas.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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A week before Valentine’s Day, Reddit user Voco landed in the hospital with diabetic ketoacidosis, which had her throwing up all weekend. She had to convince her boyfriend to drive two hours to Seattle to come visit her. He did reluctantly, because “he was afraid of driving in the city and it was a pain in the ass for him.”

When Voco was released from the hospital the day before V-Day, he still expected her to visit him! “I could barely walk without passing out,” Voco said. The couple got into a huge fight and skipped Valentine’s Day together.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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High school senior Emmy bought her boyfriend of eight months chocolates and “a stuffed animal that looked like him—a puppy with blue eyes.” Meanwhile, the holiday slipped his mind. Thankfully, “his mom got me two pairs of fuzzy socks with Superman hearts on them,” Emmy said.

How did she know the gifts were from her boyfriend’s mother? He told her: “My mom got these for you because I didn’t get you anything.” Some people just can’t tell even white lies.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Having a birthday that falls on Valentine’s Day is tough because most of your friends are too busy with their sweethearts to celebrate with you. The year Reddit user and Valentine’s Day baby Deathofregret turned 21 was especially rough—she suffered vertigo due to a double ear infection, caused by a sinus infection.

And she couldn’t even get a little liquid courage. “Because I was on antibiotics, I couldn’t drink,” she said. “And because it was Valentine’s Day, everybody had dates.” We hope she’s had many better birthdays since.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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The sting of unrequited love runs deep, especially in Reddit user Peachbot’s  case. Her boyfriend told her he loved her two days before Valentine’s Day. She said it back, expecting the holiday and following months (maybe years) to be full of romance.

But her partner’s heart was more fickle. Two days later, he got back together with his high school sweetheart. Seems like a quick turnaround to fall in and out of love with someone.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Sometimes it’s better to receive nothing at all, than a gift with no meaning behind it. When Reddit user Amyria  was in her first relationship to coincide with Valentine’s Day, her boyfriend got her “a single wilty flower, only because his friend made him get it after I’d been subtly hinting to the friend all day.”

He also presented her with a classy card, featuring “cartoon-y tools” on the front and “something along the lines of having a choice between getting hammered or screwed.” How sweet? “All of it was clearly picked up without thought on the way to my house, where we just sat watching TV for two hours,” Amyria said. “Then he claimed to be tired and went home…but actually went to the casino instead because he was a gambling addict.”

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Reddit user Sduncan1980 had both a relationship and a friendship dissolve on Valentine’s Day. He booked a surprise trip to Barcelona, complete with “a great hotel, a great restaurant” and plans to propose to his sweetheart of three years.

“We were due to leave early the next morning, so I was also preparing a nice meal for that evening and [wanted to] surprise her with the tickets just after,” he said. When he arrived at the home they shared, her car was already in the driveway, although he didn’t expect her home for another hour.

“I unlocked the front door and gave a quick shout—nothing,” he said. After cooking and even showering, he walked into their bedroom—and found her having sex with his supposed friend. Instead of flipping out, “I pulled my suitcase from the top of my wardrobe and packed as many clothes as I could get into it. And then left.” He went to Barcelona on his own.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Some people go to great lengths to get through to their partner, especially Redditor Wisebloodfoolheart’s ex-boyfriend. “I was dumped 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.”

While it was hurtful, she now realizes she’s better off. “In retrospect, that guy was dumb as a box of rocks.” Of course, he tried crawling back to her. “I got mine in the end because six months later, he tried to apologize and get back together. Uh, nope.”

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Oh, to be a kid falling in love again (literally). In fourth grade, Reddit user Godblessmrswalker brought a chocolate rose to his crush’s doorstep. When his mom pulled up to the girl’s house, “I opened the car door, rose in hand, beaming,” Godblessmrswalker said.

“And then I snagged my foot on the strap of my backpack, which was in the floorboard. Fell on the pavement right in front of the girl and a few of her neighborhood friends.” He still handed his crush the candy rose, but was too embarrassed to say anything.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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One Valentine’s Day, Reddit user Bowyer-betty’s girlfriend gave him “a stuffed dog and a sweet heartfelt declaration of love…that was written for the guy that she just broke up with to be with me.”

But don’t worry, she scratched out her ex’s name and wrote Bowyer-betty’s on the envelope instead. “She just figured, ‘F*ck it, it’s already written and sealed,’” he said. “We didn’t last long.”

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Reddit user Smallbatchb  started off with good intentions by staying in and watching horror movies with a fellow single friend. Then a mutual friend who worked at a strip club invited them to come for Valentine’s Day $1 Singles Night. By 2 a.m., their funds running low and only one beer in, Smallbatchb and his pal called it a night.

As they drove home, his friend missed a sign warning them to turn at the next light. Then they were speeding down a one-way light rail track, going the wrong way. “Obviously we got pulled over within minutes and were assumed to be drunk because, well, that would actually make more sense,” Smallbatchb said.

“After proving we were sober, we were given a ticket and headed back home to finish our terrible horror movie.”

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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There’s nothing wrong with a low-key Valentine’s Day, provided all parties are on board. That wasn’t the case for Reddit user Thefabulousbomb.  When she gave her boyfriend a small present and “a really lovely card with a nice, heartfelt message,” he told her he still had to write hers.

But when she asked for the card after she cooked him a steak dinner, he still hadn’t written it. The couple had a huge fight, which ended with Thefabulousbomb sleeping on the couch for the night. “The next day, he gave me my card that literally said, ‘To Fabulous, from ——.’” That made Thatfabulousbomb realize her boo was less than fabulous. “We broke up a few months later,” she said.

The 20 Worst Valentine’s Day Experiences Real Romantics Have Ever Had

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Finally, we get to hear from someone who was the catalyst for another person’s disappointing holiday! When Reddit user Landlubber77 came to school with a rose in hand, his girlfriend, Jessica, ran up to him assuming that the flower was for her. Not so fast, Jessica! Landlubber77 told her the rose was for another girl, and that he had to “just try with her or he’ll always wonder ‘what if.’”

To soften the blow, he suggested one final makeout session with Jessica, during which he stuck his gum on her knee to save it for after their kiss. Yes, her knee. It seems Landlubber77 did what was best for him, because he and the girl he actually gave the rose to ended up marrying and having a son together. As of his post, they had been together for 14 years. “Sorry, Jessica!” he said.