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4 Crazy, Hilarious Valentine’s Day Stories

It’s almost that time of year again. It's the “looks like it’s time to avoid drug stores, Tinder and all my friends in relationships” time of year — aka Valentine’s Day. For some reason, we —or should I say Hallmark and card companies — have decided that this holiday matters. And that decision has led to all sorts of disappointments, wild adventures and embarrassing tales for lovers everywhere. Here are four of the most outstanding V-Day debacles:


1. The Cooties Catcher

“In seventh grade, I had a huge crush on this guy in my class. The day before Valentine’s day, he made some flirty allusion that convinced me that he was bringing me something special — a card, candy or something. I was so excited. I already had my outfit for the next day picked out, and I was giddy with anticipation. That night, I was brushing my hair in the bathroom when a little white bug fell onto the countertop. I reached up and found droves of them crawling all over my scalp. I had head lice. Needless to say, I didn’t spend that Valentine’s Day swooning over my homeroom crush. Instead, I spent it leaning over a tub as a lice removal specialist combed over my head and drenched my hair in chemicals. I still can’t smell tea tree oil without being reminded of the worst Valentine’s Day I’ll probably ever have.”

- The Cooties Catcher


2. The Broken Besties

“My junior year of high school, my best friend and I suffered awful heartbreaks simultaneously. About two days before Valentine’s Day, she broke up with her boyfriend of two years; the very same day, one of my other close friends began dating the guy to whom I had recently admitted my romantic feelings. Needless to say, he rejected me and began dating her. So, my bestie and I were left to our pillowcases and pints of Ben & Jerry’s. That weekend, we decided we needed to get away. We ended up spending the actual holiday in my family’s isolated woodland cabin — no heart-shaped candy, no romantic movies, and definitely no boys.”

-The Broken Besties  


3. The Late Bloomer

“Freshman year, a boy in my class asked me out on a date to the movies on Valentine’s Day. However, I didn’t exactly realize it was a romantic thing so I showed up with one of my female friends, and we all watched “The Lego Movie” awkwardly. Then, a few days later, I told a friend about the experiencs. She paused and asked, “are you sure you’re not gay?” I didn’t know it then, but I definitely am.”

-The Late Bloomer


4. The Parent Trap

“It was the first Valentine’s Day with my very religious, yet closeted, gay boyfriend who has extremely protective parents. As you can tell, this night was going to end tragically. As luck would have it, Northeast Ohio got pummeled with a snow storm that night. His insanely protective parents would not let him leave the house to go on our romantic dinner date initially. They gave up eventually, though, when I offered to pick him up under the justification that I’m from Michigan, therefore better at driving in the snow. Continuing this tragic series of events, my parents decided to crash our romantic Thai dinner. My first real Valentine’s Day date I was squished in between my parents, with my boyfriend across the table. I believe we then ended the night on my couch watching a very un-sexy documentary while making out with his extremely chapped lips.”

-The Parent Trap


The moral of the story: despite what we are often encouraged to believe — thanks to social media and the touchy couple in the restaurant — not everyone has a Valentine’s Day straight out of a daydream. So, if you ever think that you’ve had a rough go of it at love, just remember, it probably could've been worse!

Kate Nerone is a lifelong writer of fiction, non-fiction, essays and poetry. She grew up in the San Francisco Bay Area where she received numerous awards for both fiction and non-fiction works. She is a featured author in Declare What You Know to Be True, an anthology by students of the Intuitive Writing Project. Her passions include acting, writing, dancing, podcasting, shopping at Trader Joe's, and requesting snapchats of her dogs from her mom. She attends the University of Wisconsin-Madison where she is involved in Her Campus, Love Wisconsin, Hillel, WSUM, the film department and more. She has interests in pursuing creative writing, acting, filmmaking, journalism, and communication arts.
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