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15 Most Hilarious Valentine's Day Stories From Our Staff And Community

15 Most Hilarious Valentine's Day Stories From Our Staff And Community

Ah, Valentine's Day! The one day of the year dedicated to love. Someone is thinking “everyday is a day of love”. Well, you are right but even though 🤣. It's a day that so many look forward to! I mean, who doesn't love an excuse to shower their special someone with chocolates, flowers, and romantic gestures? Love ittt!

Peace was no exception. She had planned an elaborate date night with her boyfriend, complete with a fancy restaurant, movie tickets, and a surprise weekend away. But the night before Valentine's Day, she got a nasty case of food poisoning. Instead of a romantic evening, she was in the hospital, receiving treatments and feeling sorry for herself. And to add icing to an already painful cake, her boyfriend served her premium breakfast! But as it turns out, Peace wasn't the only one who had a bad experience on Valentine's Day.

Ladies and Gentlemen, gather around and get ready to laugh your hearts out because we have the juiciest stories for you. We have gathered 15 funniest Valentine's Day stories from the Heroshe staff and our community. Whether you are single, taken, or enjoy drinking tears from heartbroken people, these stories will have you laughing and shaking your head in disbelief. Here's to a Valentine's Day gone wrong!

Kanessa Muluneh:
Last year my husband bought me 10 roses, 1 for each year we've been together. When I told him that we've been only together for 8 years, he later confessed that he just got a discount from the florist because he bought 10 and he couldn't refuse as it was a good deal.

James Green, Owner, Cardboard Cutouts:
A few years ago I decided that I wanted to surprise my wife with a romantic Valentine's Day dinner. I decided to cook her some lasagna, which is her favorite. Now, I'd never cooked lasagna before, but I figured— how hard could it be? I found a recipe online and followed it step by step.

On Valentine's Day, my wife came home from work and was delighted to find the house filled with the aroma of lasagna. I proudly presented his creation to her, but as we sat down to eat, we quickly realized that something was wrong. The lasagna was extremely salty and had an unusual texture.

As we struggled to eat the salty lasagna, my wife noticed something strange in her piece. It turned out that I had accidentally used a whole container of salt instead of the recommended tablespoon.

Despite the ruined dinner, we had a great time laughing and joking about the experience. We ordered takeout and spent the rest of the evening cuddled up on the couch, enjoying each other's company. From that day on, my wife always teases me about my cooking skills, but we both know that we will always remember the Valentine's Day when w head the saltiest lasagna in history.

Robert Davidson, CEO at Nc Cutting Tools:
My high-school English teacher was well known for being a fair, but hard, grader. One day I received a B minus on a theme paper. In hopes of bettering my grade and in the spirit of Valentine's season, I sent her an extravagant heart-shaped box of chocolates with the pre-printed inscription: “BE MINE.” The following day, I received in return a Valentine from the teacher. It read: Thank you, but it’s still BE MINE-US.’”

Rinal Patel, the founder of Webuyphillyhome:
Once, my friend decided to surprise his girlfriend on Valentine's Day by dressing up as a giant cupid. He spent hours creating the perfect costume and even practiced his arrow-shooting skills.

On the big day, he snuck into his girlfriend's office and jumped out from behind a desk, shouting "Happy Valentine's Day!" Unfortunately, he had forgotten to consider how his costume might affect his balance, and he stumbled and fell right into a potted plant. Dirt and leaves went flying everywhere, and he ended up tangled up in the plant.

His girlfriend was initially stunned, but then she couldn't stop laughing at the sight of him covered in dirt and leaves. In the end, they spent the rest of the day cleaning up the mess and laughing about the hilarious surprise gone wrong.

Angela, Content Moderator at Vyvmanga:
I had been seeing a guy named Mike for a few months and was excited to spend their first Valentine's Day together. Mike had promised to take her out for a romantic dinner, and I had spent all day getting ready for the big night.

As we sat down to order at the restaurant, the waiter came over to take their drink order. Mike ordered a beer, but when it was my turn, I nervously blurted out, "I'll have a strawberry milkshake, please."

Mike looked at me with surprise, and I felt my face turning bright red. I tried to laugh it off, but Mike couldn't stop teasing me about my choice of drink. Our dinner was a bit awkward, with Mike constantly making jokes about my milkshake, but I tried my best to play along. When the bill came, Mike offered to pay, but I insisted on splitting it, feeling a bit embarrassed by my milkshake mishap. As they walked outside, I noticed a street vendor selling heart-shaped balloons. I thought it would be a fun way to salvage the evening, so I bought one and gave it to Mike as a joke.

But just as we were about to leave, a gust of wind caught the balloon and pulled it out of Mike's hand. We watched in horror as it floated up into the sky and disappeared from sight. Mike turned to me with a serious expression and said, "Well, I guess we'll just have to come back next year and try again. "I burst out laughing, and we spent the rest of the evening walking around the city, enjoying each other's company and making jokes about their Valentine's Day mishaps. Even though it wasn't the perfect evening we had planned, we both had a great time and made some funny memories to laugh about in the future.

Dotun Olajiga:
Mine was the memory of a Valentine's Day gift in my pre-degree year. Val fell on a Sunday. After church service was over, dude walked up to me with a sincere smile and gentle energy, said happy Val, gave me the bag and left. I got back to my hostel and looked in the bag. I saw one sardine, two sachet tomatoes, and onions!

You can try imagining the look on my face that day but you won't get it right. My roommates laughed at me but still ate the concoction I made with the gifts.  

Rita, Heroshe:
He promised me the best Valentine's day gift then on the day of, the gift was a phone call wishing me Happy Valentine's Day.

Fola, Heroshe:
In 2016, I made up my mind to confess my love to my crush on Valentine's Day. She and I had been talking for a while and I had engineered some talking points to infuse in my confession message. I copied the message from my drafts that morning and sent the message to her just before I left home for work.

One hour later, I got to work and saw that the BBM message had been read but the recipient was none other than my line manager who was namesakes with my crush! I quickly retracted the message but needless to say my former colleagues still tease me about it.

Dolapo, Chain Reactions Africa:
My ex-boyfriend took my ATM card to buy me a gift. Make it make sense.

My boyfriend (and now husband) sent me a dozen roses to commemorate how many months we had been together. Unfortunately he had the wrong address and my neighbors claimed they didn't receive any packages with my name on it.

On Valentine's Day, my date never showed up. I later found out he had ghosted me, but not before I had already ordered two entrees and three desserts.

Bisola, Union Bank:
I received a gift box at work from my female bestie. My colleagues were excited so I decided to unbox it in their presence. The unboxing started great. There were two vials of scented oils, a jar of my favorite scented candles, a box of Hershey's chocolate, amongst other things. All amazing gifts. Until we got to the bottom of the box where an adult toy sat. There was an awkward silence as my colleagues dispersed and I wanted the earth to swallow me.

Ju-ju, TSR:
I thought I was going to spend Valentine's Day alone, but then both my ex-boyfriend and my current boyfriend showed up at my door with flowers. Probably the worst experience ever.

My ex-boyfriend broke up with me via SMS on Valentine's Day so I decided to drown my sorrow in a bucket of ice-cream I had in the fridge. Turns out it was expired and I spent most of the day vomiting and in the hospital.

Abiola, Opera News:
I decided to go all out for my ex-girlfriend on Valentine's day. I got her customized bracelets, a pair of earrings, and a lovely black gown. I didn't even get boxers and singlets for my efforts. All I got was a WhatsApp message saying: thanks.

Valentine's Day can be a day filled with romance, love, and appreciation but it can also be a day with hilarious moments and unexpected surprises. We hope that these stories brought a smile to your face and reminded you that even if your Day doesn't go as planned, it can still be a memorable experience. It does not matter if you spend the day with family, your significant other, or alone, remember to cherish the moments and laugh at the unexpected. Who knows, maybe next year you will have your own hilarious Valentine's Day story to share.

Afolabi Ojabowale

Afolabi Ojabowale

Ojabowale Afolabi is the content marketing lead at Heroshe. I have a deep passion for telling brands' stories to educate their audiences across a breadth of media and content forms.