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50 Funny But Tragic Valentine’s Day Fails To Make You Laugh Through Tears (New Pics)

50 Funny But Tragic Valentine’s Day Fails To Make You Laugh Through Tears (New Pics)

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Ah, Valentine’s Day! It’s supposed to be the most romantic day of the year. And for many people, it potentially is. However, it would be naive to think that everyone feels happiness, love, and passion on February 14. Far from it! Rejection is something that doesn’t take any time off, and it can sting even more than usual when it happens on this day. Nor do all your dreams come true when you like someone very much.
Our team at Bored Panda is featuring some of the most hilarious and tragic Valentine’s Day fails that have ever happened to anyone. These pics might not make your heart skip a beat, but they’ll likely hit you right in your meow-meow. Scroll down for a good dose of laughter through tears, a bit of secondhand sadness, and a reminder that even the best-laid plans can go awry.
Bored Panda wanted to learn how we can all handle rejection better, as well as how to show our partners that we appreciate them throughout the year, not just on Valentine's Day. We got in touch with Glenn Geher, Ph.D., who was kind enough to answer our questions. Dr. Geher is a professor of psychology at the State University of New York at New Paltz and a published author.

#21 To Roast Someone On Valentine's Day

Twitter conversation showing a humorous Valentine's Day fail involving comments about "my mum" and "your mum."
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51points

Younger generations plan to spend a lot more money on Valentine’s Day than older ones. Statista reports that in 2025, Americans from Generation Z are spending an average of $235 on February 14-related gifts and services. In second place are millennials who are spending roughly $176. Meanwhile, Generation X is spending just $95 while baby boomers are prepared to shell out an average of $53.

This makes sense the more you think about it. On the one hand, younger people are either still looking for love or they’re freshly in new relationships, so they want to leave a good impression with their gifts. On the other hand, members of older generations might increasingly value gifts that don’t necessarily require spending much money.

#22 Happy Valentine

Broken car window with rose petals, a knocked-over cup, and glass shards inside, illustrating a Valentine's Day fail.
My girlfriend left a gift in the car for me yesterday to find this morning when I went to work, but instead, I found a smashed window.
49points

#23 I Levo This Girl So Much

Woman surprised at Valentines-Day-Fails with hearts spelling "LEVO" on a checkered towel in kitchen.
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48points

#24 Sounds Like Jodee Should Get A New Valentine. Maybe Someone Who Doesn’t Cheat And Can Spell Slept

Car decorated with humorous signs for Valentine's Day fails.
48points

You don’t necessarily have to break the bank to celebrate Valentine’s Day in style. If you’re on a tight budget, you can surprise your partner with a handmade gift, a home-cooked meal, an awesomely romantic date, a song you’ve written for them, a painting you made, etc.

The sky and your imagination are the limit! What truly matters is that you give your partner the attention they deserve and find small ways to do something truly special for them. It’s not the price tag of a luxury gift that makes someone feel seen, loved, and understood. Your effort, on the other hand, is priceless!

#25 I Invited Friends And Family To A Art & Spirits (Drinking) Get Together At Home, I Was Planning On Painting Valentine's Day-Themed Pictures But Nobody Showed

Living room with empty chairs, table set for guests; Valentine's Day fails evident in lack of celebration or decor.
48points

#26 Valentines Pizza

Heart-shaped pizza in a box, representing a humorous Valentine's Day fail.
47points

#27 Valentine’s Day Rose Expectations. This Bouquet Feels More Like A Threat Or A Warning Than A Sweet Gesture. There Goes $110 Down The Drain

Black and pink roses arranged awkwardly, highlighting a Valentine's Day fail with mismatched flower hues.
43points

Have you ever had any Valentine’s Day fails of this caliber? How do you plan to celebrate Valentine’s Day this year, dear Pandas? Do you have any romantic or wholesome traditions with your partner?

Do you enjoy the holiday? Do you find it a bit cheesy and celebrate it ironically? Or do you try to find ways to be romantic throughout the year, whether or not it’s February 14? We’d love to hear all about your plans, expectations, and past rejections, so if you’ve got a moment, feel free to share yours in the comments!

#28 Found The Day After Valentine's Day

A large teddy bear stuffed in a green dumpster, illustrating a Valentine's Day fail.
43points

#29 Sorry My Friend Made This Ad, Nobody At The Company Knew What It Meant LOL

Dogs meeting with "Give and Receive" offer; humorous Valentine's Day fails apology from BarkShop.
42points

#30 This Heart Shaped Pizza Crust Again Highlights My Amazing Cooking Abilities

Heart-shaped dough on a griddle, a comical Valentine's Day fail in baking attempts.
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42points

#31 Flowers I Ordered For Valentines. Never Buy From 1800flowers Learned My Lesson After Reading How Much Of A Scammer They Are

Expectation vs reality of a flower bouquet, illustrating Valentine's Day fails with mismatched rose arrangements.
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42points

#32 What I Paid For vs. What They Delivered To My Wife For Valentines

Side-by-side comparison of Valentine's Day fails, with a vibrant floral bouquet on the left and a sparse arrangement on the right.
All she wanted were some flowers. A $50 arrangement with an additional surprise $30 service fee... What a scam. They wouldn't give me a refund unless I drove to the city she works in to return them.
41points

#33 Squirrels Infiltrated My Room And Stole My Valentines Chocolate While I Was Asleep

Valentine's Day fails: chewed chocolate wrapper and torn blinds, creating an unexpected mess.
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41points

#34 You Know It's Valentines Day When All The Ladies Razors Are Sold Out

Empty store shelves on Valentine's Day, indicating shopping fails.
40points

#35 Ordered Pizzas For Valentines Day With My Boyfriend And They Were Delivered Like This

Pizzas with toppings stuck to boxes, illustrating Valentines Day fails in food preparation.
The driver must've crashed and rolled their car like 40 times and still said "well I've got pizzas to deliver on we go" or someone got pissed that they work a job and was scheduled on valentines and just decided to ruin our day. valentines grinch or accident, I'm upset.

Good news though, we called the company & showed them these photos and they offered to send us new pizzas for free so our day isn't ruined. I'm putting these in the fridge for when I feel like a depression meal.
40points

#36 This Is How Men Will Embarrass You

Tweet about Valentine's Day fails at a comedy show, highlighting an awkward moment during a date.
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40points

#37 Bought A Single $4 Rose To Brighten Up My Desk For Valentine's Day, And Tried To Remove The Inexplicable Tag

Broken rose stem on a table next to a label, symbolizing Valentine's Day fails.
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39points

#38 An Attempt To Make A Romantic Valentines' Dinner

Heart-shaped pasta with pink sauce on a plate, illustrating Valentine's Day cooking fails.
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39points

#39 The Valentine's Day Brownies I Bought Expire Before Valentine's Day

Valentine brownies with expired date label, reflecting classic Valentines Day fails in product packaging.
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38points

#40 Valentine's Pastry At My Local Coffee Shop

Valentines Day fails: a glamorous dessert compared to a messy, underwhelming replica.
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37points
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