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Valentine’s Day might be one of the more stressful holidays, depending on your temperament and ability to plan. As most of us have learned from trial and error, planning and execution are often two very different things. 

So just to show that everyone has messed up on that crucial day, we’ve gathered some of the best and worst Valentine’s Day fails out there. From dates gone horribly wrong to the sad remains of someone’s idea of a gift, get comfortable as you scroll through, thank your lucky stars it wasn’t you and upvote your favorite examples. 

#1

A Very Important Question

A Very Important Question

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#2

I Made This For My Boyfriend For Valentine's Day But We Broke Up Yesterday So Here You Go Instead

I Made This For My Boyfriend For Valentine's Day But We Broke Up Yesterday So Here You Go Instead

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#3

Here's Something For You. Entertaining Valentine's Baking Fail. I Tried To Make My Husband A Cake For A Gift

Here's Something For You. Entertaining Valentine's Baking Fail. I Tried To Make My Husband A Cake For A Gift

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Rather confusingly, there were more than one Christian martyr named Valentine. Indeed, there are actually two Saint Valentine’s that are celebrated on February 14th, Valentine of Rome and Valentine of Terni. One of them (old records are not specific) was buried on February 14th, thus connecting this date to the name Valentine. 

You might be wondering, what exactly does the death and burial of a Christian martyr have to do with romantic love? As with so many holidays, this particular date ended up being conflated with an older, pagan celebration. The date and concept were kept, but the “star” of the show was not a Christian Saint, not the pagan Juno. 

#4

Valentine's Vasectomy

Valentine's Vasectomy

Getting the ol’ snippy snippy, I have anxiety issues and am quite nervous but committed, wish me luck!

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Tamra
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Get yourself a bag of frozen peas and some chocolates and champagne!

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#6

Invited 18 People To A Valentine's Day Poetry-Reading Party. Spent The Day Decorating And Getting Ready. 10 Said They Were Coming. No One Showed Up

Invited 18 People To A Valentine's Day Poetry-Reading Party. Spent The Day Decorating And Getting Ready. 10 Said They Were Coming. No One Showed Up

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Nina
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I really hat when people will say they'll come to something and just don't show up, especially when they don't excuse themselves

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The festival of Juno, Lupercalia, was celebrated on February 13–15th, so the “happy” coincidence of Valentine’s burial cemented the day's new name. The original celebration focused on love and fertility, so it was perhaps difficult to remove this association even if you were, nominally, celebrating a martyr. 

#7

Bought My Husband An Anatomical Chocolate Heart For Valentine's Day. He Thought It Was A Chocolate Ballsack

Bought My Husband An Anatomical Chocolate Heart For Valentine's Day. He Thought It Was A Chocolate Ballsack

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Nina
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Apparently he isn't that familiar with human anatomy, let alone his own..

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#8

In Honor Of Valentine's Day, Enjoy The Scary Cake I Made My Husband 10 Years Ago

In Honor Of Valentine's Day, Enjoy The Scary Cake I Made My Husband 10 Years Ago

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#9

Valentine’s Day Jam Drops: Taste 10/10, Presentation 4/10

Valentine’s Day Jam Drops: Taste 10/10, Presentation 4/10

Still ate them, still loved them. Just called them “broken-heart biscuits” instead.

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HTakeover
Community Member
2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Couple of tips... use a recipe that doesn't spread much. Use a cookie cutter to keep the shape round and consistent. And place heart-shaped molds in the top to be removed after baking.

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Modern readers aren’t the only ones to notice this discrepancy. February 14th as we know it, only really took off in the 14th century, with Chaucer's poems about it. Two specific pieces, Parlement of Foules and Complaint of Man seem to have sparked off the whole craze, although scholars have noted that the traditions and conventions he writes about don’t seem to have had any basis in reality. 

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#11

I Tried To Take A Staff Valentine's Day Photo Where I Work In Florida. It Didn't Work Out As We Had Hoped

I Tried To Take A Staff Valentine's Day Photo Where I Work In Florida. It Didn't Work Out As We Had Hoped

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#12

On Valentine's Day, My Son Decided To Show Me His First Magic Trick: How To Make A Coin Disappear. One X-Ray Later, I Found It   

On Valentine's Day, My Son Decided To Show Me His First Magic Trick: How To Make A Coin Disappear. One X-Ray Later, I Found It   

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In other words, this entire tradition might be the figment of the imagination of a poet looking back at the older meanings of Valentine’s Day. So if you rank among the folks who had a big Valentine’s Day fail or you don’t like the holiday in general, perhaps it can help to recognize that the whole idea might be made up in the first place. 

#13

I Tried Making My Fiancé A D20 System Cake For Valentine's

I Tried Making My Fiancé A D20 System Cake For Valentine's

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#14

Found On My College Campus A Few Years Back, A Week After Valentine’s Day

Found On My College Campus A Few Years Back, A Week After Valentine’s Day

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Little Wonder
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'd have taken it home because I would have felt bad for it. Shut up, I am so too an adult.

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#15

Walked By This While Leaving Work... Someone Had A Bad Valentine’s Day

Walked By This While Leaving Work... Someone Had A Bad Valentine’s Day

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Another common and perhaps warranted criticism of Valentine’s Day might be the over-commercialization of the entire thing. In the US alone, 190 million Valentine’s cards are sent every single year. Unfortunately, we do not have an average success rate on these, but one suspects the number isn’t high. 

#16

Controller Cookies For My Boyfriend's Valentine's Day Gift

Controller Cookies For My Boyfriend's Valentine's Day Gift

Very tasty, "better-than-bakery sugar cookies" (from the Gluesticks blog, I believe) with simple powdered sugar & milk glaze. The fail here is my awful piping skills and sprinkle placement.

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Nina
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

For a second I thought they left the controllers in the oven and they melted 😅

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#17

This Was In The Mall At 7 PM On Valentine’s Day. A Line Outside Pandora For The Last-Minute “Oh No, I Forgot Valentine’s” Gift. Guys And Girls, Don’t Let This Be You

This Was In The Mall At 7 PM On Valentine’s Day. A Line Outside Pandora For The Last-Minute “Oh No, I Forgot Valentine’s” Gift. Guys And Girls, Don’t Let This Be You

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Natasha Arruda
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I don't understand this... I'd honestly have no problem waiting for the 15th to celebrate with half priced goodies. I'd rather save money or just do something small.

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#18

That Sad Moment When You Realize Your Milk Has A Valentine's Date But You Don't  

That Sad Moment When You Realize Your Milk Has A Valentine's Date But You Don't  

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#19

Valentine’s Day Gift On My Mom’s Car

Valentine’s Day Gift On My Mom’s Car

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#20

Pizza Roses For Valentine’s Day - Looks Simple Enough... Let’s Blame It On Not Having A Cupcake Tray

Pizza Roses For Valentine’s Day - Looks Simple Enough... Let’s Blame It On Not Having A Cupcake Tray

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#21

At Least She Tried… Happy Valentine’s Day

At Least She Tried… Happy Valentine’s Day

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Ivo H
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Let's go through the facts: strawberries are there; chocolate is there; chocolate amount is greater then expected. Verdict - still yummy, NOT a fail <3

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#22

Someone's Valentine's Day Didn't Go To Plan At London Victoria

Someone's Valentine's Day Didn't Go To Plan At London Victoria

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Madam Puddyfoot
Community Member
2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My sister works at a florist delivered roses to a guy who wanted to surprise his wife with a dozen roses. Put them on the dining room table, and when she got home - shredded roses everywhere-- the cats had destroyed the whole bouquet.

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#23

My Ex Left Flowers On My Windshield

My Ex Left Flowers On My Windshield

I dated this guy (23M) for 3 months and found out he was cheating. After I dumped him, for 2 months, he would show up at my house unannounced and tell my roommates he was "concerned about me and wanted to check up on me". Several months later, I had already moved on and started dating someone new. It was Valentine's Day and my current boyfriend and I woke up to flowers on my car.

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#24

Someone Had A Rough Valentine's Day

Someone Had A Rough Valentine's Day

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#25

I Couldn't Get A Real Man, And The Perfect Man Was Sold Out

I Couldn't Get A Real Man, And The Perfect Man Was Sold Out

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#26

For Your Information, Do Not Make Your Sweetheart A Trash-Panda Cookie, Place It Near A Candle, Then Leave The Ceiling Fan On

For Your Information, Do Not Make Your Sweetheart A Trash-Panda Cookie, Place It Near A Candle, Then Leave The Ceiling Fan On

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#27

Valentine's Delivery By TheBouqs Company. Expectation vs. Reality

Valentine's Delivery By TheBouqs Company. Expectation vs. Reality

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Nina
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

If they are in bloom it'll be a bit better, but that's not the bouquet on the left

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#28

Rose Crepe Cake For Valentine's Day

Rose Crepe Cake For Valentine's Day

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Mark
Community Member
2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

That’s why you don’t make a crepe cake, you just stuff it in your mouth with a glob of Nutella as soon as it comes of the pan

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#31

Wife Got Perfume From Ulta Today, Pulled Out Her Valentine’s Day Gift In Spite

Wife Got Perfume From Ulta Today, Pulled Out Her Valentine’s Day Gift In Spite

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Nina
Community Member
2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

What is Ulta? Why would she pull out her valentine's day gift in spite afterward?

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#32

When Last-Minute Shopping For Valentine's Day Goes Horribly Wrong

When Last-Minute Shopping For Valentine's Day Goes Horribly Wrong

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#33

Just Getting Ready To Cook Valentine’s Day Dinner And Opened The Block Of Cheese I Bought Today

Just Getting Ready To Cook Valentine’s Day Dinner And Opened The Block Of Cheese I Bought Today

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#34

Time To Open Up The Valentine’s Day Candy! Oh

Time To Open Up The Valentine’s Day Candy! Oh

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#35

My Partner's Valentine's Day Gift Was Delivered Like This

My Partner's Valentine's Day Gift Was Delivered Like This

Box is also dented a fair bit, but other than that, it’s alright. Still ridiculous to even happen in the first place. Did no one genuinely think doing this was a bad idea?

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Little Wonder
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Amazon does have an option to request a box, but clearly they need to make that option more obvious.

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#37

Right On Track For Valentine's Day  

Right On Track For Valentine's Day  

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#38

Valentine My Son Received At School Yesterday

Valentine My Son Received At School Yesterday

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#39

Valentine’s Day Biscuits From Bojangles

Valentine’s Day Biscuits From Bojangles

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#40

Valentine's Day Fail. Tried Making Heart Cookies For My Friend, Everyone Fails At Something

Valentine's Day Fail. Tried Making Heart Cookies For My Friend, Everyone Fails At Something

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Nae who and where
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Good effort, but chocolate chip cookies are a drop cookie....drop cookies really can't be shaped.

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#41

Dad Passed Away In August, And Mom Received This Today

Dad Passed Away In August, And Mom Received This Today

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#42

Thought I’d Get Some New Candles For Valentine’s Day… Apparently Yankee Candle Can’t Ship Candles And Won’t Issue Replacements

Thought I’d Get Some New Candles For Valentine’s Day… Apparently Yankee Candle Can’t Ship Candles And Won’t Issue Replacements

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Lee
Community Member
2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

This is is a perfect example of using Twitter to put a company, in this case Yankee Candles 'on blast' (Am I using that right kids?)

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#43

Chocolate-Covered Strawberry Fail. Pretty Sure They Are Not Supposed To Be Bumpy

Chocolate-Covered Strawberry Fail. Pretty Sure They Are Not Supposed To Be Bumpy

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#44

When The App Neglects To Flag That You've Run Out Of Characters

When The App Neglects To Flag That You've Run Out Of Characters

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llama • she/her
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

why is the character limit so small when 'back' would absolutely fit on that cookie >:(

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#45

He Couldn’t See The Writing And Didn’t Laugh, Probably Because I Forgot He’s Color Blind

He Couldn’t See The Writing And Didn’t Laugh, Probably Because I Forgot He’s Color Blind

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#46

Thanks, ProFlowers, Only A Week Late And Like This. Flowers Were Supposed To Be Here On The 12th. They Shipped Late, And Then The Storm Hit. Customer Service Offered Me 20% Off

Thanks, ProFlowers, Only A Week Late And Like This. Flowers Were Supposed To Be Here On The 12th. They Shipped Late, And Then The Storm Hit. Customer Service Offered Me 20% Off

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#47

Happy Valentine's Day! I Will Never Bake Again

Happy Valentine's Day! I Will Never Bake Again

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Nae who and where
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I'm not even sure what I'm looking at....besides some oddly sliced strawberries

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#48

Happy Valentine’s Day

Happy Valentine’s Day

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Cat Chat
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2 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Wtf? "I don't like you THAT way.... but you still have to pay for me when we hang out". No... just, NO.

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#49

More From The Archives: A Valentine's Card Made By My Husband For His Mother

More From The Archives: A Valentine's Card Made By My Husband For His Mother

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#50

Our 4-Year-Old Wrote This On All Of Her Friends' Candy Bags In Pre-School Today And Told The Teacher It Said Happy Valentine's Day

Our 4-Year-Old Wrote This On All Of Her Friends' Candy Bags In Pre-School Today And Told The Teacher It Said Happy Valentine's Day

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