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

Image credits: sicchic75

#2 Someone’s Valentine’s Day Didn’t Go To Plan At London Victoria

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

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#4 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?

Image credits: EclecticSpider710

#5 At Least She Tried… Happy Valentine’s Day

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#6 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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#7 Pizza Roses For Valentine’s Day – Looks Simple Enough… Let’s Blame It On Not Having A Cupcake Tray

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#8 Valentine’s Day Biscuits From Bojangles

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#9 How Romantic

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

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#11 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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#12 Rose Crepe Cake For Valentine’s Day

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#13 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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#14 Wife Got Perfume From Ulta Today, Pulled Out Her Valentine’s Day Gift In Spite

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

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#16 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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#17 Valentine’s Day Fail. Tried Making Heart Cookies For My Friend, Everyone Fails At Something

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#18 I Tried Making My Fiancé A D20 System Cake For Valentine’s

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#19 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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#20 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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#21 He Couldn’t See The Writing And Didn’t Laugh, Probably Because I Forgot He’s Color Blind

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#22 Valentine’s Delivery By TheBouqs Company. Expectation vs. Reality

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#23 Right On Track For Valentine’s Day  

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#24 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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#25 Chocolate-Covered Strawberry Fail. Pretty Sure They Are Not Supposed To Be Bumpy

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#26 A Very Important Question

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#27 For Valentine’s Day, We Tried To Nail It With Cakes  

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#28 My Boyfriend And I Tried To Make A Pink Cake For Valentine’s Day  

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#29 Someone Had A Rough Valentine’s Day

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#30 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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#31 That’s Valentine’s Day For You

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#32 Walked By This While Leaving Work… Someone Had A Bad Valentine’s Day

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#33 I Couldn’t Get A Real Man, And The Perfect Man Was Sold Out

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#34 Looks Like Someone Ran Out Of Money For The Skywriter Today

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

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#36 Valentine’s Day Is About Love, Right?

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#37 Happy Valentine’s Day

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#38 Valentine My Son Received At School Yesterday

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#39 So You’re Saying The Day Before Valentine’s Day Is Not A Good Day To Buy Your Kids Something  

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#40 Valentine’s Cupcakes That Are Best The Day Before Valentine’s Day

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#41 It’s A Good Thing He Loves Me Because My Cake Is Bad

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

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#43 The Flowers My Mom Received For Valentine’s Day

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#44 Selfie With My Valentine’s Date

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#45 When Valentine’s Day Didn’t Go As Planned

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#46 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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#47 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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#48 An Elegant Meal Prepared By My Girlfriend For Valentine’s Day

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#49 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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#50 Happy Valentine’s Day! I Will Never Bake Again

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#51 Dad Passed Away In August, And Mom Received This Today

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#52 Valentine’s Day Extraction Of Screws And Plate

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#53 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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#54 Okay, So Listen, You Would Think That Being An Artist, I Could Decorate A Cake Better Than This But I Spread The Icing While The Cake Was Still Warm

Then I forgot to put a decorating tip on the tube of writing icing. Valentine’s day and birthday fail for my better half.

Image credits: Ineffable_Panda

#55 Valentine’s Flowers For My Long-Distance Relationship Girlfriend Didn’t Get Delivered By The Florist

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#56 Somehow My Nice Valentine’s Gesture Looks More Like A Crime Scene

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#57 I Bought Flowers On ProFlowers For My Daughter For Valentine’s Day. They Arrived A Day Late And Were Mostly Dead

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#58 When Last-Minute Shopping For Valentine’s Day Goes Horribly Wrong

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#59 Valentine’s Day Gift On My Mom’s Car

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#60 So I Decided To Be Super Cute And Bake Cupcakes For My Significant Other And Then I Ate Them… Well Most Of Them Anyways

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

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#62 When The App Neglects To Flag That You’ve Run Out Of Characters

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#63 Not Only Do They Have A Troubled Love Category. It’s All Sold Out

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

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#65 Um, Ok Probably Not A Great Idea

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#66 This Valentine’s Day Candy Set Is Bananas

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#67 Pretty Sure That Half Of This Valentine’s Bamboo-Heart Plant At CVS Is Dead

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#68 I tried To Make A Cute Heart-Shaped Valentine’s Day Cake For My Husband. 3 Hours Of My Life I’ll Never Get Back

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#69 The Shrinkflation Going On With This Valentine’s Day Candy

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#70 Bought A Valentine’s Day Gift For My Daughter, Saw This When I Was Removing The Price Tag

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#71 Got These Warheads For Valentine’s Day. Did Not Have Any Black Cherry Whatsoever, 4 Lemons, And Watermelon Flavor Was Just Packaged Air

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#72 This Box Of Valentine’s Day Candy

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#73 Bad Valentine’s Day Edition

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#74 UPS Notifications Ruined My Valentine’s Day Flower Surprise

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#75 There’s Valentine’s Day Candy Out Already

Why can we not enjoy a holiday before the next one gets shoved down our throats?

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#76 Guess The Dough Wasn’t Frozen Enough For 11 Minutes In The Oven

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#77 The 1.25 Oz Jack Links Sasquatch Valentine. I Included A 1.45 Oz Hershey’s Kiss For Size Comparison. My Husband Was Very Sad

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#78 There Was An Attempt To Make My Crush My Valentine

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#79 Valentine’s Box Of Chocolate Is Missing A Whole Line Of Chocolate

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#80 I Know I Bought Mrs. S A Valentine’s Day Card, And I Know I Hid It In A Book, But Which Book? Is It Acceptable To Just Say It’s A Game Of Card Hide-And-Seek?

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#81 What Am I Going To Do With The 50 Packets Of Love Hearts That Arrived Too Late For The Workshop I Ran Yesterday?

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#82 Might Need To Provide More Direction The Next Time I Ask One Of The Boys To Put His Valentine’s Flowers In The Water

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

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#84 The Last Straw… I Hope This Company Gets Industry Blacklisted For Their Absolutely Abhorrent Reduction In Quality And Terrible Customer Service

Full hater mode at this point, wishing nothing but the worst.

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#85 Ordered A Nice Light-Up Ring Box For My Girlfriend To Go With A Ring I Got Her For Valentine’s Day. It Just Arrived, And When I Opened It Looked Like This

Took almost 2 weeks to arrive and the seller wants me to return the item before a refund is issued. Tried to see if I could salvage it myself but the hinges are snapped and it’s damn near impossible for me to fix.

Image credits: IveNoWIlly

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