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Simona Kinderytė

People Share Their Worst Valentine’s Day Fails, Here Are The 85 Funniest Ones

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 A Very Important Question

Image credits: randomppl110

#3 Valentine's Vasectomy

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

Image credits: mezzomike

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

Image credits: CDR57

#5 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   

Image credits: Ordinary-Possession4

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

Image credits: homomarijuana

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

Image credits: geozza

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

Image credits: StarLightDot

#9 It's A Good Thing He Loves Me Because My Cake Is Bad

Image credits: brokenfencefarmsky

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. 

#10 That’s Valentine's Day For You

Image credits: worldcompz

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

Image credits: stickyickyhippie

#12 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

Image credits: holistic_ecofeminist

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 At Least She Tried… Happy Valentine’s Day

Image credits: DigitalLover

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

Image credits: clevermine2tine

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

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

Image credits: Safe-Lengthiness2636

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

Image credits: Thea_From_Juilliard

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

Image credits: reddit.com

#18 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

Image credits: jamesdourney

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

Image credits: evilek1

#20 Rose Crepe Cake For Valentine's Day

Image credits: JackofallCocktails

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

Image credits: jayneybee

#22 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

#23 Valentine’s Day Biscuits From Bojangles

Image credits: reddit.com

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

Image credits: patorjk--

#25 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.

Image credits: uwufren

#26 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.

Image credits: frozen_reindeer

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

Image credits: FirstTimeMomics

#28 Someone Had A Rough Valentine's Day

Image credits: penguine02

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

Image credits: cakeandcork

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

Image credits: zombikittie

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

Image credits: Oh_helloooo

#32 Right On Track For Valentine's Day  

Image credits: Pg3_

#33 How Romantic

Image credits: cicithebawse

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

Image credits: jallen50

#35 Um, Ok Probably Not A Great Idea

Image credits: tiffanydwhite

#36 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

Image credits: highpointFL

#37 Happy Valentine’s Day

Image credits: MrMacgoot

#38 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

Image credits: hank_cowdog

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

Image credits: mo05hi

#40 When Valentine's Day Didn't Go As Planned

Image credits: nycconcierge

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

Image credits: jackmakesfour

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

Image credits: Anonymous-Singh

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

Image credits: MuschTender

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

Image credits: Emma_L0706

#45 Valentine My Son Received At School Yesterday

Image credits: ksigguy

#46 Happy Valentine's Day! I Will Never Bake Again

Image credits: Saruei_

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

Image credits: Myth_understood

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

Image credits: GreenMachine1919

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

Image credits: puppymonkeybaby79

#50 My Boyfriend And I Tried To Make A Pink Cake For Valentine's Day  

Image credits: saturnzbirbs

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

Image credits: lazygayboredtrans

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

Image credits: _.ttonetown_la

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

Image credits: da_vid.contreras

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

Image credits: lindseytatumphotography

#55 Valentine's Day Extraction Of Screws And Plate

Image credits: cbennett_82888

#56 For Valentine's Day, We Tried To Nail It With Cakes  

Image credits: reddit.com

#57 Bad Valentine’s Day Edition

Image credits: jeanmariede

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

Image credits: sense_make

#59 Somehow My Nice Valentine's Gesture Looks More Like A Crime Scene

Image credits: lynncolepaugh

#60 Selfie With My Valentine's Date

Image credits: Britified

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

Image credits: danielle_despres

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

Image credits: LordLogan129

#63 Valentine's Day Is About Love, Right?

Image credits: pichael288

#64 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?

Image credits: nonperfectdad

#65 This Box Of Valentine's Day Candy

Image credits: OGWan_Ked00bi

#66 Valentine's Cupcakes That Are Best The Day Before Valentine's Day

Image credits: KaylsTheOptimist

#67 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

Image credits: Correao

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

Image credits: HymnElle

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

Image credits: griswold0407

#70 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

Image credits: Okiedokethen7

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

Image credits: Gretchen_NCH

#72 This Valentine’s Day Candy Set Is Bananas

Image credits: shanks__x2

#73 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

#74 Valentine's Box Of Chocolate Is Missing A Whole Line Of Chocolate

Image credits: ifugly

#75 The Shrinkflation Going On With This Valentine's Day Candy

Image credits: Beave1

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

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

Image credits: davidp1984

#78 An Elegant Meal Prepared By My Girlfriend For Valentine's Day

Image credits: croblyer

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

Image credits: Jess_Security

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

Image credits: meloiseb

#81 Guess The Dough Wasn't Frozen Enough For 11 Minutes In The Oven

Image credits: kendrick_not_lamar2

#82 The Flowers My Mom Received For Valentine's Day

Image credits: mommabear216

#83 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

#84 There's Valentine's Day Candy Out Already

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

Image credits: enslaved1

#85 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.

Image credits: Bitter_Ad_3976

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