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
Image source: randomppl110
#2 I Made This For My Boyfriend For Valentine’s Day But We Broke Up Yesterday So Here You Go Instead
Image source: homomarijuana
#3 Here’s Something For You. Entertaining Valentine’s Baking Fail. I Tried To Make My Husband A Cake For A Gift
Image source: sicchic75
#4 Valentine’s Vasectomy
Getting the ol’ snippy snippy, I have anxiety issues and am quite nervous but committed, wish me luck!
Image source: mezzomike
#5 It’s A Good Thing He Loves Me Because My Cake Is Bad
Image source: brokenfencefarmsky
#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
Image source: holistic_ecofeminist
#7 Bought My Husband An Anatomical Chocolate Heart For Valentine’s Day. He Thought It Was A Chocolate Ballsack
Image source: jayneybee
#8 In Honor Of Valentine’s Day, Enjoy The Scary Cake I Made My Husband 10 Years Ago
Image source: FirstTimeMomics
#9 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 source: Safe-Lengthiness2636
#10 That’s Valentine’s Day For You
Image source: worldcompz, IamCatchvibe
#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
Image source: clevermine2tine
#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
Image source: Ordinary-Possession4
#13 I Tried Making My Fiancé A D20 System Cake For Valentine’s
Image source: StarLightDot
#14 Found On My College Campus A Few Years Back, A Week After Valentine’s Day
Image source: CDR57
#15 Walked By This While Leaving Work… Someone Had A Bad Valentine’s Day
Image source: reddit.com
#16 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 source: uwufren
#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
Image source: jamesdourney
#18 That Sad Moment When You Realize Your Milk Has A Valentine’s Date But You Don’t
Image source: Anonymous-Singh
#19 Valentine’s Day Gift On My Mom’s Car
Image source: evilek1
#20 Pizza Roses For Valentine’s Day – Looks Simple Enough… Let’s Blame It On Not Having A Cupcake Tray
Image source: stickyickyhippie
#21 At Least She Tried… Happy Valentine’s Day
Image source: DigitalLover
#22 Someone’s Valentine’s Day Didn’t Go To Plan At London Victoria
Image source: geozza
#23 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 source: frozen_reindeer
#24 Someone Had A Rough Valentine’s Day
Image source: penguine02
#25 I Couldn’t Get A Real Man, And The Perfect Man Was Sold Out
Image source: zombikittie
#26 For Your Information, Do Not Make Your Sweetheart A Trash-Panda Cookie, Place It Near A Candle, Then Leave The Ceiling Fan On
Image source: cakeandcork
#27 Valentine’s Delivery By TheBouqs Company. Expectation vs. Reality
Image source: Oh_helloooo
#28 Rose Crepe Cake For Valentine’s Day
Image source: JackofallCocktails
#29 How Romantic
Image source: cicithebawse
#30 Um, Ok Probably Not A Great Idea
Image source: tiffanydwhite
#31 Wife Got Perfume From Ulta Today, Pulled Out Her Valentine’s Day Gift In Spite
Image source: griswold0407
#32 When Last-Minute Shopping For Valentine’s Day Goes Horribly Wrong
Image source: da_vid.contreras
#33 Just Getting Ready To Cook Valentine’s Day Dinner And Opened The Block Of Cheese I Bought Today
Image source: Thea_From_Juilliard
#34 Time To Open Up The Valentine’s Day Candy! Oh
Image source: patorjk–
#35 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 source: EclecticSpider710
#36 When Valentine’s Day Didn’t Go As Planned
Image source: nycconcierge
#37 Right On Track For Valentine’s Day
Image source: Pg3_
#38 Valentine My Son Received At School Yesterday
Image source: ksigguy
#39 Valentine’s Day Biscuits From Bojangles
Image source: reddit.com
#40 Valentine’s Day Fail. Tried Making Heart Cookies For My Friend, Everyone Fails At Something
Image source: Emma_L0706
#41 Dad Passed Away In August, And Mom Received This Today
Image source: Myth_understood
#42 Thought I’d Get Some New Candles For Valentine’s Day… Apparently Yankee Candle Can’t Ship Candles And Won’t Issue Replacements
Image source: jallen50
#43 Chocolate-Covered Strawberry Fail. Pretty Sure They Are Not Supposed To Be Bumpy
Image source: jackmakesfour
#44 When The App Neglects To Flag That You’ve Run Out Of Characters
Image source: mo05hi
#45 He Couldn’t See The Writing And Didn’t Laugh, Probably Because I Forgot He’s Color Blind
Image source: MuschTender
#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
Image source: hank_cowdog
#47 Happy Valentine’s Day! I Will Never Bake Again
Image source: Saruei_
#48 Happy Valentine’s Day
Image source: MrMacgoot
#49 More From The Archives: A Valentine’s Card Made By My Husband For His Mother
Image source: GreenMachine1919
#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
Image source: highpointFL
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