Pumpkin with carved face, sharp teeth, and straw eyes, early Halloween fail.

30 Funny Halloween Fails That Didn’t Go According To Plan

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Halloween requires a level of crafting ability that I simply do not have. I can picture an incredible jack-o’-lantern in my head, but once I start cutting, we’re getting two triangles and a mouth. Maybe a tooth if things are going well. I know my limits.

Still, I respect anyone willing to put some effort into the holiday. Buying a costume online or attempting a Halloween-themed dessert should be relatively straightforward, but even those can lead to disappointment. Then there are the squirrels, who see your porch decorations as a seasonal buffet.

These funny Halloween fails are a reminder that you can plan everything and still end up with something worth photographing for entirely different reasons. At least when no trick-or-treaters stop by, you get to keep all the candy for yourself.

1. “All Of My Coworkers Agreed To Dress Up As Smurfs For Halloween. Im The Only One To Go Through With It”

Person dressed as a Smurf with blue face paint, white hair, and a white apron.
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2. “I Was Asked ‘Why Didn’t You Dress Up For Halloween?'”

Young woman with braided hair and serious expression in an office setting.
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3. “My Team Said We Were Dressing As Dominoes”

Group of six people dressed as dominoes and a pizza slice in an office.
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4. “Carved Our Pumpkin A Bit Too Early This Year”

Two carved Halloween pumpkins with scary faces, one with sharp teeth and the other with a menacing g.
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5. “Was At My Kid’s School For A Costume Parade. One Dad Misunderstood In The Best Way Possible”

People in line with a person in a T-Rex costume at a Halloween event.
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6. “Another Year, Another Pumpkin That Won’t Make It To Halloween Night”

A black dog with a pumpkin in its mouth on a porch during fall.
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7. “We Were Supposed To Go As Bikers But He Didn’t Get The Memo”

Two people in costumes, one in cycling gear, the other in a leather jacket and sunglasses.
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8. “My Contribution To Tomorrow’s Halloween Treats At Work”

Halloween strawberries with faces, showing expectation vs. reality.
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9. “This Pennywise Halloween Costume”

Child in clown costume with orange hair, white face paint, red nose, and striped pants.
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10. “Halloween Is Ruined”

Squirrel with its head inside a pumpkin, with a dog in the background.
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11. “I Ordered Some Tights For Halloween Online. I Didn’t Check The Size And It Turns Out They Were A Bit Too Small”

Person holding paper cutout of a bunny costume, with feet wearing bunny ears on bed.
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12. “Bought This For Our Halloween Family Skeleton Setup Because It Looks Exactly Like My Sweet Dachshund. She Unexpectedly Passed The Next Day”

Dog skeleton model on kitchen counter with a humorous Halloween theme.
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13. “Halloween Spider”

Hanging spider and a spooky black creature with glowing eyes on the wall.
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14. “Threw A Halloween Party On Monday. This Is The Only Picture Of Me, Because 20 Minutes Before Everyone Showed, I Got Hit With The Worst Food Poisoning I’ve Ever Had In My Life”

Person in pink dress with fishnet stockings holding a large cartoonish skull mask.
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15. “I Hit A Deer… While Dressed As A Deer. Happy Halloween”

Woman with reindeer antlers headband and dog with reindeer nose.
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16. “My Son Partied Too Hard At School Before Trick Or Treating”

Person in Pikachu costume sitting on a couch with a bag and slippers.
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17. “Hosted A Halloween Party And No One Showed Up”

Four Halloween-themed ribbons with funny labels on a wooden desk.
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18. “My Partner And I Tried To Make A Gingerbread Cat For Halloween I Think Ours Is Spookier”

Halloween skeleton horse cake with black body and colorful decorations.
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19. “October Thunderstorm, Before And After”

Two Halloween decorations: a glowing skeleton in a tattered sheet and a ghostly figure in a plastic.
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20. “I Wanted To Dress As ‘Cotton Candy’ For Halloween”

Person in pink costume with a large head and simple face, holding a bucket.
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21. “Two Women Let Their Dogs Pee And Jump On My Halloween Decorations. Then Let One Up On My Porch”

People and dogs near a large inflatable pumpkin with a witch hat during Halloween.
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22. “I Spent $200 On Full Size Candy To Be ‘That House’ For Halloween. Only Had One Group Of Trick Or Treaters Come By So Far And It’s Almost 9pm”

Colorful Halloween scene with candy and glowing lights in a room.
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23. “I Did Not Do The Research On When To Plant Pumpkin Seeds For Halloween (21 July)”

Pumpkin growing next to a large green leaf and a brick wall.
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24. “The Only Picture My Drunk Boyfriend Got Of My Halloween Costume”

Blurry image of a person with a Halloween mask and decorations.
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25. “Halloween Decoration My Mom Bought”

It's just a bunch of Houcs poucs with a witch hat in the middle.
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26. “How Many Years Bad Luck For Breaking My Bosses Hundred Year Old Mirror… In A Haunted Pub… On Halloween?”

Broken ornate wooden mirror with cracked glass in a vintage setting.
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27. “Got Appendicitis On Halloween. Luckily We Caught It Early Before It Perforated So I’m Here To Live Another Day”

Young man in hospital bed with medical equipment, caption says 'Er tiiiiime'.
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28. “Someone Ruined My Neighbour’s Kids’ Halloween Pumpkin They’ve Been Growing For Months And Months”

Pumpkin with a carved face and a sign about pumpkin growing.
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29. “Tried To Make A ‘Stab Wound’ For Halloween… And It Looks Like A Menstrual Pad”

A bandage with a fake blood stain, part of a Halloween fail.
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30. “Finally Have My Own Place And Bought Candy For Halloween Only Had 2 Kids Come By”

Halloween candy in a black skull and skeleton bowl on a kitchen counter.
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