'I went as Calvin and Hobbes... everyone thought I was Siegfried and Roy': 20+ Scarily awkward Halloween costume mixups

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Oct 25, 2024 3:00 PM EDT

Forgetting to wear a costume on Halloween can lead to people guessing your costume when you're not even wearing one! It's super awkward both for the guesser and the person who's just been sort of insulted by a random person. No one knows that more than the people who replied to u/MadmanPoet's question to the r/AskReddit community. They asked for the "most awkward Halloween Costume Guess you've ever gotten wrong," and told their own cringe-worthy story. They noticed a dude who wasn't wearing a costume, and mistakenly told him he looked like Tiger Woods. Awkward… because the dude was not dressed up at all! Yikes. 

Other people seem to have had similar experiences. One person thought someone was dressed up as Harry Potter. Nope! She was just a librarian wearing her normal work clothes. One person recounted a friend who absolutely loved his horse costume. However, people kept giving him the wrong compliment, telling him he looked just like the TV character Alf. He was super upset, even as he won a Halloween costume contest!  

Next up, read about this employee who was told that they were coming off as contemptuous towards their peers, so they just stopped talking entirely, leading to workplace calamity! 

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    Cheezburger Image 10419811328
    via Curated Lifestyle For Unsplash+

    This image is for illustration only, and the subjects are models; the image does not depict the actual subjects of the story.

  • 02
    What is most awkward "Halloween Costume Guess" you've ever gotten wrong. I'll start... Sooo, my office is letting us dress up today for Halloween (as we are closed on the actual Halloween). Well a few people dressed up, not many. But one
    via u/MadmanPoet
  • 03
    guy, a black guy, shows up in black pants and a red polo. I looked at him right as he walks into the office and say, "Dude! Great Tiger Woods!" He wasn't in costume. He was just a black dude in a polo shirt.
    via u/MadmanPoet
  • 04
    cboogie A buddy of mine, when he was maybe 5 or 6, really wanted to be a horse for Halloween. His mother and grandmother worked very hard on the costume. So the big day came and there was a costume contest at his school. He thought he had a good shot of winning. He
    via u/cboogie
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    was very proud of the costume. So who was the big winner? Everyone thought my buddy in the horse costume was Alf. He cried the whole time while collecting his prize.
    via u/cboogie
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    iced 1776 Wasn't me, but I was in an dorm elevator with a few other people and a girl looks over to a group of guys and goes "Oh are you guys going to the white trash party???" They weren't.
    via u/iced 1776
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    Treats I went as a teabag and everybody thought I was a bag of w d. After a while, I just went with it.
    via u/Treats
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    morph2k4 At a college Halloween party, my suite-mate's girlfriend was a sailor in white and blue. I asked her if she was the Pillsbury dough boy.
    via u/morph2k4
  • 09
    360walkaway Every year my girlfriend and I walk all over downtown taking pictures with random people in the costumes. One time I took a picture with a homeless guy thinking that he was a post-apocalyptic survivor. Ended up giving him $10 to iron out some of the awkwardness after.
    via u/360walkaway
  • 10
    pillbilly In 1986 (I was 9), the year Halley's Comet made an appearance, I dressed as Edmond Halley. Most people thought I was supposed to be George Washington. Obviously, I was one of the cool kids.
    via u/pillbilly
  • 11
    [deleted] When I was 12 I went as Britney spears version, my brother was a hobo and my friend a fairy. We went trick or treating and some lady answered the door and said, "Let me see, so we have a green thing. with wings, a hippie, and a ||
    via u/[deleted]
  • 12
    20 a This wasn't Halloween, but I once went to work and caught a glimpse of myself in the mirror. I was wearing a white short sleeved polo, very blue pants, and black dress shoes with a thick heel. That's when I realized I was dressed exactly like Homer Simpson.
    via u/adriannezy
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    [deleted] A friend planned a "trashy" themed pub crawl, where most people came wearing threadbare, crappy, thrift shop clothing. One dude came wearing Gucci shades, Sevens jeans, Ed Hardy shirt, the whole deal. I complimented him on his creative interpretation of "trashy." He was not in costume.
    via u/[deleted]
  • 14
    retsgip I was wearing a suit, a cape, a skull mask resting on the top of my head (not on my face), and holding a scythe. A girl walked by me and said, "OMG! Are you a HOBBIT!?" I'm short, but seriously? A hobbit?
    via u/retsgip
  • 15
    [ i didn't guess someone, someone guessed mine. She thought I was Robin hood A female Robin Hood I was Link I'm a guy.
    via u/[deleted]
  • 16
    corcor I was at a party when a guy in glasses wearing nothing but cut off jeans and green body paint walks by. Sort of like a green version of Tobias Funke in Blue Man Group paint. I stop and ask him if he is dressed as the Hulk. He looks at and says "No, the Hulk doesn't wear glasses". I reply "So what are you supposed to be?"
    via u/corcor
  • 17
    He then looks at me p ed "F YOU!" He walks away. My confusion leads me to go back up to him and ask what I did to offend him. He responds by shoving his hand in my face screaming at me to get away from him. I was so dumbfounded I didn't know how to react. I just walked away and I still don't know what he was dressed as.
    via u/corcor
  • 18
    limsee My best friend is a cute black girl. No matter what her costume is, the majority of guesses are "Beyonce?!".
    via u/limsee
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    TheCannon A pregnant Nun. She wasn't pregnant.
    via u/TheCannon
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    k A gay guy at work brought in a picture of him and his partner in superhero costumes. My guess... "So, you guys went as the Ambiguously Gay Duo?" Nope, Fantastic 4." I don't follow superheroes and I tried my best.
    via u/killawhaletank
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    [deleted] Last night my friend had a few too many drinks in him. Just as we're stepping outside to get some air, a young lady walks into the costume party. He stops and yells to me, "HOLY SHE'S HARRY POTTER. THAT'S AWESOME." He then
    via u/[deleted]
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    high fives her. She explained to us that she was not in costume. She was a piano teacher coming straight from work. She looked literally nothing like Harry Potter.
    via u/[deleted]
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    S My dad, with his beard, looked a lot like the Geico caveman. Before we made our way to a Halloween party at the local bar, he said maybe I should get a white t-shirt and write Geico on it and go as the caveman guy.
    via u/SportzTawk
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    He changed his mind, and said "Na, I won't dress up as anything." First step into the door and someone yells, "Dude! Look, it's the Geico caveman guy!!"
    via u/SportzTawk
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    [deleted] Drunken me: "What are you, a fairy or something?" Her: "I'M AN ANGEL!!"
    via u/[deleted]
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    [deleted] In this case, the costume was more awkward than the guesses... In third grade, I somehow convinced my mom to make me a Meep (from Commander Keen 3) costume. She was well aware that no one would have any idea what it was, and that this would make me upset, but I was insistent. I
    via u/[deleted]
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    wish I still had pictures, because it was pretty authentic-basically just a round green thing with a big mouth, but that's all a Meep is. Needless to say, my mom was right. "Frog" was the most common guess, which sort of ped me off, but I
    via u/[deleted]
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    got really angry when various adults managed to guess obscure characters that I also loved - "Slimer from Ghostbusters?" "a green Pac-man?" "Inky from Pac-man?" - that weren't right. Pretty sure my mom never made me a costume again.
    via u/[deleted]
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    [deleted] I guessed she was Pat from SNL. She actually wasn't wearing a costume.
    via u/[deleted]
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    xmashamm I dressed as a steampunk airship pilot. Went out in St. Louis. Everyone thought I had a phenomenal Charles Lindbergh costume. An old man sang a song to me about it.
    via u/xmashamm
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    CannibalSlang I went to a halloween party at a bar several years ago. I saw a man of considerable girth wearing a hawaiian shirt, a baseball cap, a moustache, and aviator shades. I proudly approached him, tapped his shoulder, and as he turned I declared, II John Candy!!!" Perfect
    via u/CannibalSlang
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    He just shouted, "I'M MAGNUM- A_H_LE" -P.I.,
    via u/CannibalSlang
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    [deleted] One year I went as Calvin and Hobbes. I had the black pants, the red t-shirt with horizonal black stripes, and a wig of messy blond hair. I even had a stuffed tiger to carry around. Everyone thought I was Sigfried and Roy. I retaliated, Calvin style, by making stupid faces every time a camera was pointed at me.
    via u/[deleted]
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    AnotherLoose... Me: Oh cool! A vampire! Her: I'm not dressed up for halloween
    via u/AnotherLooseSeal
  • 35
    avaryvox A walmart employee tapes. walmart bags over the entirety of her person. This random mash of oil, sweat and plastic was supposed to represent a "bag lady"... She asks me what I think her costume is and the first thing that comes out of my mouth is... "You're walmart trash."
    via u/avaryvox
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    It was awkward... because she didn't laugh and I simply squinted my eyes as close to shut as possible. PS- Clint Eastwood would have approved of my squinting skill.
    via u/avaryvox
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    notshawnvaug... Not sure if this counts, but we often did group costumes in college. Junior year, we decided to go as greek gods and goddesses (that was definitely our poorest year as a group). There were six girls and I was one of only two guys. that did it. my friend went as Zeus lightening bolts, - pretty easy. I could have been Poseidon, have a nice
    via u/notshawnvaughn
  • 38
    trident. Maybe go as Apollo, something to do with the Sun. Nope. I chose Hades. I thought I'd try to look like. Hades from Disney's Hercules. It was actually pretty close, but when you humanize a cartoon character with flaming blue hair, pale skin and dark eyes...turns out it's pretty gay (Not that there's anything wrong with that).
    via u/notshawnvaughn
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    One person that night recognized me as Hades. Everyone else, though...had a different interpretation. TL;DR Tried to pull off a Hades costume, and I was henceforth known as "Gay- des."
    via u/notshawnvaughn
  • 40
    rnjbond "Oh, you're a nurse!" "No... I just came back from volunteering at the hospital"
    via u/rnjbond
  • 41
    [ I dressed as a flapper. I dress pretty authentically vintage/retro what have you 40s/50s, every day, kinda my trademark. Everyone gave me all night for coming as myself and putting no effort in my costume. sigh "BUT GUYS YOU DON'T UNDERSTAND, THIS IS 1920S, THIS IS WAY DIFFERENT TO MY NORMAL
    via u/[deleted]
  • 42
    CLOTHES...GUYS? I ACTUALLY SPENT A LONG TIME GETTING THE CLOTHES AND DETAILS RIGHT" EDIT: First world problem or what? Broke my heart though. I spent way too long researching and sourcing the outfit.
    via u/[deleted]
  • 43
    marxychick1 Two years ago, I was Billy. Mays for Halloween. I took my daughter trick or treating with her 3 best friends and their parents. We stopped in at a party being thrown by another friend (the aunt of one of my daughter's friends). Her daughter answered the door, a girl I know well, and she let my
    via u/marxychick1
  • 44
    daughter and all of her friends in, and looked at me awkwardly and tried to close the door. She thought I was just some random guy trying to crash the party. I didn't know if I should be flattered or offended.
    via u/marxychick1
  • 45
    [deleted] My daughter's boyfriend came over and I said: "Great Edward!" Dude was dressed as Jacob. Daughter hasn't spoken to me in weeks.
    via u/[deleted]

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opinion costume ask reddit halloween costumes scary teens funny stories kids halloween spooky teenagers askreddit contest halloween costume funny opinions
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