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20 Awkward Celebrity Prom Pictures That Will Make You LOL

Prom season is in full swing and that means sparkly floor length gowns, box tuxedos, fancy updos, and inevitably cringe-worthy prom pictures. Thankfully, even our favorite stars aren't immune to the awkwardness that goes with prom. From Jessica Alba's Heidi-inspired prom dress to Adam Levine's all-white tux, these 20 celebrity prom looks are bound to make your sides hurt.

Michelle Obama

Michelle Obama

1 / 20

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Before she graced the cover of Vogue, our First Lady clearly went through some fashion—and furniture—don'ts. But check out that low-cut, high-slit dress! You go girl!

Photo: Splash Images

Will Ferrell

Will Ferrell

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Someone had a great sense of humor, even back in high school. Lookin' good in that tiara, Will.

Photo: Reddit

Ellen DeGeneres

Ellen DeGeneres

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Have you ever seen so much plaid? Even in 1976, this seems like too much.

Photo: Ellen DeGeneres

Wiz Khalifa

Wiz Khalifa

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Why so serious Wiz?

Photo: MTV

Usher

Usher

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Holy corsage! Usher really went all out. Perhaps he was making up for the fact that he did not coordinate with his date. At all.

Photo: MTV

Bruno Mars

Bruno Mars

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The "Uptown Funk" singer has always had an infectious smile, but we are really questioning that plant around his neck. Like, why?

Photo: Madame Noire

Adam Levine

Adam Levine

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Talk about looking washed out—the pair practically blends into their outfits! And we've got to talk about those coattails. Even for the '90s, what was Levine thinking?

Photo: MTV

Jessica Alba

Jessica Alba

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As dreadful as her dress may seem today, she was clearly very proud of it at the time.

Photo: izismile.com

Lizzy Caplan

Lizzy Caplan

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It's easy to see why Caplan was cast to play Janis Ian in Mean Girls.

Photo: Seth Poppel / Yearbook Library

Blake Lively

Blake Lively

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Would you look at those bangs? And that tiny tiara? Other than that, it doesn't look like she's aged a day. Not cool, Blake.

Photo: Imgur

Paul Rudd

Paul Rudd

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One word: Mullet.

Photo: Seth Poppel / Yearbook Library

Brad Pitt

Brad Pitt

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All white everything should really be reserved for your wedding.

Photo: Asos

Ashton Kutcher

Ashton Kutcher

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Kutcher has clearly always been the life of the party.

Photo: Seth Poppel / Yearbook Library

Ryan Seacrest

Ryan Seacrest

14 / 20

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That awkward hand placement is EVERYTHING.

Photo: Twitter

Snoop Dogg

Snoop Dogg

15 / 20

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Judging by the look on his face, prom just wasn't his thing.

Photo: Foul Gal

Tyra Banks

Tyra Banks

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Damn! Tyra knew how to strike a pose, even back in high school, but the awkwardly placed plant is what really makes this picture.

Photo: Fashion Style

Lady Gaga

Lady Gaga

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After seeing her in a meat suit, Gaga—Stefani, back then—looks surprisingly tame in this thin-strapped blue dress.

Photo: izismile.com

Nicole Polizzi (Snooki)

Nicole Polizzi (Snooki)

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Her date was really showing off his best tough guy 'tude. It didn't work.

Photo: MTV

Jimmy Fallon

Jimmy Fallon

19 / 20

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"My date went tanning that night," Fallon tweeted when he posted this picture to his Twitter. Either that or he was just trying to make up for the fact that he looked like a ghost.

Photo: Twitter

RuPaul

RuPaul

20 / 20

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We had to save the best for last. Even before he became one of the greatest drag queens in the world, RuPaul was already hard at work in high school.

Photo: RuPaul.com

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