21 Hilariously Awkward Celebrity Prom Pictures

21 Hilariously Awkward Celebrity Prom Pictures

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We all remember the stress of Prom – the fear that somebody will show up in the same dress as you, what dress to get in the first place, the perfect hair to match the perfect dress, how many accessories are too many accessories or if your crush will ask you out. We’ve all been there.


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Or, if you’re the guy… well… it all seems a whole lot easier, actually. But still.

Either way it’s reassuring to know that even our favourite celebrities, who we see as flawless twenty-four-seven, also had their fare share of cringe-worthy prom pictures. So let’s celebrate that, shall we?

1. Jessica Alba

That’s a whole lot of flowers in one picture – and the classic pose, love it!

2. Danielle Fishell and Lance Bass

Let’s be real here – love the dress, one hundred percent would wear that now! But the awkward embrace is something else entirely! His one hand isn’t even touching her – it’s just awkwardly hovering. Maybe her dad was taking he picture.

3. John Krasinski

The patterns… So many patterns.

4. Matthew McConaughey

While I fully support the color-coordination, I’m not too sure about that big ole’ ruffled torso…

5. Will Ferrell

I really hope he won Prom Queen!

6. Britney Spears

While we can all admit that Britney was looking stunning as per, maybe she could’ve gone for a more striking pose? Or a pose at all, really.

7. Tupac Shakur

This prom photo holds an air of elegance and grace, and we really wanted it to be cringe-worthy… But in all honesty, it’s not your traditional style of prom-cringe – there’s still something awkward about the whole thing though.

8. Jimmy Fallon

Baby faced Jimmy sums up your average prom lad!

9. Jennifer Aniston

I always just pictured it as the prom from that one episode of Friends..

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10. Taylor Lautner

Meanwhile Lautner still has his beautiful baby face! The hair has definitely improved, though.

11. Lizzie Caplan

Speaking of hair… We almost didn’t notice the cow-print suit.

12. Jon Hamm

At least he looks like he’s having a blast.

13. Lucy Hale

Now a mermaid-style dress is one thing, but a dress that actually looks like a mermaid’s tail is another.

14. Angelina Jolie

Classically beautiful, no surprise there. I think she is the only one who would be able to pull of an actual no makeup look at prom, and a smile like that.

15. Blake Lively

The pink glittery dress and the tiara and blonde hair makes Blake every bit of the Barbie doll in every High School stereotype. But yet again, she manages to pull it off.

16. Brad Pitt

It looks like this could easily be his wedding pictures!

17. Sylvester Stallone

Why did the beehive go out of fashion?

18. Ellen DeGeneres

I almost don’t believe it’s real.

19. John Stamos

Matching colours with your date is overrated anyway – match hairstyles instead.

20. Barack Obama

Absolute legend from the get-go.

21. Taylor Swift



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Nobody here is surprised by this one.

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