Cupid’s Biggest Mistakes Throughout History

It’s gotta be hard being Cupid.  The pudgy little diaper-clad god has to fly all around the world making people fall in love.   It’s a lot of responsibility … So, it isn’t surprising that Cupid’s made a few epic mistakes.

Here are the top ten Cupid fails from past and present.

Samson & Delilah

When love leads to hair loss and burnt-out eye sockets, you know Cupid screwed the pooch.

Jersey Shore’s Ron & Sam

Ron and Sam are the quintessential reality TV train-wreck couple – predictably dysfunctional.   Why couldn’t Cupid have given Sam’s post-MTV life a chance and made her fall in love with a pre-med Princeton legacy instead of the obvious juicehead.   Way to be lazy, Cupid.

Oscar Wilde & Lord Alfred Douglas

If Oscar Wilde had found someone less prominent than the son of the Marquess of Queensberry to lust after, he probably could have avoided that whole going to prison for “gross indecency” thing.  If only Cupid had swayed Oscar to fall for the pool boy instead…

Wilmer Valderrama & Everyone

Something’s amiss here.  Wilmer’s scorecard includes Mila Kunis, Jennifer Love Hewitt, Lindsay Lohan, Scarlett Johansson, Demi Lovato, and more.  It doesn’t add up.  Hmmm… Sure seems like Cupid does a whole lot of favors for Fez.  What’s the story, Cupid?  Are you just that much of a That ’70s Show fan?

Adolf Hitler and Eva Braun

Way to eff up history, Cupid!  You have the Führer in your crosshairs.  You have a quiver full of arrows.  Instead of shooting to kill.. .you shoot to make Adolf Hitler fall in love?  Major missed opportunity.

Kim Kardashian & Kris Humphries

Maybe this one isn’t Cupid’s fault.  Maybe the love god had nothing to do with Kim and Kris.   Maybe some reality TV executive’s arrow of profit-love was behind this short-lived match. We won’t throw Cupid under the bus for this one, after all.

Vlad “The Impaler” III & Jusztina Szilagyi

When the upshot of your union is vampirism and a whole lotta bloodshed, you can probably blame ol’ Cupid… Oh well.  At least Cupid didn’t hook Vladdy up with Bella Swan.

Lady Gaga & Taylor Kinney

Geez, Cupid.  Don’t you know that Lady Gaga shouldn’t be tied down… to anyone?  Keep your arrows away from Mother Monster.  The whole world is in love with her.

Vincent Van Gogh & That Prostitute He Gave His Severed Ear To

You know Cupid f*cked up when someone loses an ear.  Cupid could have done Vincent a solid and hooked him up with a sexy mental health professional.   Instead, Cupid made the painter jones for booze and the local filles de joie.  Very ear-responsible, Cupid.

Doug Hutchison & Courtney Stodden

WTF, Cupid?  We can’t even… It’s just… W… T… F…


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About the author

Kristen Bobst is a grade-A comedy writer, an unstoppable sock puppeteer, and the world's foremost whimsy aficionado. She certainly believes the meaning of life really is 42; and right now Kristen is really into The Carrie Diaries. Comediva. Where the funny girls are.

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