The 20 Biggest Cringe Worthy Proposal Fails

proposal fails
With Valentines Day on the horizon, you may be thinking it’s time to trap your significant other into the conventions of marriage, where a legally binding contract can represent the love you share. It’s the natural way of things. Anyways, take heart from the 20 Biggest Proposal Fails, it’s not like it could go any worse than this.

Nice Toss

Apparently linking feelings of horrible loss with subsequent elation is totally kosher so long as you have a ring to back you up. I can think of about twenty ways this could have gone terribly wrong though, namely actually killing yourself by falling off a four story building.

Baltimore Police Raid
baltimore police raid proposal
So this joker though it would be a great idea to have a faux police raid occur while him and his girlfriend were relaxing on their private boat. When the “raid” took place, the cops searched through their belongings like there was enough blow on the dinghy to make Pablo Escobar blush. While contemplating her future in a women’s correctional facility, the cops produced the ring that was hidden all along, and the proposal took place. The good news is she said yes, the bad news is the city was none too pleased resources from the local police force (including a freaking helicopter) had been used for a private stunt.


I’d say that was a bit unnecessary, although I suppose he should be glad she didn’t throw a plate of scalding nacho cheese in his face.

In Russia, Proposal Makes You
fake death russian proposal

Once again, the whole I’m dead…just kidding scenario takes place here. What better way to express your love to your girlfriend than to stage a car accident, and have a paramedic inform her that you’re dead, only to jump out covered in fake blood and bandages to surprise her. She shockingly said yes after being put through this entire fiasco, which has set up an irony of epic proportions should he actually be killed in a car accident some day.

Tears of Joy…I Mean Terror

How quickly did it take him to realize those weren’t sobs of happiness? Probably not quickly enough.

tattoo proposal

Somewhere is a lonely tramp stamp that just says f@#k no.

Go Bruins!

Rumor has it that this was a staged failure by a group of comedians/actors. That may be true, but it’s epic enough in it’s humiliation level that I’m gonna give it the green light.

china electrocuted proposal

Yeesh, this poor shmoe climbed on to some power lines to hang a message of love to his girlfriend. He was badly burned, but survived, only to face a rejection from the object of his affection. Think you had a bad day, no, no you didn’t. This was a bad day.

Sweet Caroline

Oh, I get it, her name is Caroline. Maybe she wouldn’t have rejected you if you’d bothered to be a bit more creative, you know, as in not doing it in front of the local Cinnabon. Also, what the hell were you talking about with the cupcake thing? That’s why you want to get married?

Pass on the fail!

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Aqua Man
scuba proposal

“Join me in Atlantis, where we can spend the rest of our days in a paradise beneath the sea!”

Two Weeks?

I don’t really know why leap year came into this decision, nor do I really comprehend why your brotastic friends started chanting “four more years.” All I gathered is you’re somewhat unstable.

Over The Edge
fall of a cliff proposal

Taking your main squeeze on a hike through the mountains seems like a nice place to pop the question, if you’re one of those granola types I suppose. That all depends on her ability to not fall off a cliff however. When she regained consciousness, she said yes, so this story has a happy ending. That ride in the Medevac chopper must have been a beautiful thing.

Cheaters Never Prosper

Prior to this whole crazy sing for your love deal, it was revealed that Mr. Romantic was unfaithful, and he thought this would be the way to patch things up. Apparently that arrangement was not too good to pass up.

Splash Mountain
splash mountain proposal

Big points for coordination during a free fall, deductions for capturing your girlfriends face melting in the process.

Really, A Wizards Game?

I’ll say it again, a Wizards game? You deserved this.

Be sure to check out more Valentine Funny Photos.

God You’re Dumb
Merry Me Proposal Fail

I’m assuming you have the worlds largest penis, because otherwise no one would put up with your company.


This is actually a pretty good way to tell someone no, just pretend like you’re not listening.

I Love You Zoubek
upside down proposal sign

Is there some kind of inverted dyslexia I’m not aware of?

Rocket O’ Love

Somehow the bear’s frozen expression is perfect for consoling a rejected suitor and chastising a fleeing woman.

No Subtitles Necessary

Oh man, this one never had a chance. Can’t really imagine a worse audience to witness this than stands full of drunken hooligans either.

I’ll Also Have A 12 Piece

First class all the way.

Pass on the fail!

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