The 14 Greatest Marriage Proposal FAILs of All Time

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There are few things more entertaining than the heart-wrenching misery of other people. Some of the greatest moments in cringeworthy Internet videos can be found within the hundreds of videos of people being denied a fair maiden's hand in marriage in some brutal, embarrassing, and public way. So, here are the best (worst?) videos of guys making terrible decisions with what's supposed to be one of the greatest moments of their life (leading to what is probably the worst moment of their life).

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  1. 14

    Guy's Proposal Goes Overboard

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    Romantic gestures are no match for open bodies of water. It's a lesson Wisconsinite Shane learned after trying to propose to his girlfriend on a paddle boat in the Wisconsin River. Shane prepped for the big event by inviting his girlfriend, Cheri, and a few friends onto the water. Once out there, he told Cheri to look over at the shore, where more friends stood with signs that said "Will you marry me?" Unfortunately, Cheri's excited answer caught Shane a little off-guard. During the proposal, she inadvertently knocked the ring out of Shane's shaking hands and into the water. The couple searched for two days, but couldn't find it. Lucky for Shane, Cheri agreed to get engaged anyway. Unluckily for Shane, he's got to shell out for another ring.

  2. 13

    Man Dresses as a Mascot, Asks GF at Half-Time

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    Nothing quite like turning your engagement into a giant half-time show. This game, apparently, is called "find the mascot while blindfolded."

    Having successfully found the mascot the young girl gets her prize, the Mascot deflates and out of its leathery skin walks her boyfriend, ready to propose.

    This winner, who looks like the kind of guy who actually uses a belt attachment for his cell phone, takes a knee and in an extremely insecure sounding voice says 'baby, baby, baby' while his now ex-girlfriend runs away.

    His biggest mistake? Nobody wants to marry a mascot.

    Special thanks to 2009's Keyboard Cat for providing us with musical stylings and playing the girl out of the stadium.

    The craziest part about some of these is that the girls don't just say no, they RUN out of wherever they are, like they're in danger. Judging by a lot of the guys on this list, though, maybe they are.

  3. 12

    News Reporter Botches Wedding Proposal Intro

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    Tip #1 for getting engaged: If you're an athlete (even if it's college level) don't let the news announcers know that you plan to propose to your girlfriend, especially if they work for Fox.

    After a victory for Boise University, Fox sent a reporter to talk to star player Ian Johnson. While Ian stands there with his girlfriend by his side, about to pop the question, the reporter says, as a transition, "... Now, I know you're going to propose to your girlfriend! Congratulations!".

    What a douche.

    Luckily, everything worked out fine when Ian dropped to his knee as his girlfriend excitedly yelled "Yes!"

    Star Football Player marries the Head Cheerleader? That's the type of Ultra-American happy ending that Fox lives for.

  4. 11

    Blowing in the Wind

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    This idea seemed sweet. After two years of being together our proposer decided to pop the question at the very park they went to on their first date. Furthermore, to recreate that first date, he got a heart-shaped balloon. He claims he got her the same balloon on that first date. Up until this point it's a pretty adorable engagement idea.... Until he begins to tie the ring to the balloon (I think you can see where this is going).

    His friend is filming from a distance and catches the entire scene.

    He walks up to her and hands her the balloon. They walk for a bit and then he takes a knee. In excitement she lets go of the balloon which promptly flies away and our suitor immediately starts yelling and chasing down the balloon. Why? Because it has the ring on it. How has this guy managed to live this long?

    Did she say yes? That's up for debate. Perhaps she realized how poorly thought out his proposal idea was and decided against sharing an income, home and family with him. Anyone would, really.

    This video seems almost too good to be true. Almost.

  5. 10

    Christmas Is The Time Of Denying

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    Everyone loves Christmas: the carols, the TV specials, the unbelievably painful, soul-crushing heartbreaks. It truly is the most wonderful time of the year.

    It's Christmas time for average family USA. Opening presents, drinking wine, celebrating happily; that is, until the daughter's scrawny boyfriend stands up and demands attention.

    He nervously thanks them for the invitation and hospitality. While he comes off a little dorky he seems like a genuinely good guy. Finally he pops the question and the family celebrates. Unfortunately for him, she was not in the Christmas spirit.

  6. 9

    So, Some People Apparently Have Morning Zoo Radio DJ's Ask For Them

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    To be fair, what kind of douche involves a morning zoo radio talk show host in their proposal? This guy had it coming.

    For a brief period in time there was a radio personality out in my hometown named Kidd Chris. He was a shock jock DJ who happened to be friends with Howard Stern. He would prank call celebrities and occasionally would invite listeners into the studio for a game called "Tennis Ball Trivia" where you'd get tennis balls fired at you for every wrong answer. He was funny, anarchic, and I was a loyal listener to his show. What I'm trying to say is that if the radio personality from this video "Nigel" was even half as outrageous as Kidd Chris; then this guy should have known better!

    This video stars a loyal listener who wants to surprise his girlfriend by having the morning drive radio DJ pop the question to his girlfriend for him. This already sounds like the worst proposal idea ever. The DJ agrees to do it, but only if the guy gives his girlfriend the phone and then leaves the room.

    Again, this would sound like a bad idea to any sane human being.

    Regardless, our lazy caller does exactly as Nigel requests. Nigel instead tells this girl that he's been cheating on her. I think it's reasonable that Nigel didn't expect her to hang up before he could fess up to the joke, but it seems like it's too late for what ifs when she ostensibly breaks the guy's cell phone.

  7. 8

    I Better Tell Her Not To Tape This

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    Australia, like every non-American country in the world, loves soccer (aka football) and rugby much more than the rest of us. They even have entire shows dedicated strictly to their love of Rugby and Football, including the award winning "The Footy Show" (now in it’s 18th Season).

    Despite Australia’s enthusiasm for rugby and football, I still think the average woman doesn’t want to be proposed to on what is basically a "SportCenter" and "Sabado Gigante" hybrid.

    But that doesn’t stop Peter, who goes up on stage and talks about his girlfriend Katherine, who he’s been with for three years. He drops on his knee to propose and she starts shaking her head. This is usually when you know the guy is f*cked. The saddest part is that he begins to beg her to say yes before she gets up and runs off the stage. This poor guy's only response: ‘I told my mom to record it... I better call Dad and make sure he doesn't record it.’

  8. 7

    Slapped In The Heart ... And Face

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    This video starts off adorably. It's a baseball game when this guy proposes to his girlfriend. The crowd starts cheering. But then around the 15-second mark, something goes terribly wrong. I don't know what the guy says, but his girlfriend immediately goes from joy to anger. Immediately she slaps this guy across the face and storms off. The entire surrounding crowd gasps and our proposer begins to cry.

    Aaand scene.

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