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7 Marriage Proposals That Went Very, Very Wrong …

Sometimes, things just don't go as planned. 

Digital Editorial Assistant
Photography by: dolgachov

From fake arrests to shutting down a major freeway, these proposals went above and beyond, but in a not-so-positive way. Consider these engagement stories a "what not to do when popping the question." Even though some of these guys had good intentions, life can be pretty unpredictable and things happened to go a little wrong. And remember: no matter how the actual proposal goes, getting that "yes" is all that really matters in the end.

Too-Public Proposal

A Reddit user proposed to his wife in Times Square on New Years Eve. "I was going for maximum cheezy," he explains. "She was pretty emotional and took a while to believe I was serious (even though I had a ring). This being New York, strangers started shouting at her to 'HURRY UP LADY, WHAT'S IT GONNA BE? WE DON'T HAVE ALL NIGHT!'" Classic New York City.


Interrupted in Dublin

Taking inspiration from the spirit of a city to propose is usually a good idea, depending on what city you're in. Dublin, for example, can prove to be "more difficult than it sounds because it's not a romantic city," explained a Reddit user. "After dinner, I decided that the Ha'penny Bridge was about the best place to get the job done. Right in the middle of my proposal, I hear the unmistakable sound of a drunk guy peeing off the bridge not ten feet behind me." If that didn't kill the mood, we don't know what would ... 

Highway Proposal

Vidal Valladares Navas, better known as "the idiot who shut down a major Houston highway for a marriage proposal" is now facing criminal chargers as a result of his romantic gesture. Navas originally told his girlfriend, and now-fiancée, Michelle Wycoff, that they were going to a friend's party. Apparently a specific spot along the freeway is one of Wycoff's favorite views of the city, so Navas got his friends to follow them for the drive, and then stop traffic while Navas got out of the car with Wycoff and down on one knee. Navas received a lot of backlash from the Internet and has since apologized for putting drivers in harm's way. "I just wanted to do something different," Navas told local news station KTRK after learning of the $5,000 fine for obstruction of a highway. "I never really thought about causing an accident, I thought about my girlfriend." We almost feel bad for the guy ... At least Wycoff said yes!


Pie To The Face

Another Reddit user, toast_n_gravy, gives the embarrassing details from his friend's engagement: "They were in a little French deli. She had just put a massive mouthful of pie in her face when she saw he had got[ten] down on one knee. She was so shocked she spat the pie out all over herself, all over him, all over everything," he explained. "She just sort of nodded ... It was very like her to do something like that so it's all fine but still ... I don't think he was expecting pie in his face."

A Fake Arrest

The best way to get a woman's attention is to fake an arrest, right? Kidding! But that's exactly what Matt Van Vliet did when he proposed to his now-fiancée, Samantha Labo. Labo and Van Vliet first met when they were arrested for underage drinking at a party during their freshman year at Colby College (they were both released later after passing a breathalyzer test), so when it came time for Van Vliet to pop the question, he reached out to the officer who arrested them. While on their way to dinner at their friends' house, the officer pulled them over, even though they weren't speeding. When Labo asked what was going on, the police officer responded with a rude remark. "I started crying because I didn't understand why he was being so mean," says Labo. The officer told Van Vliet he was under arrest, alarming Labo even more. As the police officer was handcuffing him, he gave him a pat down, pulling out a ring box. Van Vliet finally revealed it was all a ruse and walked over to the hysterically-crying Labo and asked her to marry him. The police car's dashboard cam captured the whole thing.


Tripped Up

Even proposing at a restaurant can have some unexpected consequences. While eating dinner at Applebee's, Reddit user jim_shorts witnessed a literally clumsy proposal: The guy kneeled down with his back leg sticking out into aisle of the restaurant. "He starts to propose when a waiter walks around the corner, trips over the bridegroom-to-be's outstretched leg and drops a tray of food, to which the waiter said, 'Sh*t, did I just ruin what I think I ruined?' In any case the girl ended up saying 'yes.'" 



We generally love a good hike engagement, but this one is a doozy. "A friend of mine was in a relationship for a very long time and they both knew that it was time to get married," explains Reddit user ippy116. "They had already discussed it before just not when he would ask and nothing was definite. They went hiking and were sitting on the edge of a cliff and all the sudden he gets down on one knee ready to ask her, but instead he stands back up and screams how he's too young for this and he can't do it and throws the box off of the cliff. She freaks out about how he just threw away the ring, then he gets back on one knee and takes the actual ring out of his pocket and says 'Just kidding lets get married.'" 

About the Author

Jane Asher

A total girly girl, Jane loves everything about the wedding-planning process, but her favorite part has to be where it all starts: the engagement ring. She's a sucker for all things sparkly, especially in diamond form and sitting on your ring finger. But she can't count out those gorgeous bridal bouquets. They may not be diamonds, but they still hold a serious wow factor. 


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