Top 10 Embarrassing Marriage Proposals

The mood is right, the lights are dimmed, the Mariachi band has just struck up “Love Me Tender” and the girl of your dreams is sitting there, opposite you. Take a deep breath and….propose. If she says yes, you’re very lucky. If she lets you down gently, you’re still lucky. In fact, as long as she doesn’t reject you live on TV or in front of a crowd of booing people you’re doing pretty well. Imagine how wrong things could have gone. And if you can’t imagine it, take a look at the failed proposals we’ve gathered together in our Top 10 Embarrassing Marriage Proposals. You may want to hide behind a cushion for some of these…


10. Clumsiness on Brooklyn Bridge

Here’s a romantic setting for a proposal – the pedestrian walkway above Brooklyn Bridge, with views over New York and family members discreetly tucked away, filming the whole thing. But while the proposal was planned to the last detail, the one thing that Don Walling didn’t check was how big the gaps between the planks were, and whether a ring would fit through them.

Because that’s what happened. Don got down on one knee in front of girlfriend Gina Pellicani, opened the box and dropped the ring between the planks. His face (above) says it all. Losing no time, he climbed down the bridge onto the roadway below, triggering a suicide alert with local police, and retrieved the ring. Luckily she said yes, and they later went on the Today program to tell the world about it.


9. Embarassment at the Empire State Building

Another New York proposal, another disaster. There’s something about the New York landscape that obviously brings out the romantic in men and clearly the iconic building is the place to propose. There’s even a how-to guide on the subject.

But would-be proposers are advised to use some caution and not let the altitude go to their heads – like one man who videoed his proposal to girlfriend Bridget. As he said “I’ve got something to ask you” and went down on one knee, she responded with a spirited “What the f*** are you doing?” And she was serious. Guess that couple never had their Fairytale of New York Ending!


8. Sewer Searching in Denver

Good to know that Don Walling is not the only person to have a little problem holding on to a ring. When planning a proposal to his girlfriend Kaitlyn, John Iverson probably thought he was guaranteed success – after all, he had one of her family heirlooms to propose with – a ring belonging to her mother. And it was Valentines’ Day, the most romantic day of the year! So it was no surprise to him when she said yes. What a lovely, smooth proposal.

Oh, but there’s a hitch…as he went to put the ring on her finger, he fumbled it and dropped it down a storm drain. Into a sewer. Luckily, firefighters arrived and rescued it after a mere 45 minutes of sifting through human waste. Good result!


7. Jesus Jam Slam

This is another idea  that must have seemed like a great one at the time. A young man, in love with both his girlfriend and  Jesus decided to take the next step at an open-air meeting called the Jesus Jam. His girlfriend is brought on-stage and after a lengthy speech, he asks her to marry him. Cue an awkward pause while she considers her answer…and it’s a no. An apologetic head shake and she walks off-stage leaving him alone. And yes, it’s all on film. It’s even more painful because of the long speech he gives her before asking the question. If you’re going to get shot down in public, best to keep it snappy.


6. Framed on the Footy Show

Of course, you can’t believe everything you see on TV. Getting knocked back live on Australian TV seems like it would be most humiliating for the man involved, in this case Peter on the “Footy Show”. He asked his girlfriend Catherine to make him “the happiest man on Earth” and to “just say yes” but she looked panicked, embarrassed and finally ran off crying. The host shuffled round saying things like “Good on ya mate, it didn’t go that well but…” while Peter sobbed about how he’d told his mother to record it. Ouch.

Or is it? Turned out the joke was on host Paul Vautin, as the whole thing was a hoax for his 50th birthday. Those crazy Australians!

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