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!

5. Yankee Stadium Set-Up

Talking of pranks, here’s one which was on both the proposer and the proposee. It was set up by Amir Blumenfeld, of College Humor,  as part of his ongoing “Prank Wars” with his friend Streeter. At the cost of $500, you’d hope he finds it funny.
What happened was this - Streeter and his girlfriend Sharon was at a Mariners game at the Yankee Stadium, when a message popped up on the screen asking Sharon to marry “Streety Bird”. Streeter instantly got up, protesting his innocence and saying he didn’t do it, while Sharon looked confused. She said yes before he blurted out “I don’t wanna f***ing marry you!”. At which point she slapped him.
Meanwhile, across the stadium, Streeter’s “friend” Amir was commentating on the scene unravelling, ready to post up on collegehumor. Somehow a proposal that managed to embarass nearly everyone involved without the main participants having any idea what was happening. Remarkably, Streeter and Sharon were still together when last reported and even more remarkably Streeter and Amir are still friends.

4. Laguna Beached

There’s more romance down at Laguna Beach where Matthew Hartman chose to propose to his girlfriend Lis on a poster-worthy spot – a rock just out to sea. It looked beautiful, with Matthew dressed in a dark suit. And then a wave came and swept them both off the rock, into the sea.
By the time they’d staggered back to the beach, the moment had passed apparently. It might have been the laughing crowd that spoilt the romantic atmosphere or the wet-dog look they were both sporting. But happily she said yes anyway. And equally happily, he’d hired a professional photographer to capture the whole thing.

3. Minnesota Mishap

Next is another baseball-related one that sadly wasn’t any kind of a joke. During a Minnesota Twins game, a man decided to propose to his girlfriend via the big screen bit when the moment came she responded with a slap. Yes, it’s an eerie echo of the Yankee Stadium prank, but the funny thing about this one is that she looks delighted at first, before getting angry and slapping him. What did he do wrong in those few seconds? Answers below if you know, please…!

2. Awkwardness on the Almost Late Show

It’s live TV again and – as already proven – proposing on film is a risky proposition. Not only is there the possibility of her saying no, there’s also an audience of millions watching. That didn’t deter romantic Mike from proposing on the Almost Late Show with Bobby Bones, but it really should have.
The TV show – on METV – cued up some “love music” and Bobby asked Mike to the stage, complete with tiny pointy beard. He’d been with Lynne for a few months and as he crossed the floor towards her, there was a distinctly worried look on her face as if she knew something slightly awkward was about to happen. Mike went down on one knee, held the ring out and what was her response? “Can we talk about this later?”
Now, I believe that dead air in broadcasting is a bad thing – you never want several seconds of silence. But that’s just what happened as Mike, Bobby and the studio audience contemplated what had just happened. Luckily, musical sidekick Michael was on hand with a little demo music from his Yamaha keyboard to break the silence and ease the show into a much-needed commercial break…

1. Left Waiting in the Food Court

This has all the hallmarks of a classic proposal – a significant location, a relevant song, a big romantic gesture. It’ll be one to tell the grandkids.
Except there won’t be any grandkids. Cause she said no.
Let’s rewind a bit. The setting is a Westfield shopping mall – possibly in LA- in the food court, just outside Cinnabon. It’s where this guy met his girlfriend Caroline a year ago and he’s returned there to ask for her hand in marriage. Awww…
He starts making a speech. We’ve already seen how painful it is to get rejected after a long speech, so if you were watching this, you’d have your fingers tightly crossed for a good result and there are a LOT of people watching this.
Then there’s the song – “Sweet Caroline”. Ahh, he chose it especially for her. As the song builds towards the chorus, everyone in the food court joins in. It’s like a movie. They are all rooting for him. He gets down on one knee. And then she’s off. Out of the food court, out of the mall and -you’d assume – out of his life forever. A heartbreaking and humiliating proposal and a deserving winner of our #1 spot.