Top 10 Embarrassing Marriage Proposals

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.

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