Five Marriage Proposals That Are Worse Than Roy Williams'

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roy williams.jpg
Bet that's the last time Roy Williams goes to the post office.
For every mush fairy-tale engagement, there's a proposal gone wrong. Look at the Roy Williams proposal debacle, for instance. We're not sure what the Dallas Cowboys wide receiver was thinking when he mailed an engagement ring, along with a recorded proposal and $5000 for personal expenses, to his beauty-queen girlfriend, Brooke Daniels, but needless to say the proposal didn't go over so well with the former Miss Texas USA. She turned down his oh-so-romantic request for her hand, but she didn't return the $76,000 piece o' bling Williams sent.

Daniels claimed she lost the ring, so Williams filed a claim with his insurance company, which led to an investigation. The insurance company discovered the ring wasn't missing and that Daniels' father was in possession of it. Williams filed a lawsuit to reclaim the ring and asked for a restraining order to block the Daniels family from selling or destroying it.

A hearing to address the restraining order request was scheduled for Friday, but Michael Daniels, the ex's father, suddenly had a change of heart and has agreed to return the ring. It seems like Williams could have avoided this headache if he had asked for some advice on proposing. Sure, sending a ring and a proposal on tape is pretty bad, but not nearly as awful or embarrassing as these proposals. After the jump, see our picks for the worst ways to propose to your beloved.

5. Falling to one knee at the mall food court
Something tells us that having a friend sing "Sweet Caroline" to your girlfriend as you propose in front of the Cinnabon isn't going to get the response you're looking for. Commenters on YouTube claim the couple are actors, and we agree but it's still easy to imagine some dumb schmuck doing this.

4. Sneak attack in the friendly skies
Sure, she said yes, but she didn't look so thrilled to have her boyfriend pop the question in front of hundreds of strangers on a cramped Southwest flight. Plus, it's not like she can call her family or friends to share the happy news since she's on a plane. And hours from her destination.

3. Making the move at a sporting event
There are few women out there who are keen on the idea of being proposed to at a baseball or basketball game, so if you are planning on professing your love on the JumboTron make sure your partner is a die-hard sports fan who doesn't mind thousands of people seeing the proposal. If not, the next time Tracy McGrady laughs it might directed at you.

2. Performing a musical number on Disney World's Main Street
Why did she say yes? And where were Mickey, Minnie and Pluto? If you're going to choreograph your marriage proposal, don't high-five your dude-bro-musical buddies after she says yes.

1. Faking your own death
This seems like an obvious strategy to avoid, but then again so did the mail-in proposal. We're pretty sure this one is staged by actors, but if it isn't, this woman is in store for an early heart attack caused by her dumbass fiancé's antics.

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Oh yeah, that Disney proposal is fake, but it's a good example of how not to pop the question.

Noah W. Bailey
Noah W. Bailey

I've got a friend who proposed in this classic fashion:

His girlfriend was in the bathroom, putting on makeup and such.

He knocked on the door excitedly and yelled "hurry up--I gotta take a shit!"

When she opened the door, he was on one knee with the ring.

Amazingly, she said yes.


You are way off on No.1. While, as you noted, it appears to be staged by actors, the idea is genius!

This guy screws up twice. First, he hides the ring in a cake. Second, “Surprise! The wedding’s tomorrow.”

Elizabeth Bair
Elizabeth Bair

I wondered if that one was fake- I mean it's just terrible. No sane woman would accept that proposal.

Elizabeth Bair
Elizabeth Bair

That chick should have vomited on that d-bag just for putting her on a Style tv show. And jumping off a building and scaring the shit out of the woman you're trying to marry is still the worst way to go, Merten.

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