10 Hilarious Engagement Fails That Prove Guys Don't Always Think Things Through


Did you see this guy who tried to perfectly propose to his girlfriend at a Yankees game last night? I say "tried" because he pulled out the ring, but then immediately dropped it. Yup.

With the help of the people around them, it took the couple an embarrassing five minutes to find the ring. I guess that's what you get when you plan the most overdone proposal of all time.

Engagement fails like this are hilarious AF. They make me feel better about my life (because I'm single AF, and the prospect of an engagement is very far away), and remind me that not everything goes as planned.

And hey, that may not necessarily be such a bad thing! Having a great story to tell your kids and grandkids — as embarrassing as it may be — is a million times better than going through the motions of your standard vanilla engagement that was on the top of a mountain, went off without a hitch, and "she said yes."

No offense, married folks, but those vanilla engagements suck.

We want the JUICY stories. The ones where a friggin' eagle comes out of nowhere and swoops that bling out of his hand, and you and your future hubby literally have to traverse 10 miles of the great outdoors before finding the bird's poop, which you then have to sift through bare-handed to get your diamond back.

Now THAT's a story.

Here are more hilarious engagement fails that reach that legendary status:

This guy whose girlfriend savagely rejected him:

JeromeInRealLife on YouTube

This guy who popped the question in a paddle boat (GREAT idea, Skipper):

Swilk 16 on YouTube

This guy who proposed with a McDonald's sandwich (WTF?):

Conditional Love on YouTube

This girl who SO wasn't ready for it:

This man who probably wanted to throw her overboard, too:

Inside Edition on YouTube

This guy who totally got OWNED by a tiny guitar:

NewsBomb on YouTube

This GIRL who had the worst idea ever and then WENT HAM on her BF:

partyingamigo on YouTube

This guy who was dumb enough to tie the ring to a balloon:

FAIL Blog on YouTube

This guy who got shot down on NATIONAL TV:

Simon Shipley on YouTube