The 14 most awkward wedding proposals ever witnessed.

Image: Leap Year/Universal Pictures

In an ideal world, a marriage proposal would be highly romantic.

Unfortunately, life isn’t a Hollywood movie and things don’t always go to plan… and the whole thing can quickly become memorable for the all wrong reasons.

In a Reddit thread, users shared the most awkward proposals they’d ever witnessed or been told — and saying ‘no’ wasn’t even the most cringe-worthy outcome.

1. Wake me up when September ends

It doesn’t get much more awkward than user Fulcrum19’s father’s proposal.

“It just happened randomly:

Dad: ‘How much weight do you think you can lose by September?’

Mum: ‘Wait, what?’

Dad: ‘I was thinking we could have the wedding then.’

“He’s not known for having a lot of tact.”

WATCH: All the products behind Sofia Vergara’s wedding makeup look. (Post continues after video.)

2. It’s not what it looks like…

Tip: Be cautious when it comes to gifting jewellery.


“A guy I knew (a really stupid guy) got his girlfriend a diamond ring as a birthday present, not intending any larger message. She unwrapped it and said, ‘Oh! Of course I will!'” wrote postmodulator.

“He went through with it rather than deal with the awkwardnessDidn’t last.”

3. Burger ring

“I was in a fast food chain years back, and saw a guy propose to his girl by slipping the ring into the cheeseburger wrapper. It was the most depressing thing I have ever seen,” wrote one user.

4. Man in a uniform

This is probably the only time you’d want to be pulled over.

“I proposed to my wife using the police. I had her get pulled over and then they told her she was the suspect in a theft crime. She got all nervous and then the police officer pulled out a picture of me and told her, ‘You stole this man’s heart.’ Then I got out of the back of the cop car and dropped the knee. She liked it,” wrote CLEsportsfan. (Post continues after gallery.)

5. Life is a rollercoaster

Sometimes the idea is better than reality.

“So this is a true story… a guy wanted to propose to his girlfriend at Disney World. VERY common, usually in front of the castle, usually with staff involved for pictures and stuff and usually Disney will do what they can to make it special,” wrote UCMCoyote.

“But no, this genius, this man of men, decided he had to step it up a notch. Decides to do it on Splash Mountain. At the peak. Right before the drop. Aaaand he dropped the ring.”

6. Third wheel

User Madsusie became an unwilling participant in one couple’s special moment.


“I ruined some guy’s marriage proposal by mistake when I tripped and shoved past the two just as he was going down on one knee. He almost dropped the ring, and got p*ssed off at me.”

7. Don’t pull a Ross

“My mate did it in front of all his mates and called her by his ex’s name (and no this is not a Friends try hard comment). It was so embarrassing even I wanted to crawl into a hole and die,” wrote one contributer.

Err Ross, that's actually your fiance Emily. Image: Friends.


"I had a dude propose to a girl at the bowling alley I worked at. He made me bring the ring with the sh*tty bowling alley food they ordered. It was a crowded noisy awful night," wrote pokemongo.

"When I brought the ring over he said 'Oh, what is that? I didn't order that? Did you hun?'  Mind you he was drunk so his words were all slurred. She didn't seem to want to be there from the beginning, it was terrible. She just looked at the box and said 'no'."

9. Pedicure proposal

Bright idea - why not combine your proposal with a bit of pampering?

"My dad was giving his girlfriend a foot massage. He proceeded to do the whole 'This little piggy' toe thing. At the end of it, she found a ring on her toe. He was really excited to tell me this story immediately after it happened. (This is my dad's second wife, not my mum)," wrote treesthrowawayfun. (Post continues after gallery.)

10. Stolen thunder

It may be a time to celebrate love and commitment, but probably best to wait until after you've left the ceremony.

"A guy I knew proposed at his brother's wedding reception. Not quite the same, but I still thought it was a jerk move. She said yes, too, but recanted it a few days later. I will never, ever, for the life of me understand why people propose in public," wrote the_opinion.

11. It's all up in the air

"My wife and I were flying to Tenerife on our honeymoon, and the air hostess announced over the tannoy that a passenger was going to make a speech. The rough-looking bloke then started about how he'd loved his partner since he first met her at Argos - before proposing. She accepted and there was a big cheer - it was cringeful." - fiftyacorns


12. Closing time

"I used to work security in a club. One night at about four in the morning we were clearing everyone out, and anyone who was waiting for someone would have to do so at the front door. There was a guy waiting for his girlfriend to come out of the toilet. I told the dude to leave, he wouldn't, told him again, he wouldn't. This went on for a little while, before he produced some sh*tty £20 Elizabeth Duke ring and said he was about to propose," wrote privateequityderp.

"For his own good, I practically dragged him out of the club, and I am quite sure, probably saved his relationship. How many women want to be proposed to whilst still adjusting their buttpipe from dropping bombs in a club toilet?"

A proposal doesn't always equal romance. Image: The Proposal.


13. Public spectacle

Turns out the answer isn't always yes.

"I was in Minnesota, at the HHH Metrodome watching a Twins game with my dad. In between innings, they put a big 'Will You Marry Me' sign on the huge electronic board, and cut to a guy getting down on one knee. Everyone is applauding, oohing and aahing, then we all notice something. She is shaking her head," wrote temporarypatch.

"This guy got shot down, and everyone in the stadium could see it. I really hope someone was able to make sure he got home all right, because I am pretty sure he didn't stay sober after that."

14. Out of context

"I went to a Postsecret Live show at Rutgers a couple months ago and there is a part at the end where Frank Warren encourages people to come up and share their secrets... well, after a half hour of people crying about abuse and rape and the saddest shit you could imagine this guy actually proposes to his girlfriend. Weirdest sh*t I have ever witnessed... and she actually said yes," wrote brinagabriella.

Do you have any awkward wedding proposal stories?