“She Slaps Him So Hard My Face Hurt”: 30 Of The Worst Proposal Fails That Had Witnesses Cringing

So my late-twentysomething sister was semiserious with a (slightly younger) family friend for a couple of years. He did landscaping and she worked in the film industry. He lived in a cabin in the mountains and she lived in the city. He owned cats and she was kind of allergic. She loved to travel and he wanted to stay where he grew up. He wanted lots of kids and she wanted her career. She loved him and adored his family, but she wasn’t 'in love' with him. From the beginning, he was talking about marriage and kids and what their life would look like together. She kept telling him that she had been really hurt before and wasn’t sure what she wanted long term. He decided to stay with her. One Christmas season, he was seriously pushing what their wedding would be like (his mom organized weddings/parties as a second job) and how many kids they would have, and so forth.
My sister really had to sit him down and explain again that she didn't think she was ready for marriage and might never be, and asked to please not push her into something he knew from the start she might not want. Cut to the Christmas Eve party with both families (because we are all friends), and he busted out a ring and got on one knee in front of EVERYONE. She leaned over and whispered in his ear, and he got up and followed her outside. They spent the rest of the night talking on the back deck while everyone ate, drank, danced, and exchanged gifts without them. They broke up a month later. They are both MUCH happier now!

My ex-husband proposed to me in the shower after picking a fight about elbow macaroni.

I went into the shower to calm down and he followed me- slipped the ring on my finger and asked.

How he got the ring in the shower without me noticing was by hiding it under his fat roll. It was his mother's CZ engagement ring from her 2nd marriage-

...every day I wish I said "No."

My boyfriend and I had discussed marriage. He said "I don't think I ever want to marry you." He meant that he never wanted to get married again (he's divorced), but that gives you a sense of just how suave a wordsmith my prince charming is. So anyway we decided we weren't going to get married, but that we'd still like to have a baby.

The morning the little stick turned pink, he shot down on one knee and proposed. In the bathroom. Holding a positive pregnancy test covered in my urine. I said no, of course. Eventually I relented. Romantic, yes???

We've been married almost 8 years (the kids are 7 and 8 1/2). So far, so good.

I was on vacation with some family about five years ago. While on vacation, we ended up going to "Dolly Parton's Dixie Stampede," which is a dinner-and-show type establishment, and not particularly my cup of tea, but my family wanted to go and I didn't want to be 'that guy,' and I'm glad I went, for what I saw was well worth the price of the ticket.

Before the show started, the announcer listed of a bunch of happy birthdays and the like, and then says something along the lines of "And, now, a special announcement from blah-blah." This guy is on the screen, pre-recording, and asks his girlfriend to marry him, and then the screen shows the guy, kneeling down with a ring in the audience at the show, asking his girl. His girlfriend is visibly horrified, and just shakes her head. You could almost hear the guy's heartbreak.

It was on that day that I learned not to do things like that unless (A) you're absolutely sure she'll say yes, or (B) you ask her in advance and just want to make a good story.

My friend worked at a Coldstone Creamery and some guy came in during the day and said "I'm gonna come in later today and put 20 bucks in the tip jar. When I do, I want you guys to sing "Iron Man" by Black Sabbath, and then I'm gonna propose to my girlfriend." My friend and her co-workers found it strange, but agreed.

Later that night, the man reappears with the girlfriend at the Coldstone. Awkward eye contact between the man and the co-workers ensues while they wait in the long-ass line. He finally gets up to the front, and puts the 20 bucks in the tip jar. No one sings right away, so my friend goes for it solo. DUH DUH DUHDUHDUH DEDEDEDEDEDEDE DUH DUH DUH. He goes down on his knee, pulls out the ring, and says "Will you Marry me?" There is a long, silent pause as the workers and all the people at the Coldstone wait. She pulls him off to the side of the store and they have a quick word while everyone watches. They then go out to his car in the parking lot and sit there. For hours. My friend was still working for about 4 more hours that night and he was still sitting out there with her.

My friend assumes that she did not say yes. I concur.

**THIS HAPPENED TO SOMEONE I KNOW!!!** A friend of mine ran a marathon and her boyfriend proposed to her right at the finish line. No chance to take take a breath, hydrate, or rest. Not only that, but he brought other people to photograph and videotape the whole thing. So now my friend has all these lovely photos of her looking sweaty and gross on the day she was proposed to. She did say yes.

I unfortunately didn't witness it but my best friend just got engaged and when her SO proposed they were in a little french deli. She had just put a massive mouthful of pie in her face when she saw he had got down on one knee. She was so shocked she spat the pie out all over herself, all over him, all over everything. She just sort of nodded ... it was very like her to do something like that so it's all fine but still ... I don't think he was expecting pie in his face. 

I was once at a friends gig who plays pretty crazy distorted rock with a s**tload of synthesisers and stuff. It was really quite low key thing with only about 20-30 people there and this drunk guy gets up on stage halfway through my friends solo and grabs him to whisper something in his ear. My friend looks super confused but kind of nods and continues playing. Then after the song says, "Hey, so this guy here wants to say something" and lets the guy jump on the mic who then slurring every word asks his lady up on stage. She comes up (appearing no where near as drunk as he was) and as she's looking worried and confused he gets down on one knee and grabs her hand, mutters somewhat of a proposal to her. She lets go of his hand, he stands up, she slaps him across the face echoing through the tiny hall and he stands bewildered as she storms off the stage. My friend then helped him off the stage and says to the crowd "Ah.. so. Lets go!" and continues a raging set.

I watched a man propose to his girlfriend at the top of the Willis Tower (formerly the Sears Tower) in Chicago. He got out in one of the glass boxes that allow you to look straight down, got down on one knee, and proposed. She wouldn't go out on the glass. She got on the floor, scooted out over the glass on her a*s, and wept the entire time (not out of happiness). It was the most awkward thing I expect I will ever witness.

I didn't witness it; I was the one who turned down a public proposal. It was entirely unexpected, since I had met the guy six days before. We were at Bible camp the summer after senior year of high school, and he immediately gravitated to me. I was a shy, bookish girl without many friends and was pretty but not in a flashy way, which was the style at the time. So I was flattered. I thought we might end up dating. On the last day, in front of the larger group (a few hundred teens), he dropped to one knee and proposed. I thought it was a joke and pulled his hands to have him stand back up, but he was totally serious.
He had misled the camp leaders into believing that he and I were serious and this was a love match so that they would agree to the public proposal between two teenagers, but that was not the case. Once I realized he was serious, I walked away shell-shocked while he stood there crying. It turns out he was leaving for the Army the next month and wanted a wife before then.