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

My high school sweetheart and I had been living together for several months when he caught the flu. It was the first time I'd ever seen him really sick and I was determined to take care of him but after a few days was getting worse. I tried to convince him to go to the doctor but since we didn't have health insurance he insisted he'd be fine and I gave in. I try to make him comfortable on the couch since its closer to the bathroom and he cant keep anything down. Around midnight he's getting delirious. He's had a fever for days, dehydrated from throwing up all week and he's spouting gibberish. He barfs all over the couch and can't stand up. I tell him I'm putting my foot down and he's going to the doctor first thing in the morning. He suddenly gets quiet and looks at me very seriously and says,'You're so good. You should marry me. You want to marry me?' and then passes out. I was shocked but didn't take him seriously obviously and just focused on bringing him around so I could get him off the couch and into bed. When morning rolls around his fever has broken and though he's weak and pale, he's doing much better. He asks how he got into bed because he can't remember anything from the night before and I entertain him with the story of how I dragged him to bed after he proposed and passed out. I think the whole thing is funny but he doesn't laugh so I look up and he says 'Well, what was your answer?' We just celebrated our 13th wedding anniversary. TL;DR - Vomit can be romantic under the right conditions. 

I used to work the jewelry counter at Target. Two kids, probably 13 or 14 decide that it's time to get officially engaged. They purchase a cheap cubic zirconia ring, 10k gold overlay, $9.99. The boy proudly pays in ones and a handful of change. He gets down on one knee, says he loves her forever and puts the ring on the girl. She giggles "Daddy's gonna KILL me!", then they run giggling into the night. I like to imagine they lived happily ever after.

I saw one of those once at a baseball game. I was sitting I think about 2 rows behind them and the guy gets down on one knee and says his spiel....the girl gets up and throws beer in his face screaming "YOU DUMB F**K, I KNOW YOU SLEPT WITH ANNA LAST WEEK!" I haven't laughed that hard since.

I proposed to my husband in the worst way, IMO.

Let me preface by saying, that I had been married before and I really, really believed that marriage is overrated, I had already warned him many times that I would never get married again.

So, we'd been in a long distance relationship for about 6 years, sometimes on/off, but mostly on. At the time, we were kind of "off" but still together. One night he calls me, I'm sitting a bar, not drunk (yet) and tells me over the cell phone that he's being deployed to Afghanistan. I immediately burst into tears because now I realize how much I really do love him and I'm very scared. So, I propose to him. He accepts. He goes to Afghanistan.

He comes back home, we continue on as normal. No wedding plans are made because I'm busy with my business, not sure when I can leave the states to move to Canada, etc, so it's just on the "back burner".

I'm going to go to Canada for Xmas, first time for me to visit his family for Xmas last year (2011). When, 2 weeks before I leave for Canada, he shows up at my house in Phoenix from Canada and when I open the door, he gets down to his knee and proposes to me "officially" and THEN hands me the invitation to our wedding, he had planned the whole entire wedding and all I had to do was show up! So, he was there to take me shopping for a dress! Some woman may not like this, but I LOVED it. I ADORED it and it was an awesome wedding.

That was in December, but couldn't move to Canada to be with him until April, and then we had to wait until June to take a 2 month honeymoon to Hawaii that just ended last night. Love this man.

tl;dr I (female) screw up proposal, he (male) comes back 3 years later and does it even better than the "right" way.

I proposed to my wife in Times Square at New Year's Eve (I was going for maximum cheezy!) She was pretty emotional and took a while to believe I was serious (even though I had a ring). This being New York, strangers started shouting at her to "HURRY UP LADY, WHAT'S IT GONNA BE? WE DON'T HAVE ALL NIGHT"

Pilot here. Guy ask me to fly him and his SO over a field, where 150 people had formed a heart and two rings. Huge show, I was really impressed. When she saw it, her response was: "Look at all those idiots! How ridiculous is that??"

He did not ask his question that day.

Well I suppose my own was pretty terrible by society's standards, but I think conventional romance is b******t. Anyways... I was sitting on the couch in our apartment, surfing the web on my laptop and my (now) husband was next to me playing L4D (I think that was the game he was playing). It was summer and we were both planning on starting college in a new city together at the beginning of the next year. I was on our future college's website reading all the forms and c**p I needed to get done when I looked at my now-husband and said rather nonchalantly, "We should get married." and he replied just as casually, "Yes, we should." I said, "How about September or October?" and he was all "Works for me!" We had a very plain wedding that October and Have been very happily married for almost 3 years since then! 

Saw a couple in a jewelry store when my wife and I were looking. Guy asks to see a ring, kneels, "will you marry me?".

She flips....ohmygod!ohmygod!ohmygod!ohmygod! yes yes yes!!

He says "great!" then hands the ring back to the employee and tries to leave the store. He proposed with a borrowed ring. Tries to explain to the girl he couldn't afford the ring but wanted to propose correctly. She slaps him so hard my face hurt (she put her whole body into the slap) and starts screaming about how her mother was right, etc. etc.

No clue if they ever got together, but it was hard to watch.

During college (and for several years afterward), I rowed gondolas for extra cash on the side. I had seen about 500 proposals during that time. The only 'no' I've ever had came from a guy who pulled out all the stops. Dinner, Venetian gondola, roses...even a customized message in a bottle to be 'found' during the Venetian gondola ride. So when the time came, he knelt down and popped the question. After what felt like a full minute of stunned silence, she took that moment to inform him that she was already married.

I proposed to my wife in Dublin, which is more difficult than it sounds because it's not a romantic city. After dinner, I decided that the Halfpenny Bridge was about the best place to get the job done. Right in the middle of my proposal, I hear the unmistakable sound of a drunk guy p***ing off the bridge not 10 feet behind me. Ireland has never let me down.

I had been dating this girl for about a month or two while we were in college, and we lived close enough in the summer to see each other frequently, so I was over her house and we were getting stuff ready to grill out when a car pulled up. We assumed it was some of her friends, who we had invited, just arriving a little bit early. She peeked out the window and gasped. "Oh s**t, it's Matt!" Matt was an ex-boyfriend from high school. They broke up senior year, but he had been pursuing her since then despite constant outright rejections. "Do you want me to take care of this?" I asked. "No, I'll deal with it. He'll just try to start a fight with you." So I sat by the window and watched the whole thing. It was short. He said that he wanted to talk. She said she really didn't want to talk, she was having people over, and besides, they had talked everything out a while ago and everything was settled. There was nothing more to talk about. He was a bad boyfriend, it was three years ago, she moved on, he needed to do so as well. That's when he doubled down. "I know the reason we've been apart. We were in high school. We were kids. We weren't adults. So you can't ever see me as an adult. Not until I man up. You need to know that I'm serious about this. That's why I have this!" He got down on one knee and pulled a ring box out his shirt pocket, just like a jewelry commercial. He opened the box and said, "Beth, will you marry me?" She tried really hard not to burst out laughing, but only halfway succeeded. "OH MY GOD, NO! GO AWAY! There are people coming over, Matty, don't embarrass yourself any more than you already have. Seriously, just go!" He had this quizzical look on his face, like shock and disbelief. He really thought this was the right play. After a few seconds, he got up, put the box back in his pocket, and walked back to his car without saying another word. She came back inside. "I can't BELIEVE that just happened," she said in a mixture of amusement and anger. I was mostly on the side of amusement, so I asked if the ring was nice. "It wasn't even a ring! It was a tiny note that said 'Any ring you want.'"

I was at Taco Bell with a few friends of mine, including a guy and a girl that had been dating for a few weeks. A few of us got tacos, but the girl only got a diet coke.

So her boyfriend asks her, "Do you want hot sauce?"

She says, "uh... No. I just got a Diet Coke, what the hell would I want hot sauce for?"

He says, "I dunno. But I just think it would be really good if you had some hot sauce."

They argue about whether or not she needs hot sauce for awhile, until finally she just says "ok, whatever."

He goes over and gets some. Comes back with a packet, gets on one knee, hands her the package that says "Will You Marry Me?" on it, and pulls out a cheap looking engagement ring out of his pocket.

Keep in mind they've been dating about 3 weeks at this point, and we're in the middle of Taco Bell.

She gets this look of absolute shock on her face. And then says yes. They got married a few months later. They got divorced a few months later. And that was the most humiliating trip to Taco Bell of my life.

TL;DR - guy proposes to girl In taco bell with a hot sauce package and she says yes.

I wasn't there for it, but saw the video.

I work for a place that caters all sorts of events. We did this ridiculous rehearsal dinner for a wedding. I say "ridiculous" because I've never heard of a rehearsal dinner needing an auditorium and several other spaces for guests. The parents of the bride were loaded and just awful (Common, accepted practice is that after all the guests have eaten, staff get to have a little plate. The bride's father chewed us and our boss out for it even though he was just going to have us pitch the leftovers at the end of the night.)

Anyways, prior to the guests arriving the family of the bride handed me a DVD to play over the projection system. This DVD contained the couple'd engagement photos and music but it also contained video of the proposal. It was the most awkward thing I've ever seen.

The dude walks into the house as her father opens the door. The guy looks so nervous, but not nervous like he's going to propose, nervous like he doesn't know what to do on camera. "Do I stand here? Where's my mark?" The camera pans over and his fiancé is standing at the top of a massive staircase (these people are obviously loaded) in probably her most elegant dress. It takes her almost two minutes to descend the staircase. I know, because I timed it since it was on a constant loop all night. The guy awkwardly shuffles over to her and gets down on one knee and then ADJUSTS his position for the camera. The ring is placed on her hand and then they just sort of stand there. The video then starts looping again.

It was the single least romantic thing I've ever seen.

I proposed a couple years ago, don't think it was terrible, just different. I had taken her out to dinner and while waiting for our food i asked to see her promise ring, started playing with it and pretended it it got stuck on my pinkie, she starts to worry we will have to get it cut off when i said, "or we could just replace it" hands her new ring, "With this.. Will you?"
She said yes :)

I sure did. This happened three years ago. Some friends and I decided to road trip down to Orlando and go to the amusement parks like a couple of 21 year old children. Well we were in one of the Disney parks (magic kingdom perhaps?) and I saw one of craziest rednecky things ever. So we're looking at a map figuring out the plan of action and all of a sudden we hear "Boy, what the hell do you think you're doing?" Some guy, like 5 feet away, was on his knee with a ring out in front of a girl, and an older guy was next to him yelling. This is where it gets weird. The guy said "thats your damn cousin you f****n idiot, get off your goddamn knees before I beat the p**s out of you". This obviously got our attention. The guy doing the proposal (who I will call George Michael from now on) started crying and said "but I love her and I want her to be my wife and you and no one else can stop this from happening. Mary, will you be my wife?" The girl (Mary I guess) looked at him and said "why are you doing this? don't you ever talk to me again! I hate you for this!" And she ran off. Then George Michael ran in the other direction. The older dude was pissed off beyond belief and the rest of the family. I wanted to clap but I felt like I would've been killed.

So I had gone to a Dallas Mavericks game in March with my dad, and during halftime, they had this couple come down and play a game. The girl was very clearly not into basketball at all, and her partner very clearly was. In the game, the cheerleaders held chests with letters in them (they were supposed to be prizes). Eventually she opened all of them, and it spelled 'Mavs' and 'Will you marry me.' When they closed the chests, she turned around, he was on his knee…and she just kinda stared at him, not smiling, and picked him up off the ground and whispered in his ear. They left with her walking in front trying to keep it together while he nodded uncomfortably…most awkward experience ever.

I proposed on a dinner cruise and told her I was gonna throw her overboard if she said no. The couple next to us interrupted to ask if she needed help.

I was in Paris for business and decided to walk by the Eiffel Tower. As I was walking, I noticed a girl was holding a lot of balloons, so many that I was surprised she didn’t up and fly away. In front of her, a guy was kneeling down on one knee, holding one of her hands. He was saying how much he loved her and wanted to spend the rest of his life with her. She looked completely shocked and surprisingly uncomfortable. As he finished with, ‘Will you marry me?’ she shook her head no, apologized, and walked away, still carrying the balloons.
The guy stood up, took out a cigarette, lit up, and then proceeded to sit down at a nearby café looking as if he didn't have a care in the world. He ordered an espresso and read a newspaper as if nothing ever happened. It was the strangest thing.

Well this might be a common one with a bit of a spin.

I was with a few friends at Burger King at around 3 in the morning (yes Burger King of all places) and the only other people who were eating was a middle-aged couple. The woman got up to go to the bathroom and the husband slipped something out of a ring-box into the woman's burger. When she came back she ate the burger without noticing anything. The man went wide-eyed and told her she just swallowed the ring, and then asked her to marry him. She said yes, and my friends and I burst out laughing.

I knew a guy who was at McDonalds with his girlfriend one time, and as a joke he wrapped a fry around her finger and said, "Will you McMarry me?"

She started crying and called her mom and like started planning the wedding the next day. He hadn't meant to propose but he didn't have the heart to tell her so, so he just married her.

Lost touch since then, but I would be very surprised if they're still married today.