The 17 Most Cringeworthy Examples Of Marriage Proposals Gone Wrong

Marriage proposal fails are like a train wreck, they're soooo bad, but you can't help but to watch.

The Most Awkward Dinner Ever

My friend H. owns a Japanese restaurant and is a very cordial host. One of our friends who moved overseas several years ago was back in town and we took the opportunity to meet up at H.’s for dinner and drinks. It was a busy night in the restaurant, with our table of about 20, a table of Japanese people next to us of about 8 people and the rest of the downstairs dining area full. All in about 45 people there. The drinks were flowing and true to H.’s style, he was popping from table to table to invite rounds and drink together with the guests and was noticeably tipsy. We were mostly minding our own business when H. shouted above the noise, clapping his hands to get everyone’s attention. “We have an announcement at this table,” he shouted, motioning to the table of 8 Japanese people next to us. “This gentleman wants to ask this beautiful lady a question!” So at this point the entire restaurant stops what they’re doing and looks over. The Japanese woman, in her late 20s looks like a deer caught in the headlights, looking for a hole to open up and swallow her. The man was a very quiet, traditional Japanese guy. He didn’t pick up on it and reached down and grabbed a jewelery box from a bag under the table. The woman went noticeably whiter and started shaking her head. H., oblivious to what was obvious to everyone else in the room, was trying to keep the momentum, shouting for all to hear “he’s going to propose to her now!!” The restaurant was quiet. The Japanese guy mumbled something to her, and she put her hands out to reject the box. H. didn’t notice and kept loudly encouraging the room to clap on and celebrate their special moment. Our table, realizing this was not going to turn out well, turned away from the train wreck. Someone grabbed H. and told him to ease off, which finally seemed to get through to him. He made another announcement, slightly embarrassed to the diners, “oh, what a shame!” It turns out that the guy was just giving her a necklace. H. has misread the entire situation and the poor woman had thought she was being proposed to. Embarrassed, she eventually accepted the necklace just to take the attention off them. You could see she was ready to deal with it later.
But it was not over. 10 minutes later, another round of shouting and clapping. H. yelled over the restaurant, “that was not the proposal before! He’s ready to propose now!” Everyone stopped and turned again to take in the scene. The woman was staring bullets at H. The guy reached down and grabbed another box from under the table. Somehow the subtleties of the previous 15 mins had not hit this guy. H. was making a big scene, excitedly pouring sake and whiskey and getting people to clap along with him. The guy proposed. She rejected. Room went silent. H. seemed not to notice and went on celebrating. Another 10 mins later and she had been coerced by her table into accepting the ring, which she wore on her hand and pushed a very angry smile through her teeth. Everyone else was cringing and feeling awful for her. (Source)

He Imperial Marched Away

I work in an airport in International Arrivals, so I see joyous reunions daily that are so filled with love that it makes me want to puke. (Can you tell I’ve been working there for a long time?) One day, I’m sitting in my store minding my own business, when all of a sudden I hear a trombone. I’ve seen people play guitar, ukulele, saxophone, and the one time a drum set; but I’ve never heard a trombone in international arrivals. So the song starts going, and I recognize the tune… It’s the Imperial March from Star Wars. I’m confused as f*ck, and trying to find out where the hell this is coming from, so I’m scanning the crowd when I see this girl who’s face is beet red. I’m assuming she has something to do with whatever the hell is happening, so I keep my eyes on her. She ends up walking to this guy who (surprise) is playing the trombone. He finishes up the song, passes his trombone to the person next to him (I’m assuming it was his friend), and then gets down on one knee. The girl is about 25 feet away from me, so if there were words exchanged, I did not hear it. But, what I did see was the guy smiling, then suddenly look dejected, stand up and walk away from the girl while she just stood there with her face still red like a tomato. That was super awkward to watch. (Source)

The Easter Egg Hunt Is Cancelled

Oh man I feel awkward just recounting this story. Wasn’t me – but I was dating my high school boyfriend and spent Easter with his family. His cousin (I’d say he was about 24) decided to stash a ring for his girlfriend in an Easter egg and send her on an Easter egg hunt. He spent all morning planning it out and putting people in charge of snapping pictures, popping champagne, etc. Girlfriend gets to the house and boyfriend tells her she has an Easter egg hunt to go on. She gets pissy, says she’s tired and doesn’t want to “do that sh*t”. He finally breaks down and says “there’s a really special thing in the egg that I know you’ll be excited to find.”… And she said “if it’s a f_cking engagement ring the answer is no.” But now he’s dating a Miss America contestant and I recently saw that ex girlfriend and she was working at a Claire’s, and she told me all about her boyfriend who sells phone cases at the stand in the mall. So I guess it all works out in the end. (Source)

I’m Going to Take That Proposal Back

I had someone propose to me then take it back an hour later. In one day, I had a boyfriend, a fiancé, an ex-fiancé, and an ex-boyfriend.
To elaborate: We went for a walk one day and he was visibly nervous. He finally stopped and said very hesitantly, “I’ve been thinking . . . of the long-term benefits of . . . marriage. Of a marriage-type thing.” Then he said he’d left the ring in the car but would pretend his wallet was the ring box. He got down on one knee and asked officially. I said yes. We walked home and he told me not to tell anyone yet. This was the first inkling I had of something being wrong (the aforementioned awkwardness and scatterbrained-ness were characteristic of him). We got back to our apartment and ate dinner as usual. He was quieter than normal. After, when we were sitting on the couch, he put his head between his knees and said, “I’ve made a huge mistake.” We ended the engagement (only a half hour) and broke up. I took a very long drive and came back three hours later. We talked and agreed to keep dating. Four months after that, he told me he wanted to break up for good. When I asked him why, he hemmed and hawed awhile before responding, “We went to Target way too much. Also, I didn’t love you.” We still haven’t talked. We dated for nearly four years before the “proposal” then he almost immediately vanished without a trace when we broke up. (Source)

No, I Can’t Help You With Your Citizenship

I worked on a cruise ship in the main dining room a number of years back, you tend to work in the same side stand with the same 5 people every night. One of those was a cute Filipino girl who I would constantly flirt with while working, we got along famously. After a month or so I was thinking how I would really like to start something a little less playful and a little more serious, and well it turns out she was thinking the same thing! She popped the question one night while we were cleaning up, “Hey , would you marry me?” I laughed and said “Of course I will,” thinking this is just us playing around still. Turns out it wasn’t. “I can pay you,” she said after I turned her down, “3,000 dollars,” which I also turned down. I’ve never had a relationship turn so awkward so fast, she barely spoke to me for the rest of my contract, I like to think it was because she was heartbroken, not because I wouldn’t help her get citizenship. But either way I feel terrible. And kind of amazing! Someone proposed to me! (Source)

These Damn Boots!

I am an emcee. I have told this before, but I have been asked to be part of many such things, but for some reason, very few go through with it. Like only 1 out of 10 people who plan to do it onstage actually show up at the event. Almost ALL that do, the girl says yes, with crying, applause, and kisses and hugs. One went really badly. It was at a cosplay contest, and I recall the guy got on one knee and proposed. The stunned girl said nothing, shook her head, and ran off. Then, the guy (in costume — a kind of “medieval rogue” or Robin Hood-ish affair) had to stand up from one knee. His boots were too tall for his legs (either that or he stepped on his cape), so he pitched to one side and fell over. Then he got up, and left. Audience was dead quiet. I didn’t know what to say, so I just went onto the next contestant, and pretended like it never happened. Later, at the afterparty, the judges and the staff were all gossiping how horribly awkward it all was. One of the judges admitted, “I almost fainted dead of embarrassment in sympathy…” (Source)

The Silence Was Deafening

I’ve seen a guy get turned down at Universal Studios City Walk. Everyone cheered and got happy and when she said no, the silence was f*cking deafening. He got up, brushed his knee off and they both walked away quickly (Source)

He Struck Out

Saw it happen at a ball game once, did the whole jumbotron thing with the text and then the closeup of the couple. The girl actually laughed and then you could see the guys dejected face. He started to lump back into his seat and looked like he was going to cry before the jumbotron cut off, and the place started to boo the f_ck out of the girl and throw sh*t at her. Security had to help her get out, kinda f_cked up they acted that way, no one knew their story. They could have been on their third date and he was a weirdo or something (Source)

This Can’t Be Real

I wasn’t denied but didn’t get a direct yes right away. She said “Wait… No. That’s not real.” I had to convince her I was actually proposing. We were in Ruby Tuesdays. Not my proudest moment, but it worked out. (Source)

Fateful Rejection

Overheard her on the phone saying she was worried I was going to propose and that it was time to end it. Ended it then and there. Already bought the ring…Took it back to the shop I bought it from and kind of broke down trying to explain why I had to return the ring. The girl at the counter demanded to take me out for drinks that night and we had a great time getting pissed whilst laughing at my whole situation. 3 days later, today, she (ring shop girl) left me a message asking if I want to take an impromptu trip away with her over New Years. Have been staring at the message all day now. (Source)

Public Pressure Made Her Say Yes

Flew to Wisconsin from Texas to surprise her for college graduation. Told her all along I couldn’t make it only to surprise her. Arranged a friend to get her there and came around the corner at the perfect time. I stupidly hired a photographer to shoot the moment and after which made it even worse. Got down on one knee and she said yes. We went out to dinner that night and that was where the truth came out. “I only said yes because all those people were there.” Seriously, don’t do it in public, that was the worst part. Foolishly stuck around for another 1.5 years and broke up. Shit messed me up hard and now I see a therapist regularly. (Source)

Don’t Mess With the Pickle Tradition

Her family did this thing where she hid a pickle ornament in her tree and her and her siblings would have a race to see who could find it first and the winner got an extra present. So I asked her mother her father and her siblings if I could use this as a way to propose and they thought it was the greatest idea. When they purposely let her find the ring she not only said no but insisted I leave. Haven’t talked to her since. 4 years and all my love wasn’t good enough I guess! (Source)

Arranged Marriages…in Canada?

In high school, I decided I wanted to learn how to play the piano. I found a local teacher and signed up for lessons. Since I was doing early-level lessons, most other students there were much much younger than me and I pretty much avoided them. There was one other older girl about my age but I rarely saw her and never spoke to her. At the end of my first year, there was a cheesy year-end recital. I embarrassingly played “The Entertainer” with a bunch of little kids. Anyways this girl played her song, and afterwards we were talking. Her mom came over and started talking to me and my mom and randomly asked if we would like to arrange a marriage. I thought she was joking and laughed, but I was wrong. I don’t think it was a cultural thing either, they were two english-speaking Canadians like us. She kept asking, and we were just kinda in shock and had to say no. I could tell the girl was humiliated and avoiding eye contact. My mom loved it though, and kept joking that I should “go for it”. (Source)

Close Call

My Mom and dad were in a car crash. When my mom went in for x-rays they did a test first and found out she was pregnant with me. When my dad found out he proposed to her on the spot neck brace and all. She said no, explaining that she didn’t want to get married just because she was pregnant. My dad started to cry explaining that he had plans to propose on Valentines day and already had a ring. A week later she accepted and they’ve been married for 22 years. (Source)

24 Hours Too Late

I was preemptively turned down, 24 hours after I picked the ring up, and 24 hours before the planned proposal. She said she was having doubts and was considering moving to the other side of the country, which she did three months later. She was married to some other dude inside 18 months. The real kick in the balls on this was that I’d already had the ring sized (because, make no mistake, we talked about it A LOT before I went ahead and bought the thing) so I couldn’t return it. I still have the goddamn thing a year and a half later. I swear if I had the vacation time I’d get together nine friends and go chuck it into a volcano. (Source)

He Wasn’t Her Soul Mate

I took my fiancé out to an island in Boston harbor to propose with a view of the entire city spread before us. She said yes and we had a beautiful day and returned to our warm, bright, shared apartment. My head began to fill with dreams of a shared house, children, a future. 3 months later, she told me she had fallen in love with her soul mate – a married man she met at her internship. For 3 months I tried to make her see my love for her, waking up early every morning to make her breakfast, date nights every weekend, and in the end she still chose him. It’s probably better this way. I’m moving out of our apartment over this break, while she’s home with family. It’s times like this that you realize how important family and true friends are. Merry Christmas to everyone who feels alone and rejected out there – there are people who love you too. (Source)

Not the Response He Expected

I had been with the lady in question for two years, we were in our own little world doing our own thing together. We had ups and downs but nothing too dramatic, and I at least was happy. I saved for a while to buy the ring and had a day planned out culminating in The Question. I did the one kneed bit and she flat out laughed, but said yes. I was overjoyed, euphoric so put the laugh down to nerves or shock perhaps, who cares, I was getting married! The next day I got up first, took the dog out and got home to find her putting down the phone. I asked who she had told about our engagement as we had agreed to tell people together. She said she had to talk to someone and dismissed it. I joked that it was her lover and she was having an affair. Her face dropped, my heart sank to my ankles and she then told me, quite plainly and calmly that yes, I had guessed right and that she was off to pack a bag. And then she did, three days later it was almost like she was never there. F*cking b_tch tore my soul out and wiped her arse with it. I would love to wrap up with some kind of revenge or twist to it but she married him. Hurt a more than a bit, caused some depression and a bit of drinking. It seemed totally out of the blue at the time but I always was a poor judge of character when it comes to women. (Source)