15 Cringe-Worthy Marriage Proposals Gone Wrong

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2 days ago

Before anyone walks down the aisle, there's one big moment that sets everything in motion: the proposal. However, sometimes popping the question misses the mark just a bit. So here are some of the most awkward, painful, and just plain wild proposal rejection stories we found on Reddit:
"My story is pretty brutal. I was walking down the beach with my then-girlfriend, and an airplane flew by with a banner that said, 'Tiffany, will you marry me? —Tom.' My name is Tom, and her name is Tiffany, but that was not my proposal. She starts screaming 'yes' and hugs me. I am in shock, staring at the sky, not even realizing she has her arms around me. After I was silent for a while, she figured it out. It was the quietest, longest, most painful walk home of my life. What a fucked up coincidence."
"I was in 3rd grade when some dude came into the classroom and proposed to our teacher. She just started crying and left the classroom. We found out that her answer was no."
"Oh man I feel awkward just recounting this story. It 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. The girlfriend gets to the house, and the boyfriend tells her she has an Easter egg hunt to go on. She gets pissy, says she's tired, and doesn't want to. He finally breaks down and says, 'There's a really special thing in the egg that I know you'll be excited to find.' She said, 'If it's a fucking engagement ring, the answer is no.'"
"My good friend was dating this guy for nearly two years. I could tell things were getting a bit stale with them, and one day when we went out to get lunch she told me that she was going to break it off with him. She seemed far more stressed about hurting the guy and was asking for advice. Right in the middle of me giving her some input, the guy comes in and looks a bit frantic. He musters up the courage and walks right to our table, completely ignoring me, gets on one knee and pulls out the ring. I was so in awe of it being the worst timing ever, that my mouth was open in shock. Guests gathered around the table started cheering, but my friend just got up and walked out to her car and drove off. I almost died from second-hand embarrassment. All I remember is the gasps and snickering and he just sat in her place looking crushed. I didn't know what to say. I got the check and gave him a pat on the back. My friend is still recovering from the whole ordeal..."
"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. I did the one kneed bit, and she flat-out laughed but said yes. I was overjoyed and euphoric, so I 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 just getting off the phone with someone. I asked if she was telling someone about our engagement but she didn't answer me. 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."
"I saw it happen at a ball game once — the whole jumbotron thing with the text and then the closeup of the couple. The girl actually laughed, and then you could see the guy's dejected face. He started to lump back into his seat and looked like he was going to cry before the jumbotron cut off. The place started to boo the girl, and people started throwing shit at her. Security had to help her get out."
"I got turned down for buying the 'wrong ring.'"
"I work in an airport in international arrivals, so I see joyous reunions that are so filled with love it makes me want to puke. (Can you tell I've been working there for a long time?) One day, I was sitting in my store, minding my own business, when I heard a trombone. The song started going, and I recognized the tune... The Imperial March from Star Wars. I was confused and trying to find out where it was coming from. As I scanned the crowd, I saw this girl whose face was beet red. I'm assuming she had something to do with whatever is happening, so I kept my eyes on her. She ends up walking to the guy who is playing the trombone. He finishes up the song and gets down on one knee. The girl is about 25 feet away from me, so if words were exchanged, I did not hear them. But, what I did see was the guy smiling, then suddenly looking dejected. He stood up and walked away from the girl while she stood there — her face still red like a tomato. It was hard to watch."
"I had been dating my girlfriend for seven years and she always said that I could propose to her with a ring pop and the ring didn't matter. After her cousins wedding, I got down on one knee and proposed to her with a plastic Green Lantern power ring. It was the pink Love ring. She said no. Apparently, the gesture was not enough."
"I used to work at a fine-dining restaurant and saw a few proposal rejections. The incident that stands out the most is when a guy did the whole having the ring brought out with the dessert and proposed. The woman seems shocked and pretty annoyed at the situation. She turned him down. One of the servers overheard her say, 'You're not even my fourth or fifth choice.'"
"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.' 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 and broke up."
"We were in a long distance relationship but we lived together before she moved, so we had been together for awhile. I flew out to see her and propose, but as soon as I landed I got severely sick. My mother took it upon herself to ask my girlfriend for me. She immediately told her no, but I was never informed of this. I went to propose and heard it all laid out in front of me."
"I come from a traditional Indian home. My parents thought sending me to a marriage convention would be a good idea, so I decided to go so I wouldn't have to deal with unnecessary drama. When I got there, I went to the first girl I saw and asked her to marry me. She said, 'no.'"
"I proposed on the Eiffel Tower. Had it planned out and all, but was really nervous and didn't know how to start. Then I saw someone had carved a proposal into the handrail. I read it aloud, and then asked my girlfriend if she'd marry me. My tone maybe was off, because she said, 'Of course I'll marry you,' like it was hypothetical (like yeah, I'd marry you, if you'd ask). That ended the conversation, we went on with the vacation a bit awkwardly, and then talked about it a few nights later. I said yeah, that was supposed to be for real..."
And lastly: "I never got the chance to actually propose because she basically found out I was planning on it and broke up with me. We are still friends, she just wanted to get her professional life sorted before her personal life, which is a reasonable thing to do honestly. No hard feelings, just sad that it happened. As I said, we are still very close, and things might work out in the future, or they might not."
Have you ever witnessed a cringey marriage proposal rejection? Let us know via the Anonymous Comments form below and you could be featured in a follow-up post!
NOTE: Some submissions have been editing for length and/or clarity.