February 21, 2023 | Eul Basa

Brutal Failed Proposals


Preparing to propose is nerve-wracking.  Then, when the big day comes, one musters up all their courage to pop the question in hopes of hearing a “YES”.  However, the universe, being what it is, sometimes has other plans. These Redditors share their stories of marriage proposals that totally failed. Keep reading to see what happened when the “I Do’s” turned into an emphatic “I Don’t”!


1. She Flew Off The Handle

Many years ago, my dad, Steve, was at the beach with his girlfriend of about two months, Julie. One of those planes with a banner out the back flew past, with the message “Julie, will you marry me?—Steve”. Julie apparently freaked out and ran off while my dad was trying to explain that it wasn't his doing; he had no idea.

He thought it was his friend's idea of a joke when he walked down the beach and met a very happy couple named Julie and Steve. He got rejected for a proposal he didn't make.

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2. Jumping Off The Deep End

My mom is a horse carriage driver and has a lot of people propose while on rides. One night, a couple was taking the company's most romantic ride. The guy turns to the girl mid-ride and asks her to marry him. It went hilariously wrong: She screams, "I already told you no before", then jumps out of the moving carriage and runs away down the road.

Yeah, my mom tells THAT story a lot.

Failed ProposalsFlickr, Wally Gobetz

3. A Don’t At The I Do’s

At the wedding party of another couple’s wedding, a guy got down on one knee. The vibes got so bad so quickly. Everybody sitting at his table—along with his then-girlfriend—had a complete and utter look of “don't do it” on their faces when he proposed. She got up and walked away, face as red as a tomato. The guy chases after her, screaming at the top of his lungs, "Don’t we love each other? I got you a ring, babe”.

He then said the heck with it, called her a name and came back to the table. It was the most awkward wedding party of my life.

Failed ProposalsShutterstock

4.  Easy Return

I bought a ring back in 2003. I was in the Army, and she lived back home. I only got to see her on three-day weekends, four-day weekends, passes, and leave. That being said, we still had an average of about two months out of the year that we got to spend together. The ring was awesome—platinum with a solitaire. I drove up to surprise her, and before I even had the chance to propose, she said we have to talk.

She dumped me, and all I could think to say was, "That's OK because the jeweler will take the ring back". Then I went to a high school friend's house and partied. I displayed the ring prominently on top of my computer. When I got back to my base, I went to the jeweler and returned it. Then I took the cash and bought a new computer. In retrospect, that computer brought me more happiness than she did.

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5. Michelle, Michelle

At my aunt's 50th birthday party, which also happened to be New Year’s Eve, there were about 100 people there. She managed a hotel, so they were using one of the banquet rooms, and the party was in full swing. Out of nowhere, this trashed guy goes up to the DJ and orders him to turn off the music because he has an announcement.

The DJ seems confused, but no one else comes to his rescue, so he turns the music off and passes this guy the mic. That was a big mistake. Most of the crowd seems pretty confused, as the guy was unknown to most of us. However, my female cousin, Michelle, starts to walk up towards the stage, pleading for him to come down. He has something that he needs to get off his chest, though.

Soon he's in the middle of a teary-eyed rant about how he's always loved Michelle, how he'd do anything for her, and after all that they've been through together, he just really wants to take the next step and make it official by publicly declaring his undying love. The next thing you know, he's on one knee, and he has a ring out and everything.

Michelle was in tears now, and she was just shaking her head back and forth, still pleading for him to come down off the stage. He refuses to come down until she gives him an answer. After an incredibly uncomfortable 30 seconds or so, the impasse comes to an end, with Michelle fleeing the banquet hall with one of her girlfriends.

The guy seems genuinely shocked and trips on his way down the stairs as he tries to follow her. But it gets worse. He completely wipes out, skidding across the dancefloor on his chest, the half-empty drink in his hand flying out in front of him. Next thing you know, he's being shown off the premises. Apparently, he and Michelle had never even dated. He was a casual acquaintance and a co-worker at the pub where Michelle worked. It was all completely surreal.

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6. Taco Time Turndown

We had literally been dating for a month and I was preparing myself to break up with him; the reason being he only would talk to me in a "baby voice" which means how people talk to infants. Imagine someone refusing to stop talking to you like you were six months old—it was infuriating. So we met at a Taco Bell and I laid down the breakup. He then got on his knee and proposed while he was crying.

My immediate response was to ask how long he had the ring—three weeks. I said no and he got up and continued to cry. Then he asked for a hug and I agreed, but I don’t know why. He shoved his taco-stank lips on mine and gave me a nasty kiss. I jerked back and as I wiped my mouth, he was already walking out the door. To this day, I still get flashbacks of the disgusting taco kiss. It was more disturbing than the proposal.

Failed ProposalsShutterstock

7.  More Than Just A Price Got Dropped

I was at Walmart at two in the morning. I was in college, and 2 AM always seemed to be the best time to go. There was hardly anyone there. No lines, the shelves are being restocked, and all the crazies come out. I was just finishing my shopping and heading to the checkout counter when I heard an employee get on the loudspeaker.

He sounded amused and a bit confused as he said, "This is a message for”, and gave a woman’s name. He then gave a man’s name and said the guy wanted to ask if he could take her hand in marriage". As I'm checking out, I see a woman in tears running to the customer service section. I can vaguely hear the man shouting, "So is that a yes, Baby"?

Chaos broke loose. There was so much screaming and yelling. As the lady finished checking me out, I saw a few employees run to the service center. The shouts got louder and I heard crashing like someone was just throwing whatever they could get their hands on. I paid and left quickly. When I got all my bags into the car and sat down, I saw a security guard, three employees, a man, and a woman. The man had a bloody nose.

Failed ProposalsShutterstock

8. Carnival Crusher

A friend of mine once said “yes” to her boyfriend, who had proposed to her at a carnival in front of a lot of people. When they got into the car to drive home, she told him she didn't really want to marry him. She had just wanted to spare him the embarrassment of getting turned down in front of all those people. He stopped the car and made her get out. She walked home alone and they never spoke again.

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9. A Drawn Out Ending

A friend of mine proposed, and she said, “Yes”. A week later, she moved out,  but she "still wanted to be with him". A few months after that, she moved to another city, "for a job", but never mysteriously started said job. A few weeks after her move, she broke off the engagement over the phone, saying she just wasn't ready.

They had been dating, living together, and had pets together for eight and a half years. It wasn’t an immediate “No” but rather a bit more drawn out. It was still rough. The girl then moved even further away and started dating someone almost immediately, and was set to get married.

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10. He Was Entitled To Someone Better

My best friend went to Kettering (former GMI) and in his fourth semester started dating a girl from his class. She seemed good for him from what he said, but I was not very fond of her. She was a very spoiled rich girl type that constantly belittled everyone. My best friend came from a blue-collar family—both parents in factory work—and lived in a rough neighborhood.

After they were together for nine months, he told me, "I want to propose". Being the negative Nancy I am, I suggested waiting, as they were only together for a short time. He ignored me, bought a ring, and planned to ask her to marry him the next year. He picked out the 4th of July weekend, as he was going to her house for her parent’s large party. He should have listened.

Her parents threw a large party at their place on the lake and he worked up the courage to propose in front of 500+ guests at this party. He taps his glass, gets on one knee, and asks her. She let out a long deep laugh, looked at him, and said, "Yeah right. You're great, but I'd never waste my life with you". The parents were laughing so hard they were in tears, and most of the other guests were chuckling as well.

He decided to leave early and she stopped him. She told him, "It's not that I don't love you, but you're not good enough for me. We can date, but that's all I think I want from you". My friend gave her a long speech full of "take a hike you entitled brat" stuff, then left humiliated, but oddly liberated. She constantly tried to get back together with him and stalked him on Facebook for quite a while. The last I heard, she was upset that she was still single and that he was engaged to another girl. She had the nerve to write him a letter asking to be invited to his wedding.

Failed ProposalsFreepik, yanalya

11. Preschool Heartache

My 4-year-old son said a girl at his daycare was his girlfriend and he wanted to ask her to marry him on Valentine’s Day. So, I got him a little toy puppy and candies because I had to support my little man! When I picked him up, he came back with the toy and the candy and I asked what happened. He said, "She doesn't go here anymore". I talked to the daycare, and apparently, the girl was in foster care. Due to something in her case, she had been removed from the daycare a few days before.

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12. Au Revoir!

I was in Europe for a month last year with my girlfriend and we stopped in Paris toward the end of our trip, which was amazing up to that point. One night, we're on the second-highest platform of the Eiffel tower, and we see not one but two proposals happen right in front of us. Both said yes. So when we were both gazing out at the Paris skyline I got close and asked her, "What would you do if I proposed right now"? She replied, less than half-jokingly, "I'd jump".

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13. A Proposal Is No Joke!

I had been dating this guy for three months at university. Things were going really well. I, however, had just gotten out of a long-term relationship a few months prior and wasn't really thinking about the future. Not to mention, we had not been dating very long. After class one night, we were walking through the streets of Detroit.

We found this beautiful little place with all these trees. The conversation was great, the night was beautiful, it was perfect. He asked me to sit under a tree, which sounded good to me, as I was tired. He stammered out something about loving me. I told him I loved him too, and then he said, "Will you marry me"? I laughed at him.

I thought he was kidding. He shrugged it off and the incident was forgotten about. Three years later when he tried it again, I found out he was serious that evening. We've been together for seven years and married for four. I still feel horrible, though.

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14. Oh, Brother!

Last year I had the pleasure of attending my cousin’s wedding. The reception was long and fun filled with many different types of assorted drinks, since my cousin had a thing for exotic booze. After a few hours and many empty bottles, many guests were extremely hammered—something that seemed to be foreshadowed from the beginning. But the worst-case scenario happened.

One of the extremely sloshed men took a microphone from the DJ stage and began to express his love for the new bride. He spent a few minutes attempting to convince her to leave her new husband to be with him instead, throwing in a few insults to the groom, until a few men "persuaded" him to leave. This man ended up being my other cousin, the groom’s brother.

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15.  One Last Ditch Attempt

I said no to my ex-boyfriend. It was private, so it wasn't totally embarrassing for the guy, but it was still uncomfortable. We were actually in the midst of a breakup. One that I initiated because he was manipulative and just dumb. We were driving somewhere and he had given me his grandmother’s antique wedding ring. He said we should get married.

I asked him how marriage was going to make the relationship work when it was already failing. He stated definitively that marriage will solve all our problems! That we'll be happy! I laughed and then I cried. It was just his way of trying to keep me from leaving.

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16. The Second Time Around

My high school history teacher was in France with his then-girlfriend, on vacation. She apparently loved the famous painting of the water lilies by Monet. So, he found this little place near a French castle with a lake covered in water lilies. They sat on a little bench and he gave her a long letter describing how he felt about her, and why he loved her so much.

Then, when she looked up from the letter, he was already down on one knee with the ring, asking her to marry him. Our class thought it was just the cutest proposal story ever. And then she said no. Not because she was evil or anything, but because they both still had a few years of university left. She didn't want to get married before finishing school and also didn't want to be engaged that long. When he proposed a few years later at Niagara Falls, she said yes.

Failed ProposalsFlickr, Artem Beliaikin

17. My Best Friend’s Girl

When I was sloshed, I once tried to convince my friend's girlfriend to marry me. When she said, "No", I even got down on one knee and asked again. Before she could even answer, I tipped over and passed out. I did not believe that this really happened until one of my other friends showed me the video. The girl is still with her boyfriend, and all three of us are still friends.

Failed ProposalsShutterstock

18. He Didn’t Listen!

A guy friend of mine was dating this girl who told him that she did not like public proposals and she would say "no" to one on principle. He did it anyway, in a fancy restaurant, and got the waiters and half the other patrons involved. She smiled nicely, leaned in, and whispered, "I told you I'd say no to any public proposal, so you already know the answer. But if you want, you can act like I just said yes and I will play along until we leave".

I thought it was very classy of her to be willing to help him save face like that. When he recounted the story, I did the best I could to follow her classy example and refrain from smacking him upside the head like I wanted to do.

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19. Smooth-Talking Six-Year-Old

When I was in first grade, the girl who sat behind me had the same last name as me. Being the non-confrontational gentleman that I am, I figured I'd ask her to marry me because she wouldn't have to change her last name. It was the smoothest moment of my life as I leaned back in my chair, balancing it on the two back legs.

My head popped in from behind her right-hand side and just flat-out asked her to marry me. She of course said, "No" and my 6-year-old heart was broken—for about a second. I then flopped the chair back forward and continued on with my phonics book.

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20. Bi-Coastal Brush-Off

I broke up with my high school sweetheart during my senior year of high school. I felt like our lives were going in different directions, etc. Four years later, he contacted me out of the blue, and we started talking pretty regularly, just friendly. He lived on the East Coast now, and I lived on the West Coast. After a few weeks of texting fairly regularly, he invited me to come out to his graduation.

I said, “I'll think about it”. The next day, my mom calls and tells me he had called her to ask for help picking out an engagement ring for me. I called him, and he said, "I think we should get back together". I replied, "I think we should stop talking to each other". So, he didn't actually get around to proposing, because I cut him off at the gate. Yes, my ex-boyfriend was going to propose to me at his graduation, and we weren't even dating. We actually had not seen each other since the break up four years prior.

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21. Third Time’s The Charm

A woman I know had been dating this man for two years very seriously. She was in love and wanted to get married, and had been waiting for a proposal. It wasn’t happening, and she, being the assertive woman she was, decided to take matters into her own hands and bought a ring to propose to him with. She made reservations at a nice restaurant and arranged to have a corner seat where she could snuggle up next to her boyfriend.

About 45 minutes into the date, she grabs him around one arm, kisses him on the forehead, tells him she loves him and wants to be with him forever, and then pulls out a ring. His reaction was...not ideal. He subsequently became nervously sick to his stomach and ran to the bathroom to puke and didn’t return. She was distraught, but when she got home, she called him.

He answered and apologized for his behavior. She, being the romantic she was, didn’t want to ask over the phone for an answer, so she asked if they could get dinner the next night at the same restaurant. He agreed. The next night came, and he fully expected it to happen again. She asked him if he had thought about the previous night, and he immediately got nervous.

She asked if he had an answer. He ran to the bathroom and didn’t return. At that point, she was convinced he wanted to say yes but was just too nervous. She called again and scheduled a date two days later. She met him there, and as soon as he sat down, he said, "Yes". They proceeded to get married, and 30 years later, I am writing about my assertive mother and nervous father. Glad it worked out.

Failed ProposalsShutterstock

22. Crazy For Love

I had a girlfriend propose to me when we were on vacation for my birthday. I said yes, but once we were back home she melted down. She moved into her sister’s house with no explanation. Then, she took trips without me to visit and stay with men who were very open about the fact they wanted to get busy with her and didn't care if we were engaged.

At one point, she was in a completely different country than she told me she was. She returned after seven months of not returning my phone calls, emails, Facebook messages, messages left with her family, etc., and was surprised that we were no longer engaged. I still shake my head that I almost married a crazy person.

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23. No Coveting This Neighbor

When I was in high school, my best friend’s next-door neighbor told her that he was going to propose to me at Christmas. He was planning on buying a dozen roses and a ring. She told me about this, and I said it must be a joke. She gave him the information, at which point, he wrote me a note, asking me to think about it. I said absolutely not. I had never been alone in the same room with him and had only spoken with him briefly.  He was 19 and I was 15.

Failed ProposalsFreepik, wayhomestudio

24. This Proposal Was Impractical

When I was three years old, the neighbor boy—also three years old—asked me to marry him. Being the practical girl that I was, I told him I'd think about it. Twenty minutes later, when I went to his house to tell him yes, I found out that he'd already gotten “married” to the girl across the street. I was heartbroken until a couple of years later when I found out she was rather rough and liked to smack him around.

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25. Friction In The Food Court

I knew a guy who couldn't get over his ex. It was so bad that he didn't even think of her as “his ex”. She had moved on and already had a new boyfriend, and he wouldn't leave her alone. Then one day at the food court of the local mall, he approached her, in front of everybody, with a guitar and started singing. However, the song was just simple strumming, and "will you marry me" over and over again were the lyrics.

Plus, he started this serenade on the other side of the food court, so at first, nobody knew what was happening. So he got near her, and she realized that this voice she kept hearing was this dude—her needy ex-boyfriend. But the guy didn't consider one very important detail: Before she could get up or act embarrassed, her new boyfriend, who was buying food, dropped his whole tray and rushed at the guy with the guitar.

He sucker-punched him, then took the guitar away from him and started hitting him with it. All the while he was screaming, "Bro, I'm sick of you. You're too awkward", and stomped on his nuts in front of the play-pen/daycare center next to the hot-dog-on-the-stick restaurant. As a spectator, I can say the experience was super surreal. She did end up saying no.

Failed ProposalsFlickr, B Rosen

26. Hypnotized By Love

I once went to a hypnotist show. This guy was hypnotized to propose to his girlfriend with the girlfriend’s consent. She said yes after he gave a very honest speech about their relationship, but later, he woke up and forgot the proposal. Upon leaving the show, I saw her buying a recording of the show, and a few weeks later, she and her boyfriend came into my shoe store. I asked about it.

The boyfriend became beet red, and the girl laughed uncontrollably. They are not married but very much in love.

Failed ProposalsShutterstock

27. My Heart Was Dangling by A Thread

I was out with my girlfriend and one of her friends. Her friend distracted her while I got up on the roof of the building. They were standing near a large window when out of the sky, I rappelled down the side of the building and in front of said large window. When she saw me, I knelt down on the windowsill, which was somewhat tricky, and popped open the ring box. She cried, shook her head no, then ran down the hall. So there I was, dangling 60 feet up, with a broken heart.

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28. Post-Proposal Dessert

I saw a guy propose in a restaurant. They were there before us and had dessert on the table when he did it. When she said no, he got up and said, "Fine! Then you pay for dinner", and walked out. She sat there and ate her ice cream with a smile on her face. Then, she took his slice of cake home in a box. She didn't seem all that upset about it.

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29. Target Of His Affection

I used to work at the Target snack bar, and while working there met some of the strangest people. The weirdest, by far, happened one day when we were a little understaffed.  I was running around like a crazy person trying to keep the place running while my co-workers were all on break. I had just rung up a 30-something man and his elderly mother.

I was working on getting their food ready when he walked back up to the counter and proceeded to start up a rather awkward conversation with me. A few minutes in, he wound up proposing. I, of course, politely declined, but he was insistent that we marry or that I have a good reason why not. Although I was in a relationship, I knew that by itself wouldn't get him to leave me alone.

So, I told him that I was engaged. He looked disappointed but seemed to accept this, and returned to his seat. This nightmare wasn't over yet, though. A few minutes later, his elderly mother came up and started chewing me out about how I must think I'm too good for her son and how there must be something wrong with me, among other things. The absurdity of it all, combined with her very thick accent, made it so hard not to just crack up.

But somehow, I managed to get through without doing anything to make it worse. After I apologized for whatever inconvenience my rejection of her son had caused, she seemed satisfied and also returned to their table. Needless to say, it made things really awkward when I had to deliver their food a few minutes later! My co-workers never let me live that one down.

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30. Bad Timing

I was just barely 25, and he was 13 years older than me and recently divorced. I'd spent the two months we'd been dating making it clear I wasn't ready for a serious commitment. He proposed the night after my grandmother's funeral. As he started up with the proposal speech, I just started backing away and shaking my head.

There was no way I was getting engaged that quickly, or that young, especially given how much of an emotional wreck I was over my grandmother's passing. We ended up staying together for about another year. The night I decided I was ready to marry him, he didn't come home until 4 AM. I was pretty sure he cheated on me and we broke up shortly afterward.

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31. It Was A Sign From Above

I went to college at a small Mormon school in Idaho. I roomed with a moronic person who denied evolution and thought he was hot stuff because he wrote about sports in the paper. I had broken my arm on a motorcycle and on the 4th of July, he kept throwing a football at me. He was obsessed with his ex and would fight with her constantly until she stopped talking to him.

On the advice of our equally moronic Mormon Bishop, months after she had cut off all contact and was dating another guy, he decided to make the five-hour drive with a ring he took out a loan for to go and see her. She refused to see him, and then the engine fell out of his car, so another roommate had to drive down and pick him up sans fiancee or car.

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32. He Proposed On Facebook!

I turned my ex-boyfriend down. We hadn't really been dating that long but had been friends for a long time. He had just gotten accepted to law school in another country, and he Facebook messaged me, "I got in. I want you to have my babies! Marry Me"! He then sent me a link to an engagement ring site. I told him no, and his reply was, "I'm going to be a super-rich lawyer. What's the problem"?

We hadn't even been dating for six months. I'd have to quit my job, the degree I had just earned wouldn't be worth anything, and he'd been telling me the whole time that he wished I was smarter so that he could actually introduce me to his family. Apparently, that didn't matter as long as I had his babies.

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33. Wedding Day Dump

We had a wedding at a restaurant I worked at. It was a fancy place—like $150 a person—and there were 70 people at the party, so the father of the bride was really spending some hefty cash on the thing. The time for the ceremony came around, and the groom was nowhere to be seen. After about an hour, he finally showed up and proclaimed that he was gay and in love with someone else. It was a horrible scene.

The poor woman was devastated, but they didn't let that stop a good party; she looked pretty happy by the end.

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34. Their Dating Game Ended

When my friend was in college, he and his girlfriend at the time figured out a great way to get free desserts when they went out on dates at fancy restaurants. At the end of each meal, he'd propose, and she'd accept very publicly. Amidst the applause, as they were kissing, the manager of the restaurant would invariably go up to them and offer them a congratulatory dessert, gratis.

This worked throughout their time in college. I don't remember why their last date went the way it did, though. Maybe she was mad at him for something, or perhaps she was just in a pranking mood. However, on this fateful date when he got down on his knees and lovingly proposed, knowing that she would accept and, imagining the sweet dessert that was to come, he looked up with an honest, open smile on his face and saw her burst into tears.

She stood up, loudly declared that she didn't love him anymore, and ran out the door. The joke was on her, though. My friend said the whole restaurant felt so sorry for him that he got a hefty discount on the meal.

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35. Not What It Seemed

My cousin’s mom had an old ring and wanted him to find out if it was worth anything. He had a friend who was a jeweler, and he promised her a nice lunch if she'd take a look at the ring for him. They met at a restaurant, and she examined the ring briefly, only to find that the stone was not a diamond. Then, she had to dash. He took his time finishing his lunch, and a couple of times, he glanced up just in time to see the entire restaurant quickly avert their gaze.

Finally, a nervous waiter came up to him and said, "Sir, I'm really sorry about what happened. Can I get you anything from the bar? It's on us". That's when my cousin finally realized what was happening. A fellow was sitting alone in a restaurant that was a little bit fancier than he was dressed. A well-dressed woman hurried in and sat with him.

Halfway through the meal, he put a ring in front of her. She took out a jeweler's loupe, examined it, shook her head, and handed it back. Then, she had her lunch boxed up and left him sitting there. The whole restaurant thought they had just seen a hopeful young man get booted to the curb by the world's most heartless woman.

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36. No Does Not Mean Yes

I started dating a girl one summer while I was away from home for an internship. She had been seeing another guy before we met, and when he came to visit her at work, she told him that she was seeing someone new and that they were over. It had apparently been something she had been considering for a while. He left her store, went down the road, bought a diamond ring, brought it back, and proposed to her. When she said no, he flipped. She had to have security remove him from the premises.

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37. Friends No More

In college, I had a good friend who told me that he was in love with me, despite the fact that I had been dating someone else for about five years at the time. Needless to say, our friendship fell apart. He graduated that year, and I was still a sophomore. He didn't talk to me for about a year until one night, he showed up at my door and asked to come in.

He was well dressed, but I figured he was visiting someone and just stopped in to say hi. He said hello, and we exchanged a quick catch-up conversation. Then, out of the blue, he got down on one knee and whipped out a ring. He asked me to "take a chance". I was so flustered and confused that the first words that came out of my mouth were, “No, no, no, no, what"?

He looked like he had the wind knocked out of him. I just awkwardly stared for a few minutes before I burst out into tears. He asked to explain, and I asked him to leave. I kind of miss being friends with him, though. It sucks I had to pick, but it was really awkward.

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38. Looking For A Way To Stay

I said no to my boyfriend of a year. I cared about him, but our relationship had huge issues. This marriage business only started after he started having visa issues and was possibly looking at getting booted out of the country. He asked me while tipsy in a parking lot with a ring he grabbed at a pawn shop. I knew it was the wrong decision for both of us then.

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39. He Was Thunderstruck Down

I saw a guy get shut down at the mall; it was bad from the start. He was in a really old AC/DC shirt and looked like he'd been drinking for a week. Then, he dropped down on a knee out of nowhere, and she was holding hands with her 9-year-old son who was clearly from a different father.  He tried to yell and profess his love, but it was a weak attempt, and he just sounded like he was angry.

She didn't really say no in front of everyone, she just said, "Stand up. What are you doing"? He didn't get it at first but after 45 seconds of no answer he stood up and they walked away. I wish I could have followed them, but I was eating.

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40. A Scene From A Sitcom

My wife was dating a guy for a few months. It was nothing too serious in her eyes, and they were meeting to go out one night. It was one of those "sitcom" type moments, where they both said, "I have something I need to tell you". She said, "You go first", and he said, "No, you go first". Finally, my wife said, "I think we should break up". His reply was, "I was going to propose", and threw the ring at her. I tell her because the ring went in her direction, it technically counts as a proposal.

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41. He Was Sunk!

I had my grandmother's wedding ring and I took her out in a water taxi. I hired an acapella band. While we were in the middle of Baltimore Bay under the moonlight, I got down on one knee while the band started to sing our song "You Are Not Alone". I held out the ring and asked if she would marry me. She paused and some of the people were rooting for her to say yes, but she said no. I honestly think that was the last time I ever bothered to do something romantic for someone. It destroyed me.

Failed ProposalsPexels

42. A Leery Proposal

I turned down a marriage proposal once. A South African guy proposed to me in Barcelona at a Rotary International convention. I was sixteen. He didn't speak English, and actually, didn't speak at all. He just leered at me in a very unsettling way. So, his friend asked me and explained that I'd be a fourth wife. It was the only marriage proposal I ever got.

Failed ProposalsPexels

43. It Was The Right Move

I got engaged to my girlfriend of five years. We were living together at the time. About six months before the big day, she told me she wanted to move out until we get married. We had been under a lot of stress, so I agreed. I should have known a red flag when I saw it. Nothing was supposed to change, except where she lived. A month later, she didn’t want to go out on our normal Friday night date.

I began to question her and found out she had been "talking" to someone and was really confused. A couple of weeks after that, she was moving her stuff from my house to his apartment. Not only that, but this piece of garbage was still married to his wife. Two months later, they were engaged and she was pregnant with his child. It was the worst few months of my life, but I'm glad that conniving woman was out of my life.

Failed ProposalsPexels

44.  He Was Lip Syncing For His Life

I'm a karaoke host/DJ at this one club that gets a lot of crazy people in it. One time, I was working, and this guy came up to me and asked me if he could sing a song. He wanted to sing “Sweet Home Alabama”. So, I gave him the mic, and he asked me to leave a little bit of silence before his song, saying he wanted to make an announcement. I figure, what the heck, and let him. I regretted it almost instantly.

He went onto the stage and started doing this pathetic speech to his girlfriend, dedicating the song to her, then asking her to marry him. She says no. The crowd all booed, and started chanting, "Yes, yes, yes, yes, yes". She crossed her arms and shook her head. Her boyfriend was so embarrassed that he actually started begging her to—on the mic—on a stage—while she was saying no.

Everyone in the crowd started laughing and booing, and then he turned to me and waved at me frantically to start the music. He had to sing the song that he dedicated to her, in front of all the people who were making fun of him, after being rejected. I felt so bad for him, but who on earth dedicates “Sweet Home Alabama” to their girlfriend and proposes at karaoke anyway. She didn't leave the bar, but every single time I saw him try to touch her after that, she pushed him away and ignored him for the rest of the night.

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45. He Thought She Was Taking Him For A Ride

My grandpa went to a Catholic college that was men-only and my grandma attended the female-only Catholic school in the same town. The two schools frequently held social events. My grandpa fell for my grandma, and right as she was getting on a bus to leave for Christmas break, he asked her to marry him. She said no. She came back a month or so later, and they went on a few more dates.

Then summer vacation came and she was leaving for three months. As she was getting on the bus, my grandpa asked a second time, "Will you please do the honor of being my wife"? He thought changing the wording would be more effective. He was mistaken. She said no. Three months later, she came back, and she agreed to go on a few dates with him again.

Again, Christmas break rolled around and he was saying goodbye yet again at the bus station. He said, "You're a stubborn woman, but I'm a persistent man. Now if you reject me this time, I promise I will leave you alone forever. When you come back after Christmas, I promise you will never see me again. I love you and I want to spend the rest of my life with you. Will you marry me"?

She said no. As the bus began to pull away, my grandpa was rather dismayed. The bus got about half a block away before it came to a halt and my grandma pushed her way out the door, ran to my grandpa, planted a smooch on him and said, "I can't believe you believed me. Of course I will marry you". They lived happily ever after.

Failed ProposalsFlickr, Tony Alter

46. Holding Out

My grandma said "No" to my grandfather for six YEARS before she agreed to marry him. She wanted to be a nun. Her mother would invite him over for dinner and not tell her. He would find her at mass and sit by her in the pew, and every time he would see her it would be, "Hildy, will you marry me"? She would always reply, "No, Bruno", every single time for six years.

One day she finally said yes. They went on to have eight children together. Every time we ask her what made her finally say yes, she gives a different answer. I wish I could have seen his reaction the day she finally agreed.

Failed ProposalsPicryl

47. He Was Not The Apple Of Her Eye

My best friend and her ex had been broken up for months. They had just started talking again and they went to Medieval Times together with a big group of friends. About an hour into the show, her ex disappeared. No one knew where he was and she was feeling a little bit relieved, as he had been trying to kiss her all night.

Suddenly the lights came on and there was her ex in the middle of the ring in full armor. He got down on one knee and declared his love for her. Naturally, she kind of scoffed and said no. She got booed pretty hard for it too.

Failed ProposalsFlickr, One lucky guy

48. She Chose Lifestyle Over Love

After three years of building what I thought was a strong and wonderful relationship and planning a proposal for months, I got rejected on a deserted beach near Tulum. We had talked about it before and all indications were positive. As I was sitting there stupefied like I'd taken 16 Vicodin, she tapped me on the shoulder and asked, "Can I see the ring again"?

It was a great ring too, that cost me $19K after a hefty discount. She felt she "needed more time". I found out that her family had offered to move her to another state and pay for her to "find herself".  They were completely loaded—a private jet, many vacation homes, and a yacht. She wanted that lifestyle and knew I couldn't give it to her which, in the end, is understandable. If she hadn't led me on for three years, l could have spent them with someone who really loved me.

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49. Keep On Tryin’

My cousin's boyfriend has proposed to her three times. Once in private—she said it was too soon. Once in front of friends—she said he wasn't ready. The third time was at a family reunion (her family) in front of EVERYONE, and she said yes. The party went on for a while, and they left a few hours later. She gave him back the ring in the car and said she didn't want him to be embarrassed in front of everyone. This time, she flat-out said that she didn't want to marry him. I can't figure out why he sticks around. I'm sure he'll try again.

Failed ProposalsPexels

50. It’s Not Against The Law

As a teenager, I dated a real winner. He was terrible to me, and I stayed too long because I hadn't yet developed a sense of any self-worth at all. He proposed during my freshman year of college in front of my two roommates. He went on and on about how he was going to seek counseling and change, and everything would be dandy. I said yes because I thought I would spare myself embarrassment at the time and 25% of me believed it was possible.

The courage to break it off only came after I found out he cheated on me with some of my friends after the proposal. When I confronted him, he started bawling, threatened to take his life, and then informed me that an engagement was a binding contract and I had become his property, and I couldn't leave. I heard through someone later on that he actually tried to initiate legal action for dumping him.

Failed ProposalsPexels

Sources: ,


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