Marriage Proposals That Went Horribly Wrong

July 18, 2023 | Nia Williams

Marriage Proposals That Went Horribly Wrong

Proposing to the love of one’s life should be a happy and romantic moment; one that should be remembered forever—but not for these unfortunate Redditors. After much anxiety and planning, their dream proposals not only backfired but also took their souls with them. Others were greeted by downright cringe-worthy embarrassment. Just be thankful that these didn’t happen to you. 

1. The Wait

After seven months of dating, I proposed but she said no because it was too soon. I agreed and put the ring in a safety deposit box. I told her that if she changed her mind, it was there for her. I had no idea what to expect—but then, after two weeks, she said yes and we decided to have a long engagement period (two years) so that we could be sure. We've been married for 37 years.


Man holding engagement ring and proposingLook Studio, Shutterstock

2. Wake Up Call

We had been dating for two years and although we had ups and downs, I, at least, was happy.

After saving money for some time, I bought the ring and spent a day planning how I was going to pop the question. When the time came, I went down on one knee and asked. She flat-out laughed but said yes. I was overjoyed and euphoric. I put the laughter down to nerves or shock perhaps, but who cares? I was getting married!

The next day, since I was the first to get up, I took the dog out for a walk. When I got home, I found her putting the phone down. I asked if she had told anyone about our engagement, as we had agreed that we would be telling people together. She simply said that she had to talk to someone and dismissed it. I joked that it was her lover and she was having an affair. That’s when her face dropped and my heart sank to my ankles.

She then told me, quite plainly and calmly that yes, I had guessed right and that she was off to pack a bag. Three days later, she packed her bags and was gone. It was like she was never there. The witch tore my soul out and wiped her behind with it. To add salt to the wound, she ended up marrying him. That hurt immensely. It 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 came to women.


Man hiding an engagement ring ready to surprise his girlfriendSombat S, Shutterstock

3. You Win

My dad proposed to my mom the night they first met. They "bared their souls to each other" that night—talking for hours uninterrupted. And even though my dad wasn't looking to get married, he just knew. When he asked, she said no. He proposed again. She still said no but accepted another date. This went on almost daily for six months.

One night, my parents played Scrabble against each other for the first time. My mom loves Scrabble. She kicks people behinds up and down the block. This is a woman who takes pride in being well-read enough to serve as a quick reference thesaurus.

After a hard-fought game, she lost for the first time she could remember. My 105-pound 5-foot mother swept the board and pieces off the table, sending them flying across the room. She looked at my dad and said in a fury, "Fine, I'll marry you"! My dad responded, in classic male fashion, "Oh, I need to think about it".

He thought about it, and barely eight months after they met, my parents married in a tiny chapel in Vegas. They celebrated 23 years this year. 


scrabble board gameSuzy Hazelwood, Pexel

4. It Takes Balls

It happened at the ball game. He proposed while on the jumbotron. The text of his proposal appeared on the big screen and then it zoomed in on the couple. The scene had everybody cringing...hard.

The girl laughed and then you could see the guy’s dejected face. He started to slump back into his seat and looked as if he was going to cry before the jumbotron cut off. The entire stadium started to boo the heck out of the girl and people started throwing garbage at her. Security had to help her get out.

Man rejected when is proposing marriageAntonio Guillem, Shutterstock

5. A Whole Lot Of Nothing

My boyfriend and I went for a walk one day. He was visibly nervous but when he finally stopped, he very hesitantly said, "I've been thinking—of the long-term benefits of—marriage—or a marriage-type thing". He said that he had left the ring in the car but would pretend his wallet was the ring box. He got down on one knee and officially proposed. 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 scatterbrainedness were characteristic of him).

When we got back to our apartment, we 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, which lasted only half an hour and broke up. I took a very long drive and returned home 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.

One day, I had a boyfriend, a fiance, an ex-fiance, and an ex-boyfriend. 

Young man with engagement ring making proposalAfrica Studio, Shutterstock

6. Would You Like Some Cake With That?

I used to work at a fine dining restaurant and saw a few proposal rejections. The incident that stands out the most was of a guy who had the ring brought out with the dessert and proposed then. The woman seemed shocked and pretty annoyed at the situation and turned him down. One of the servers overheard her say, "You're not even my fourth or fifth choice".

Supposedly they had been on only a few dates and he just randomly proposed.

Handsome elegant guy is proposing to his beautiful girlfriendGeorge Rudy, Shutterstock

7. Let Me Think About It

She told me she had to think about the proposal. Two weeks later, she sent an email from Hawaii and rejected me.

Shocked man looking and reading email on laptoptommaso79, Shutterstock

8. The Longest Wait

I stayed home for three days. I didn't call her at all. I was only thinking about doing it. I finally went to her house, a little nervous. She thought I was coming over to break up in person, being the polite person she thought I was.

I sat her down and then asked her to marry me. She was shocked and said she had to think about it. It was the longest wait of my life.

Two weeks later, we went on what I thought was our last date. She asked me to ask her again. I did. She said yes.

Forty-one years later, with three kids, and six grandkids, having worked together in a business for 20 years, she’s my winning lottery ticket.

I'm glad she said, "Ask me again".

Young man proposing to girlfriendStudio Romantic, Shutterstock

9. You Crashed My Party

My mom and dad were in a car crash. Before my mom went in for X-rays, they first did a pregnancy test and discovered that 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 Valentine’s Day and already had a ring.

A week later, she accepted and they've been married for 22 years.


Engagement ring on bride’s handTranStudios Photography & Video, Pexels

10. I Kid You Not

We were in Ruby Tuesday having dinner. After I proposed, 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 that I was proposing. It wasn’t my proudest moment, but luckily it all worked out.

Men proposing marriage to his girlfriendScott Webb, Pexels

11. Message Received

After four weeks of dating, he got down on his knee with a HUGE diamond ring. He made an endless speech along the lines of "When you know you know. Will you marry me"?

Since I barely knew the guy, I flat out said no, followed by "Sorry—are you okay"?

He didn't speak to me for the rest of the night. When he dropped me home, I told my roommate about it. As I was telling her, I got a text from him—yes, a TEXT. It said,  "You've broken my heart. I never want to see you again. Goodbye. I love you".

We were both 22 at the time.

Woman rejecting a marriage, Shutterstock

12. Awkward Silence

I saw a guy get turned down at Universal Studios City Walk. Everyone cheered and was happy for them. Then she said no. The silence was deafening. He got up, brushed his knee off and they both walked away quickly

Portrait of a smiling man proposing to a girl with flowers and an engagement ringDean Drobot, Shutterstock

13. Not A Surprising Outcome

I was raised in a traditional Indian home and I am not the least bit traditional myself. My parents thought it would be a good idea to send me to a marriage convention. I decided to go so that I wouldn't have to deal with any unnecessary drama.

When I got there, I went to the first girl I saw and asked her to marry me. But she said no.

Indian man giving ring to womanDeepak Khirodwala, Pexels

14. Just A Dream

I took my girlfriend out to an island in Boston Harbor to propose with a view of the entire city spread before us. She said yes. We then spent the rest of the beautiful day together. When we returned to our warm, bright apartment, my head began to fill with dreams of a shared house, children, and a future.

Three months later, she told me she had fallen in love with her soulmate—a married man she met at her internship. For three months, I tried to make her see my love for her by waking up early every morning to make her breakfast, and having date nights every weekend, and in the end, she still chose him.

Man proposing marriage to his girlfriend at beachNAK Photographer, Shutterstock

15. This Isn’t A Dress Rehearsal

I am an emcee for live-stage events. I have been asked to be part of many proposals, but for some reason, very few go through with it. Only about one out of ten 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 proposal went badly, and I'll never forget it. It was at a cosplay contest. I recall the guy got on one knee and proposed. The stunned girl said nothing, shook her head, and ran off. Then the guy's costume (a kind of "medieval rogue" or Robin Hood-ish affair) had to stand up from one knee but his boots were too tall for his legs (either that or he stepped on his cape). He pitched to one side and fell over. Then he got up and left.

The audience went silent. I didn't know what to say, so I just went onto the next contestant and pretended like it never happened. Later, at the after party, the judges and the staff were all gossiping about how horribly awkward it all was. One of the judges admitted, "I almost fainted from embarrassment in sympathy".

Woman refuses the engagementevrymmnt, Shutterstock

16. Not My Fairytale Ending

We were together for over eight years and everything seemed fine. We talked about jobs, housing, kids, and having a future together plenty of times. She had shown me rings and we talked about weddings so it felt like it was time to finally propose. 

I went and bought a ring, and tried planning some neat trips to take her on for an awesome proposal. Finally, I decided I was just going to do it around New Year's, but right before that, she bailed. The timing was just so perfect for her not to have figured it out. But she somehow knew. I never really got an explanation, just the general, "I love you but I'm not in love with you".

We tried to maintain a friendship for a while after that but it was super hard for me because I was still totally into her. I had to drop off the map entirely for a year or so because we shared the same social circle and I just got so incredibly uncomfortable around her. Not where I expected to be at this point in my life.

Desperate African American Man Holding EngagementProstock-studio, Shutterstock

17. What An Entrance

I work at international arrivals in an airport and daily, see joyous reunions that are so filled with love, it makes me nauseous. (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 all of a sudden I heard a trombone playing. I've seen people play guitar, ukulele, saxophone, and one time a drum set but I've never heard a trombone in international arrivals

So the song started and I recognized the tune—it was the Imperial March from Star Wars. I was confused as ever and tried to find out where the heck it was coming from. I scanned the crowd when I suddenly saw this girl whose face was beet red. I immediately assumed that she had something to do with whatever the heck was happening, so I kept my eyes on her.

She ended up walking up to the guy who was playing the trombone. When he finished up the song, he passed his trombone to the person next to him (I'm assuming it was his friend), and then got down on one knee. The girl was about 25 feet away from me, so if there were words exchanged, I didn’t hear them. But, what I did see was the guy smiled, then suddenly looking dejected, stood up and walked away from the girl while she just stood there with her face still red like a tomato.

That was super awkward to watch.

Young woman rejecting marriage proposalAquarius Studio, Shutterstock

18. You Stubborn Brute

My dad proposed to my mom after they'd been seeing each other for just under two weeks. She laughed and told him he was looney, that it was way too soon. My dad said—and he is very proud of this fact, "Fine. I asked you once. I'm not gonna ask again". My mom thought he was bluffing. 

After a year of dating, she started giving him a hard time about not asking her to get married again. He didn’t budge from his original stance and said she missed her chance and that he wasn't going to ask again. 

My mom finally broke down and asked him to marry her. She also made sure she ridiculed him thoroughly when she did it, too. She made a big show about asking his father for permission, got down on one knee in public, and got him the gaudiest engagement ring she could find. He said yes and they just celebrated their 30th anniversary.

Woman proposing marriageGround Picture, Shutterstock

19. Kick In The Teeth

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. Eventually, she did do that three months later and ended up marrying some other dude within 18 months.

The real kick in the teeth, however, was that I 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 with nine friends and go chuck it into a volcano.

engagement ringLeah Kelley, Pexels

20. That’s A Lot Of  Hot Air

It was my mom's birthday and she wanted to go on a hot air balloon ride. These rides are done in groups with other strangers in the basket.

While on the ride, a man proposed to his girlfriend. He got down on one knee, pulled out the ring, and popped the question. How did she respond? Well, she said something like, "You've asked me this three times already. Did you think that taking me up on this balloon would change my answer”? 

My mom said that it was pretty awkward for the rest of the balloon ride, so I can imagine that made the experience even worse.

woman turning down engagement proposalfizkes, Shutterstock

21. Get Me Outta Here

It was pretty packed when we walked down the beach like we normally did. An airplane flies by with a banner saying, "Tiffany, will you marry me? -Tom". Well, my girlfriend just screams, “Yes”! Then hugs me. I was like What the… and stared at the sky not even realizing she had her arms around me. She looks into my eyes and finally figures it out. It was the quietest, longest, most painful walk home of my life. I wish someone would drown or a boat would explode on fire to change the mood.

What a messed up coincidence. It was pretty brutal, but she took it ok.

Yeti studio, Shutterstock

22. So Unexpected

I used to work in a fast-food restaurant. One day, a regular came in and asked me if I could come into the dining room to talk with him. Since I knew him pretty well from waiting on him for five years, I thought sure. So he asked me to sit in the booth where he then told me how nice and pretty was. He said that I seemed like a person who has an open mind and does not judge. This is when I started to think...something is not right. He then proceeded to ask me to marry him.

He gave me this long story about how he thought I was trustworthy and he had been living in this country for years and it was going to take him a long time to get citizenship. I told him I was flattered but that I had a boyfriend and things were serious. He then tried to proposition me by telling me I could still stay with my boyfriend and he would pay me and buy me presents. Once again, I politely declined him. 

He was super bummed and from then on when he came into the restaurant, he would always ask if I had gotten married yet. It started to get annoying. So one day, I started wearing a ring and told him my boyfriend and I tied the knot.

girlfriend rejected his marriage proposalGligatron, Shutterstock

23. Hide But Don’t Seek

I spent Easter with my boyfriend’s cousin. He was probably around 24 at the time. He decided to stash a ring for his girlfriend in an Easter egg and wanted to send her out on an egg hunt.

He spent all morning planning it out and putting people in charge of snapping pictures, popping champagne, etc. When his girlfriend got to the house, he told her she had an Easter egg hunt to go on. Her reaction startled him—she got upset, saying that she was tired and didn't want to "do that garbage". He finally broke down and said, "There's a really special thing in the egg that I know you'll be excited to find". She then said, "If it's a freaking engagement ring, the answer is no".

That was painful to witness.

lady not willing to accept engagement ringProstock-studio, Shutterstock 

24. Brutal Misunderstanding

A friend gave his 10-year on-again-off-again girlfriend a ring for Christmas. I'm not quite sure how the conversation went when she opened the gift. She did, however, post on Facebook that it was an engagement ring and that they were going to spend the rest of their life together.

The picture and update got hundreds of likes. After calling my friend to congratulate him (he didn't have Facebook), he was confused as to what the congratulations were for. After he learned what his girlfriend had posted on Facebook, it was apparent that he was irritated that she thought it was an engagement ring. He got off the phone with me rather quickly to call her. The picture of the ring and the status update disappeared not soon after.

Man propose marriage to girlfriend in pink, Shutterstock

25. A Weekend To Forget

I used to work at a jewelry store in a small town. I had a kid come in that was roughly 22-24 years old. He came in with his younger brother. The kid was excited but the younger brother was apprehensive and made comments that would hopefully cause the kid to reconsider.

I rang him up for a $1500 ring and told him before the sale that there were no refunds, and that it could only be returned for in-store credit. He didn't blink or hear me and said, "OK"!

That was on a Friday. On Monday, he came back in with a black eye and asked for an exchange for the ring.

I felt horrible for him.

diamond engagement ringFOX, Pexels

26. No Regrets

I was saving up for a ring. I had planned to propose to my girlfriend but got cheated on the day before I went to buy the ring. I bought a huge bong instead. No regrets.

man in red shirt thinking somethingAndrea Piacquadio, Pexels

27. Unexpected Outcome

I overheard her on the phone saying that she was worried that I was going to propose and that it was time to end it. After the call, she ended it right then and there. I had already bought the ring. When I went back to the shop to return it, I kind of broke down trying to explain why I had to return the ring. It was the lowest moment of my life—but also the greatest. That's because the girl at the counter demanded that she take me out for drinks that night. We had a great time laughing at my whole situation. 

Three days later (today), the shop girl left me a message asking if I wanted to take an impromptu trip away with her over New Year's. I’ve been staring at the message all day now.

ring in the boxRuslan Grumble, Shutterstock

28. Young Love

I was a young, stupid 21-year-old in love, or what I thought was love. We had been dating for three years. It was a rocky relationship. She was using me to boost her self-esteem and I was too stupid to realize that a relationship shouldn't reduce me to tears every week. 

Anyway, we were fighting in a Bank of America parking lot and I was sure she was going to leave me. So, out of desperation, I screamed, "Just bloody marry me! Let's get married"! Well, she agreed and we planned on getting married the following month.

I was pretty excited and convinced myself that I had found my soulmate. I spent a stupid amount of money on an engagement ring and gave it to her that weekend.

We decided to take a bath together. As I was behind her, giving her a shoulder massage, she decided to tell me that, quite plainly, she had cheated on me with three separate guys that month. Without a word, I stood up, stepped out of the tub, and pulled my jeans over my wet legs. I walked out of her house, drove away, and didn't speak to her again—that was six years ago. I'm still a shell of a man because of it.

Woman refusing engagement ringfizkes, Shutterstock

29. Beyond Heartbroken

I dated a girl for almost two years. She was my best friend. I loved her to bits and we always had fun together.

Last December, I took up a new job that was much higher paying so that I could provide for our future. With the first salary, I bought a diamond engagement ring and on the 12th of January this year, I proposed. She was shocked, but she said, "Let me think about it". I gave her space after that but the answer eventually came to a "No".

I’ve been heartbroken ever since. I haven't been able to date anyone else for almost seven months and think about her a lot. I can't change that too much, I guess.

Young woman rejecting marriage proposalPixel-Shot, Shutterstock

30. I Proposed To The Devil Itself

I was with a girl for just over five years. When we met, she was in a bad place. The guy she was with before I used to hurt her. It was brutal. So it was tough in the beginning because she had major trust and self-esteem issues, depression and she self-harmed. But I went and fell in love with her. I helped her get over a lot of the mental anguish she was going through. I even took her to (and paid for) her therapist every other week. We lived together for four of those years.

On our fifth anniversary, I proposed. I was madly in love with her, and I assumed she was with me. She said yes!

Then, a few months after that, I got off work a bit early. I picked up her favorite fish and chips for dinner and headed home. Little did I know my life would change as soon as I walked through the door.

Long story short, I walked in on her with some other dude in our bed. They didn’t even hear me come into the apartment.

Within two days of that happening, she was gone. All her stuff was out of the apartment. She took half of MY stuff as well, including my cash stash of several thousand dollars, my TV, and a bunch of my kitchen stuff, she kept the ring. But she took my freaking DOG man. Took the dang dog.

I haven't seen or spoken to her since. That was just about three years ago now.

Australian Shepherd dog in a parkHelena Lopes, Pexels

31. Stop It Already

One of my students in the fifth grade has proposed to me three times now. The first time was with a Cheerio. The second time was with a cookie. And the last time was with a piece of tape. I said no, flat out, all three times. Like, okay, cute—whatever. But DANG this kid is annoying. I'm standing there, trying to teach you how to find the least common multiple so you can order fractions, and you're proposing to me? Finish this problem dude, you're the only one here who can't do this. I'm trying to help you. Flipping listen instead of letting your little 10-year-old mind go to a weird place.

Teacher and studentsTima Miroshnichenko, Pexels

32. Boy, Was He Wrong

I was in the third 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. I guess he was hoping that the pressure from being in a classroom with a bunch of kids would pressure her enough to say yes. 

Woman gesture rejects the proposalYeti studio, Shutterstock

33. Shocking Revelation

I proposed after three years of dating and one year of living together. I was offering her my great-grandmother's wedding ring. She said no. That was Friday night. By Sunday night, after a trip to her parents, she came back and told me that she was into women. That was 22 years ago.

Since then I have been married for 16 years to the next woman I dated. My wife has the wedding ring that I offered to my ex. Her girlfriend has been with her partner for nearly 22 years. I have a daughter and they have a girl and a boy. I love them and they are just the best people ever.

Girl refusing engagement ringfizkes, Shutterstock

34. That’s Reel Life

My dad proposed to my mom after dating her for a couple of years. She turned him down and they broke up.

After some heart-wrenching months for my dad, my mom's father passed on. My mom needed consoling and called my dad up. They dated for a few more years after that and mutually decided to get married.

Needless to say, I freaked out the first time I watched High Fidelity. That movie is essentially my parents—except my dad doesn't take mixtapes.

Indian woman refusing to take engagement ringProstock-studio, Shutterstock

35. Persistence Doesn’t Pay Off

One time, I was eating at a high-end restaurant with my girlfriend. We saw some guy two tables down go down on one knee and pop the big question. 

I remember just sitting there—amazed. I thought, wow, I’m about to witness something wonderful—something unique—something pivotal in a young man’s life. Nope. The girl declined him. 

He stayed on that knee and kept asking why. The girl, who was super embarrassed by now, directed him to get back up—but he started sobbing. Everyone sitting around him started encouraging him, "Get 'em next time, little buddy"! or "Never mind her, champ"! 

It was so awkward.

Woman Refusing Marriage Proposal From Her Boyfriend At Romantic Dinner In RestaurantProstock-studio, Shutterstock

36. You Broke My Heart

I dated my ex from the ages of 14-24. She just broke up with me six months ago.

By the time I was 16, I was sure I wanted to be with her for the rest of my life. I saved money from my part-time job for a few months and got the nicest ring I could afford at Zales. I took her up to Hook Mountain, a place near where I grew up with beautiful views of the Hudson River. I knew she loved me, and I wasn't nervous—but knowing what I know now, should have been.

I don't remember exactly what I said, it's become a blur in my memory. But she was scared as heck by my proposal. She told me she loved me, but she was nowhere near ready to commit to me. I was sad. We left the trail and got some ice cream. I didn't talk much. I returned the ring and never told anyone about it—not my friends, not my family.

We've been broken up for six months now and I still think about her every day. I still love her deeply. I think I probably always will.

Man begging a woman for lovewk1003mike, Shutterstock

37. Not Good Enough

Her family had this tradition: the parents would hide a pickle ornament in the Christmas tree and all the kids would race to see who could find it first. The winner got an extra present. So I asked my girlfriend’s parents 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. I haven't spoken to her since. Four years and all my love weren’t good enough, I guess!

Young attractive woman is refusing a wedding ringMy Ocean Production, Shutterstock

38. Close Call

I was dating someone for four years. After two years, she had already wanted me to marry her. I was unsure about it until she made it known how much it would mean to her. I had never seen marriage as necessary for a good relationship. It just seemed to be complicated paperwork. But I decided to do it. I bought the ring and kept it for a few weeks to plan how I wanted to give it to her. Then I found out that she cheated on me because I took too long to propose. I wanted nothing to do with the ring after that and threw it in a dumpster.

After four years, she missed marriage by five days. She even found out the day I was going to propose because I had the day off from work to set things up. 

Man Proposing Engagement Ring to his girlfriendVGstockstudio, Shutterstock

39. That Hurts

I was dating a girl for a while. We went on a walk one day and I got down on one knee. I took her hand in mine. Tears welled up in her eyes. Then I asked, " Will you—will you wait for me to tie my shoe"?

I’ve never been slapped so hard in my life.

Horizontal shot of young man in casual clothing standing on one knee and holding engagement ringAnna Tryhub, Shutterstock

40. Missing You

I had been with my girlfriend for over two years but we had known each other for a couple of years before that. We had talked about marriage. We both agreed that we wanted to get married but wanted to wait for her to finish grad school first.

When she graduated from Purdue, she moved to Penn State at the beginning of September 2012. Her family is old fashioned so I didn't want us to live together before being married. So I stayed in Indiana.

We spoke every day. We managed to see each other a few times when she was in the tri-state area. We both planned for almost a month for me to come out to Penn State and spend a week together. Before the trip, we talked every day and everything seemed fine. I worked extra shifts for a month straight to save money and got her a ring. I know we had talked about waiting, but I wanted to give it to her as a token to show that the distance wasn't too much for me and that I loved her and would continue loving her. After the twelve-hour drive, I finally arrived at her place. We spent a lovely day together and then it was time for bed.

Given that I'm an insomniac, I lay in bed next to her for a while. Eventually, I asked if I could use her netbook to browse the internet until I fell asleep. She said I could, so I turned it on and logged into Windows. Skype's window was flashing. That's when my heart dropped—I saw a conversation with her ex-boyfriend—months of conversations. 

He had come out to see her less than two weeks after she moved to Penn State and they had slept together. I woke her up. We argued for a few hours, then I drove home. During our argument, I threw my luggage out the sliding door and into the yard. The pocket that had the ring in it was unzipped. I somehow managed to lose it somewhere in her yard and didn't realize it until I was back in Indiana.

I also had to say goodbye to a dog that I had raised from day one to a year old. I brought her to my ex as my roommate had a sudden issue with dogs.

A bit over a year later, and I still miss that darn dog.

Young couple arguing at homeAfrica Studio, Shutterstock

41. Gone But Not Forgotten

After returning home from a Christmas vacation together, I asked her about marriage. She said, "I don't want to marry you. I never wanted to marry you. I will never marry you". This was followed with a thirty-minute speech about missing her single life.

I broke down inside, honestly. I tried to make it work but I realize now I stopped trying after that. Eight months later, she moved out. Three months after that, she begged me to take her back and that she wanted to get married and own a house. I was just too hurt to believe her.

Therapy is helping. But a five-year relationship ended that day. I miss it, but I'm not sure I miss her anymore.

Unhappy, upset, angry, mad woman refuses apologyVoyagerix, Shutterstock

42. My Soulmate

My friend's parents met at a bar down the shore. Her dad was crazy about her mom, but it was unrequited. She slept with him anyway. It was just a one-night stand, then she ignored him after that. That is until she found out she was pregnant.

He was over the moon when he found out. She was intent on having the baby. He tried to be with her, but she consistently refused him. He proposed to her several times, ending in eye rolls and exasperated "No!" from her each time.

After nine months, she went into labor and let him come with her into the delivery room. Just her and this guy who had been begging her to marry him. A few hours into labor, the doctors started to notice something was wrong. The baby's heartbeat was slowing rapidly.

The mother started to panic, but the father stayed calm. He stayed with her and communicated information from the doctors. But there was little anyone could do. She delivered a stillborn.

After everything that happened, my friend's mom realized she had found her soulmate. They finally got together and are still married to this day.

Confused african american woman in doubt looking at engagement ringProstock-studio, Shutterstock

43. Worst Timing Ever

My good friend was dating this guy for nearly two years. I could tell that things were getting a bit stale with them. One day when we went out to get lunch, she told me that she was going to break it off with the guy. She seemed far more stressed about hurting him. She started telling me about how she was going to do it and was asking for my advice.

Right as I was in the middle of giving her some input, the guy came in and looked a bit frantic. She must've told him that she was going there to meet me. He mustered up the courage and walked right to our table, completely ignoring me. He got down on one knee and pulled out the ring. He was shaking so much. I was in awe of the worst timing ever, and my mouth was open in shock. People around me were excited so everyone gathered around the table started cheering. The guy proposed to my friend. She just got up, walked out to her car, and drove off.

I almost perished from second-hand embarrassment. All I remember was gasps and snickering from the people near me and he just sat in her place looking crushed. I didn't know what to say. I feel kinda bad so I just got the check ASAP and gave him a pat on the back.

Girl Gesturing Stop To Offered Engagement RingProstock-studio, Shutterstock

44. What A Load Of Garbage

I'm a male, and I was in a relationship for some time with a guy. I suspected that he was cheating on me with his ex for some time. While I was away for a few months on a trip to Italy, my best friend sent me pictures of my boyfriend and his ex kissing at a bar. Surprisingly, I remained calm—because I knew exactly how to get my revenge.

The next day, I bought the ring and flew back to the US. After I landed, I proposed to him at the airport gate. He said no and I asked why not. He said it was too early. I showed him the picture of him and his ex and asked, "You sure it isn't because you're a sack of garbage"? I took the ring back and he moved out two weeks later.

Portrait of a satisfied happy man dressed in tuxedo holding open box with an engagement ringDean Drobot, Shutterstock

45. Perfect Setting For A Letdown

I dated this girl off and on for 12 years. Most recently, we had been together for six years. We were on a trip together in the Philippines and swimming in this beautiful lagoon. That’s when I decided that it was the perfect setting to propose. I began with, "Hey, baby…" and she must have heard it in my voice because she turned around and said, "Don't do it".

That took the wind out of my sail real quick. She eventually said yes a few months later in Australia.

Man hiding a ring behindTWStock, Shutterstock

46. What A Waste

My then-girlfriend proposed to me on the leap day of 1992. I said no—I was too young to know better. We went our separate ways but came together again. We’ve now been married 19 years. The result of saying, “No” was five wasted years! 


man rejecting marriage proposalPixel-Shot, Shutterstock

47. Out Of The Blue

A few years ago, I worked on a cruise ship in the main dining room. You tend to work in the same area with the same five people every night. One such co-worker 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 about how I would like to start something a little less playful and a little more serious. As 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 we were still playing around.

Turns out it was very real. She offered to pay me $3000, 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 our contract. I’d like to think it was because she was heartbroken, not because I wouldn't help her get citizenship. But either way, I felt terrible and kind of amazed that someone proposed to me!

Caucasian man in red checkered shirt refusing somethingAsier Romero, Shutterstock

48. Where’s The Romance?

My parent's engagement story is the least romantic one I've ever heard. They'd only been dating for five weeks at the time, and my dad, without giving her a ring, asked very casually if she’d marry him. For some reason, she said, “Yes”.

By the way, this didn't go down at a romantic fountain or over a classy dinner it couldn't have been any more opposite. It happened in my dad's truck right before he dropped her off at home after their date. There was no kneeling, no ring, obviously not much thought put into it. And she still said yes. He then called her the next day to say that he'd been thinking about it, and he wanted to take back his proposal.

A few days later, he changed his mind again and proposed for a second time. Even then, she still said yes. I don't know how a couple with such a horrible engagement story has lasted 26 years but they are still what everybody calls "the cutest couple". 

man asking his happy girlfriend to marry himsivilla, Shutterstock

49. Say Cheeze!

I flew to Wisconsin from Texas to surprise her for her college graduation. I told her all along that I couldn't make it only to surprise her. I arranged for 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.

I got down on one knee and she said yes. We went out to dinner that night and that was when the truth came out. She told me that she had only said yes because of all the people who were there.

Seriously, don't propose in public. That was the worst part. I foolishly stuck around for another year and a half before breaking up. 

man in love putting wedding ring on his woman fingerProstock-studio, Shutterstock

50. Duped

After I proposed, she told me that she couldn’t marry me because she was engaged. For three years while we were together, she was dating someone else the whole time. 

Woman Refusing ProposalNicoleta Ionescu, Shutterstock

Sources: Reddit,

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