Engagement Horror Stories

Engagement horror stories

Join us for a rollercoaster ride of unexpected twists, mishaps, and heartwarming resolutions. Don’t miss out on the drama and delight!

Proposals of Cringe and Chaos

We’ve all dreamt of that picture-perfect proposal: the twinkling lights, the romantic ambiance, and that joyful tearful ‘yes’ moment. However, the path to forever isn’t always paved with rose petals and fairy lights. In the world of engagements, these bumps can sometimes turn into full-blown horror stories. From unexpected drama to literal bloody messes, engagement stories can take unexpected and often comically disastrous turns. Join us as we delve into the world of engagement horror stories found on Reddit, where the path to “happily ever after” can be filled with twists, turns, and plenty of laughs. 

Restored Diamond Engagement Ring Displayed on Rock Near Ocean Engagement Horror Stories Featured Image

“I had gotten the ring, and was thinking about the logistics of where in our apt I could hide it that she wouldn’t stumble across it. I wanted to make a big presentation of the whole thing and was trying to come up with a good plan.

My mom was with me at the time because I value her opinions when it comes to jewelry, and she said ‘you know, sometimes it’s more memorable to make an average moment special, then to make an event out of it.’ So when I got home, I started changing clothes, and the GF came home. I dropped down on one knee and gave her the box. She lost it. That’s when I realized I had not yet put on pants.” – Redditor Parker2010

“I’ll start by saying we’ve been together for 3 years. We have a great relationship and he’s a wonderful father to our child. The proposal really came out of nowhere. I was in the bathroom getting ready to take our little one to daycare, which we were already running late for.

Restored Sapphire Diamond Gemstone Engagement Ring Displayed

My boyfriend walked in behind me and held a ring up in his hand and just said ‘Will you marry me?’ I honestly thought it was a joke and the ring was simply a gift. I laughed, said yes, put the ring on and left.

When I got home and spoke to my boyfriend, I realized he actually did ask me to marry him. I would’ve said yes either way (if it was a joke or not) but I was just left feeling a bit.. disappointed and empty, I guess.

I’m not the biggest fan of the ring either. It’s big and chunky and uncomfortable to wear. It was meant to be sapphire to match my birthstone he said, but he ‘accidentally’ got the wrong colour. It’s not my style and it doesn’t suit me whatsoever.

We’ve never looked at engagement rings together so he wouldn’t know what I like. I mentioned this to him and asked if he would mind if I bought a smaller ring (with my own money) to wear instead but he got quite offended by that and called me ungrateful. He’s been moody ever since. May I add that the ring he bought wasn’t expensive, so it’s not like he’d be wasting lots of money if I didn’t wear it. (Price doesn’t matter to me.) 

I wasn’t expecting a grand gesture or huge proposal.. but a little effort would’ve been nice, not just asking me in the damn bathroom. It’s meant to be a special moment and memory and it’s just.. Not.” – Redditor Throwawaybbz89 

“I decided to propose to my gf of three years on our third anniversary. I flew her to Vietnam and after a couple of weeks travelling we ended up in Cambodia. She had wanted to see Angkor wat and some other temples that were on her bucket list.

After a long day of hiking in the heat through ruins we retired back to our hotel and when we were alone together I proposed and she said yes. We kissed and I had planned to take her to the waterfall the next day to celebrate. It’s really beautiful.

She took a shower and I laid in bed thinking what an amazing day I just had and how I would get to spend the rest of my life with the women I loved. When she came out of the shower however she was in tears.

She handed me back the ring saying she couldn’t accept it because she didn’t want her memory of my proposal to be in a hotel room.” – Redditor zenmonkey99

Restored Diamond Gold Engagement Ring Left of Hotel Counter

“My fiancé and I [have] been dating for 2 years, he honestly been the best boyfriend and support person in my life. […] My fiancé been married before but his wife unfortunately passed away due to someone driving under the influence, my fiancé and my fiancé’s family both described her as an amazing women who was basically a saint. Sometimes I feel like I am compared to her and even get comments from my fiancé family members that I look and sound like her, it sometimes makes me if little uncomfortable because I’m not her replacement. 

I always knew that my fiancé kept some of her belongings, including her engagement and wedding ring and I always been okay with it but I never expected for him to actually propose to me with her ring. 

Restored Diamond Gold Engagement Ring Displayed in Proposal Box in Dim Room

When he proposed he organized a family picnic to announce my pregnancy and honestly I never seen a picnic so fancy before, everything was perfect my and his family were both there but when he proposed I seen that the ring he chose was his deceased wife’s ring and I was a little taken back I hesitated before I said yes and his sisters and mom noticed.

Later on his sisters and mom questioned me about it as if they were some kind of interrogators and I was honest, I told them I felt a uncomfortable being proposed to with his deceased wife ring and I felt that it belonged to her and not me. 

They told me that my fiancé wanted to pick a meaningful ring and nothing spoke to him but his deceased wife’s ring. I answered back saying that I would’ve been happy with any ring even if it was a freaking ring pop candy but something doesn’t sit right with me being proposed to with his dead wife’s ring.” – Redditor I-Dont-Know-Nothing1

“I had been dating this girl for about a month or two while we were in college, and we lived close enough in the summer to see each other frequently, so I was over her house and we were getting stuff ready to grill out when a car pulled up.

We assumed it was some of her friends, who we had invited, just arriving a little bit early. She peeked out the window and gasped. […] ‘it’s Matt!’ Matt was an ex-boyfriend from high school. They broke up senior year, but he had been pursuing her since then despite constant outright rejections. ‘Do you want me to take care of this?’ I asked. ‘No, I’ll deal with it. He’ll just try to start a fight with you.’ So I sat by the window and watched the whole thing. It was short.

He said that he wanted to talk. She said she really didn’t want to talk, she was having people over, and besides, they had talked everything out a while ago and everything was settled. There was nothing more to talk about. He was a [bad] boyfriend, it was three years ago, she moved on, he needed to do so as well. 

That’s when he doubled down.

‘I know the reason we’ve been apart. We were in high school. We were kids. We weren’t adults. So you can’t ever see me as an adult. Not until I man up. You need to know that I’m serious about this. That’s why I have this!’ 

He got down on one knee and pulled a ring box out his shirt pocket, just like a jewelry commercial. He opened the box and said, ‘Beth, will you marry me?’ She tried really hard not to burst out laughing, but only halfway succeeded. ‘OH MY GOD, NO! GO AWAY! There are people coming over, Matty, don’t embarrass yourself any more than you already have. Seriously, just go!’

He had this quizzical look on his face, like shock and disbelief. He really thought this was the right play. After a few seconds, he got up, put the box back in his pocket, and walked back to his car without saying another word. 

She came back inside. ‘I can’t BELIEVE that just happened,’ she said in a mixture of amusement and anger. I was mostly on the side of amusement, so I asked if the ring was nice. ‘It wasn’t even a ring! It was a tiny note that said ‘Any ring you want.”” – Redditor urge_underkill 

“I unfortunately didn’t witness it, but my best friend just got engaged and when her SO proposed they were in a little French deli.

She had just put a massive mouthful of pie in her face when she saw he had got down on one knee. She was so shocked she spat the pie out all over herself, all over him, all over everything.

She just sort of nodded … it was very like her to do something like that so it’s all fine but still … I don’t think he was expecting pie in his face.” – Anonymous Redditor

“This morning I decided to surprise my girlfriend with a proposal in bed. Not the most original or romantic approach, I know. Initially the plan was to pop the question over dinner last night, but alas, the build up towards the big moment got the better of me. However, today I woke up determined to do what needed to be done. 

So, there I was, on one knee next to my girlfriend’s side of the bed, waiting for her to open her eyes and see me holding the ring. The moment I attempted to wake her up she groaned and rolled over, leaving me with nothing to look at but the back of her head.

My heart was beating hard enough to hear. I leaned over my girlfriend and gently tapped her on the shoulder.

Instead of waking up like a normal person, she hissed in her sleep like a […] vampire before elbowing me in the face. I stumbled back and dropped the […] ring.

My girlfriend woke up during the commotion and the first thing she saw was me bleeding from my nose. Not gonna lie, when she rushed over to comfort me I flinched. The hissing thing she did scare […] me. After all the drama died down, I managed to recover the ring without her noticing. Speaking of recover, my nose still hurts.” – Anonymous Redditor 

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

She flips…. Ohmygod! […] Yes! 

He says “great!” then hands the ring back to the employee and tries to leave the store. He proposed with a borrowed ring. Tries to explain to the girl he couldn’t afford the ring but wanted to propose correctly. She slaps him so hard my face hurt […] and starts screaming about how her mother was right.” – Redditor kemikiao 

“I am recently engaged and was kind of disappointed because he didn’t consult me at all when ring shopping. I don’t wear rings normally, didn’t collect pictures on Pinterest. He really had nothing to go on and he has a tendency to be very confident in thinking he knows what I like/want when he’s usually not. Like birthday/Christmas gifts he gets so excited because he’s SO SURE I want it and will love it, but I don’t always. And it’s my fault for never correcting him because I don’t want to make him feel like I don’t appreciate his gifts. 

Anyways, we’d been together a long time but never directly talked about marriage. I tried to coax it out of him but he was always vague but seemed to intend to marry. Eventually I just broke the ice and we began to talk more openly about it.

I waited for him to ask about my ring preferences because of course I wanted a say in the ring I would wear the rest of my life. He didn’t. Then we planned a trip together and I had a feeling he might propose. So 1-2 months before I would bring up marriage more often and told him if he wanted to go ring shopping or get my size I’d be down. He brushed it off because I found out later he had already bought it.

I don’t hate the ring, it’s pretty nice overall. But I do hate the setting. It’s so damn tall for no reason. The diamond isn’t huge, and I’m fine with that, but it’s sitting on an unnecessarily large upside down A looking setting with a cathedral something or another. I think it’s silly and it gets in the way. He got it because my name starts with an A and was so excited to point it out 2 min after the proposal. I couldn’t care less, I’m not 12 and want my name on stuff – I don’t even like my name. 

Then he lost the ring. I saw it as an opportunity to change the setting, but wasn’t sure how to bring it up because he was so distraught about losing it, and he was so proud of himself for picking out the ring initially. Plus he was embarrassed and I was not allowed to tell a soul what happened, so if we couldn’t find it he was going to go back and get the EXACT same ring so no one would notice. 

It wasn’t looking good for recovery, and we had a deadline that if we didn’t find it by then we’d buy a new one. I waited, because I didn’t want to tell him if we did find it, then he would know I wasn’t satisfied with the ring I had. But without telling me, he bought another identical ring. So I still have that setting.” – Redditor iwontthrowawaymyring 

“Last night, I proposed to the love of my life. We’ve been together for a few years, and we’ve been through a lot, but we’ve always stuck together.

She kinda saw this proposal coming. I’m going on a deployment in March and we planned on getting court married soon as we’re engaged and having the big wedding after I get back. We’ve already made up our minds that we’re partners for life, so it was probably the lowest stakes proposal of all time.

What she definitely did NOT see coming was the rose gold diamond ring that was custom made with little waves in the gallery to symbolize the water ejecting from the case as I flicked it open, rolling through a crack in the pier, and plunging into the ocean. 

After a brief silence, and looking quite dead inside, I said ‘Will you marry me?’ And she said yes! 

Since then, she’s looked at my pictures of the ring and she loves it. It wasn’t outrageously expensive. To be honest, it cost a paycheck. I got in touch with the jeweler and since the saved the design digitally, they could easily replicate it and they’d give me a deal because they wouldn’t have to do the design work again.

We’re both traumatized, but happy knowing we’re really just in it for each other. That’s the silver lining I guess.” – Redditor gwpeterk 

As we’ve journeyed through these engagement tales of mishaps and misadventures, it’s evident that love is never without its bumps and twists. While these stories may not have had the idealized fairy tale beginnings, they serve as a testament to the resilience of love and the stories that truly make a relationship unique.

Remember, it’s not about the perfect moment, but the lifetime of memories you build together. So, whether you’re planning a proposal or just enjoying a good chuckle, always embrace the unexpected. After all, it’s these imperfect moments that make the most unforgettable stories. 

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Restoring Your Happy Ending

It’s essential to remember that no matter how wrong, damaged, or lost that precious engagement ring may have become, there’s always hope for a happy ending. 

At My Jewelry Repair, we understand that the sentimental value of an engagement ring often far exceeds its monetary worth. Our skilled team of experts is here to help, ready to restore that symbol of love and commitment to its original glory.

Whether it’s repairing a damaged ring, re-sizing it to fit perfectly, or even finding a lost stone, our dedicated professionals have the expertise to make it right. And for those who weren’t quite thrilled with their ring in the first place, fear not. Our team can work closely with you to reset the stone or replace it entirely, ensuring that your engagement ring is a true reflection of your style and preferences.

After all, every love story deserves a happy ending, and we’re here to help you create one, even in the face of those unforgettable engagement horror stories. 

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