There are some marriage proposals that just melt our collective hearts. Then, there are the others… The ones that make us want to crawl into a hole on behalf of the poor soul who dismally attempted to seal the deal.
Maybe bad planning is to blame, or possibly nerves. It might even be the universe stepping in with a resounding “Hell no!” Whatever the reason, many a man (and woman) have put their foot in it while meaning to put a ring on it. From the one who felt it appropriate to pop the question at someone else’s wedding to the dude who decided a funeral was the best moment, people have been sharing the proposal horrors they’ve had the displeasure of witnessing or experiencing.
Bored Panda has rounded up a bizarre list of stories from across the web for you to scroll through instead of attending that other important engagement you’re supposed to be at. May they serve as proof that while love might be blind, timing and judgement really shouldn’t be! We also have some tips for those of you who are planning to pop the question. You’ll find those between the images.
#1
My cousin proposed to his girlfriend at a public event on stage (they were performers) and got rejected. Then in private she told him yes but she “couldn’t accept his proposal in public”.
Anyway, they filed for divorce a month into being married.
Image source: lixroe, Freepik (not the actual photo)
Engagement season is upon us. It’s that time of year when people get all gooey and decide it’s time to commit for life. “Generally, engagement season takes place from Thanksgiving to Valentine’s Day, with Christmas proposals being a popular option for many couples,” explains wedding planning site, The Knot.
The Knot’s 2025 Real Weddings Study found that about 47% of couples get engaged between November and February. The site’s experts believe that people pick this time of year because it coincides with the holiday season… a period often spent with family and friends. What better way to celebrate?
#2
My friend and her boyfriend were watching tv one night. He tossed a ring to her and said “here you should wear this”. He later got mad that she had never said yes to his proposal and never wore the ring.
Like bruh, what proposal?
Image source: sniffasaurus, Freepik (not the actual photo)
Of course, not all proposals go according to plan. And if you want yours to fly instead of flop, experts say planning – and timing – are key. Most importantly, you and your partner should be on the same page to avoid an embarrassing “no” in response to your big question. But also to avoid your marriage ending in divorce in the future…
“It’s important to have conversations throughout your pre-engaged relationship about a myriad of topics, from having kids to living together,” warns The Knot.
The site’s “Jewelry & Engagement Study” found that prior to getting engaged, 51% of couples owned a pet together, 69% of couples lived together, 78% talked about political affiliations, and 87% spoke about the possibility of having children together in the future. But the most important topic was finances. Eighty-nine percent of couples polled said they discussed how to manage their money before getting engaged.
#3
When my boyfriend proposed to me, he accidentally knocked the ring off the bridge we were standing on and into the river below. It was the most dramatic and terrifying proposal ever, but also the most memorable.
Image source: Makeup_Maniac, rawpixel.com/Freepik (not the actual photo)
When it came to the issue of whether or not to get married, more than half of couples surveyed said they started talking about a possible engagement more than a year before the actual proposal. Only 2% said they never discussed it at all.
It’s a crucial conversation, warns The Knot. “Not only does this reassure you that you’re proposing to someone who wants to be married, but it also helps you build a foundation for your future wedding planning experience,” explains the site, adding that you should really listen to your partner’s thoughts on the topic before going out and buying a ring.
#4
When my wife was in college her parents were strongly encouraging her to marry this guy that they just loved for some reason. He was a few years older and in the Air Force stationed across the country from where she lived.
They helped him secretly arrange for the three of them to meet her in the airport as she deboarded a flight. She had been somewhere, don’t recall where, and he had gotten leave and arrived in town a couple days earlier unbeknownst to her.
As she comes down the jetway, there he is, dressed as a clown. Like full on circus clown, big shoes, face make up, hat, everything, holding a balloon with a ring tied to it. They had been dating but mostly long distance at this point and she was only 20 years old. He was like 25. But as mentioned, her parents loved this guy. So, there she is, with a clown on one knee, and no, she’s not into clowns. There was no clown history in their story. There stand her parents, all excited. She actually accepted.
Later I would ask why and she says it was more of being in shock and everyone staring and she didn’t know what to do. Needless to say, there was no marriage. She broke off the engagement about a month later. I’ve seen the pics and they are disturbing to say the least.
Image source: Justbeingme_92, EyeEm/Freepik (not the actual photo)
#5
Oooh ooh my friend told me how her first husband proposed: they were in his home country for Christmas and first, he left her alone in his empty house with no food and electricity all day and most of the night. He was out partying with his friends and she had just flown in. When she was upset the next day about being alone and hungry for hours, he told her that she *could have gone to the neighbor’s house and asked for food*… she didn’t speak the language and had never been to the country before. She was upset, so she called the airline to change her tickets to leave the next day. He threw an engagement ring at her and told her that she had ruined his Christmas and “here was her freaking ring”.
They did marry but ended up divorcing a few years later.
Image source: anon, Freepik (not the actual photo)
On the subject of rings, a surprising 77% of “proposees” polled said they were involved in selecting or purchasing their engagement ring in some way. Eight-in-ten proposers revealed that their significant other dropped hints about the type of ring they wanted.
“Shopping for the engagement ring together isn’t unheard of either, with 29% of couples saying that they intentionally looked at designs together before the proposal,” reports The Knot. The site’s experts suggest that you ask your partner directly if they want to be involved in shopping for the ring.
#6
I used to work at a pawn shop. A customer bought a ring from me and immediately proposed to his girlfriend. She said yes and we all congratulated them and stuff, but man. Least romantic place I can think of.
Image source: ClassyBidoof, Freepik (not the actual photo)
If you’re pinching pennies, you might be relieved to know that the average cost of engagement rings has gone down over the past few years. But that doesn’t mean they come cheap. The Knot’s “Jewelry & Engagement Study” found the average cost of an engagement ring is now $5,200. It was $6,000 in 2021.
Experts suggest setting a realistic engagement ring budget before you start shopping so you don’t spend what you can’t afford. The survey revealed that 71% of proposers had a budget and 92% of proposers paid for the engagement ring on their own.
#7
My ex proposed to me while I was breaking up with him.
He had apparently bought the ring and showed my dad months before, and my dad told him he was an idiot and I would say no.
Image source: vampyreprincess, zinkevych/Freepik (not the actual photo)
#8
Less than an hour after giving birth, as we get to settle and bond with our baby, my 3rd, his second, having been in a relationship roughly 5 years at this point: “I’m taking paternity leave, so I can actually be there this time, but work wants a copy of our marriage license to approve it.”
I’m half loopy and in that brand new baby afterglow, so I laugh and tell him that we can get the license but I still need a real proposal.
Never got that real proposal. But he got to bond, the kids are insured, and we’re still being pains in each other’s bums 9 years on, so there’s that.
Image source: Certain_Accident3382, nataliaderiabina/Freepik (not the actual photo)
If some of the horror stories in this listicle have taught us anything, it’s that planning is crucial. “Think about what your partner loves and what their dream proposal would be,” suggests The Knot. “The key to pulling off an epic proposal is to make it as unique and personal to your partner as possible.”
For example, if your SO loves watching movies and spending time outdoors, you could consider setting up a projector screen outside with blankets, pillows, and their favorite foods. Play their favorite movie, then put it on pause or wait ’til the credits roll before popping the question.
#9
Boyfriend of 4 months came by where I was working to visit, casual conversation. He said in passing, how do you feel about getting married?
I replied, I don’t ever want to get married again.
He said, I thought that’s what you’d say.
He looked crushed and miserable and left in a hurry.
It took me a week to figure out that was supposed to be a marriage proposal. I never saw him again.
Image source: Any_Assumption_2023, DC Studio/ Freepik (not the actual photo)
Don’t wing it, warns The Knot. Figure out long in advance what you’re going to say during the proposal. There’s the tried-and-tested, traditional route: “Will you marry me?” at the end of a heartwarming speech. Eighty-seven percent of proposers polled said they did this… but you can do or say what you want – as long as it’s special.
“No matter what you decide, make sure you speak from the heart and practice your speech before the big day,” suggests the site. “By rehearsing ahead of time, you’ll feel less nervous during the proposal. But don’t feel worried about stumbling over your words—it’s an emotional moment full of excitement and jitters, it happens.”
#10
Guy held big party for girlfriend’s birthday, got up to make toast and proposal, girlfriend’s five year old yelled out ‘No, don’t marry him’. She accepted, but they never got married.
Image source: fourlegsfaster, yanalya/Freepik (not the actual photo)
#11
I interupted my bosses proposal to tell him somebody ran out of the store with all the sopranos box sets 😭.
Image source: Whitealroker1, seventyfour/Freepik (not the actual photo)
While the one doing the proposing has the biggest task, that doesn’t mean the other partner shouldn’t also prepare. If you’ve been talking about getting engaged, and you have a feeling it’ll happen soon, start thinking about how you’ll respond when it does. Experts suggest something more than just “yes.” That’s provided, of course, that you don’t say “no.”
“Think of some sentimental things to say to your partner after the big question,” notes The Knot’s site. “You don’t need to have anything memorized or practice a speech ahead of time, but it would be a sweet gesture to say how you feel about your fiancé and how excited you are about your future together.”
#12
My ex proposed to me with a ring, which ended up needing to be resized so when it was ready, he asked me to go pick it up and as it turns out- pay for it. I was 27 at the time and just had a pit in my stomach like ‘this ain’t it.’ There has to be more to love than this. And there was.
Image source: anon, Freepik (not the actual photo)
Don’t get caught off-guard with chipped nails or dry hands. Prepare for engagement season and ring photos by doing some double-duty moisturizing, advise the experts. “Slather up your hands every night before bed with your favorite hand lotion (with gloves to lock in the moisture, if you so choose) to make sure they look perfect for those professional photos and Instagram selfies.”
#13
My dad took my mom to the mall and when they passed a jewelery store he asked her if there was anything she wanted from there. She said no. He said, “you realize I’m trying to propose to you, right?” It did work though, because they’re still married nearly 35 years later. .
Image source: damnmess, Freepik (not the actual photo)
#14
My uncle shaved “will you marry me?” In his back hair.
Image source: Randy252, Freepik (not the actual photo)
Bear in mind that your ring might not fit perfectly the first time. But experts suggest that you don’t run to get it resized immediately – unless it seems way too big.
“Your fingers swell in the heat, so if you do decide to size down, it’ll be very snug during the hotter months (and you could risk it not fitting at all),” explains The Knot. “And in cold weather, your ring might be looser than normal. To combat this, you might have to adjust it to its proper position every time it swings around your finger.” Hopefully, once spring rolls around, it’ll fit perfectly.
#15
At someone else’s wedding/reception.
Image source: N-y-s-s-a, frimages (not the actual photo)
#16
My mum and stepdad have been together for about twenty years. They are both anti marriage and have never done it but they live together, own a house and are basically married every way but legally. I call him my stepdad because its easier.
Due to some family drama recently (specifically my stepbrother being a jerk towards my stepdad about money, long and sad story) they ended up having to look into the legality of certain things and realized that essentially if they wanted to be safe with their money they needed to be married, largely for tax reasons that I don’t know the ins and outs of.
My mum came home from work after looking into all of this and said “so unfortunately we need to get married.” My stepdad responded “for christ sake.”
They’re not having a ceremony or anything but I’m wearing a fancy hat to the town hall whether they like it or not. (They think I’m joking).
Image source: brokkenbricks, Frolopiaton Palm/Freepik (not the actual photo)
#17
Ex-bf said to me: You and I are having dinner with Will and Mary. How would we sit at the dinner table? I said, “Who’s Mary and Will? It’s hypothetical. Me and you and Mary and Will? Long story short, after too many failed attempts. I said Will, you, Mary, and me? Are you asking me to marry you? He said, “Well, I dont know what you think?” Yeah, no. Our issue was that he could never speak to me straight about anything. I’m not committing to this rubik’s cube.
Image source: Spare_Refrigerator59, prostock-studio/Freepik (not the actual photo)
#18
My wife and I were eating our bacon egg and cheese that I had fetched on a cold winter morning. Apparently I looked thoughtful and she asked me what I was thinking. I said, “Well. I was thinking how much I’d like to marry you.” She looked surprised and said, “Well . . . you have to ask me first.” I did. She said yes.
We got married three years later.
Image source: RecycleReMuse, pressfoto/Freepik (not the actual photo)
#19
Not strictly a proposal but when I was 19 I started seeing this person 18F through a mutual friend, we had a couple dates and she seemed nice.
On our third date, she asked when I was planning to propose, and if I thought she could be pregnant by the autumn (it was June at the time)
That was our third and last date and the last time I ever saw her 😅.
Image source: Nymphomanius, cookie_studio/Freepik (not the actual photo)
#20
One of my co-workers was proposed to during the ad break for Coronation Street (Uk soap opera): “Here, I got that for you”, handing her the ring without looking in her direction. She said yes.
Image source: noodlefishmonkey, yanalya (not the actual photo)
#21
As we are landing in Vegas, my now husband saw a billboard for a wedding chapel. Hey babe it’s only $19.95. How about it? Really loudly.
Image source: RubiesNotDiamonds, daxeefdd/Freepik (nott he actual photo)
#22
I hid the engagement ring for my second wife in a deluxe Hickory farms cheese assortment.
Image source: civildefense, azerbaijan_stockers/Freepik (not the actual photo)
#23
My sister-in-law’s sister, “Beth”. Beth had been living with her boyfriend and they had been together for 3 years, both mid to late 20s.
Marriage came up. Her boyfriend said he didn’t believe in that. So Beth called her parents and asked if she could move back home.
Within 48 hours, Beth had an enormous rock on her hand.
I mean – theyre still together, seem very happy and have 2 adorable kids. But it was definitely a rushed “here, I want to keep you.” He literally did walk in, put the ring on her finger and asked if she’d stay.
That is the worst. My husband did propose on a sweltering 95 degree day.. I was just wishing he’d shut up and put the ring on already, being outside was miserable. .
Image source: Jumpy_Presence_7029, syda_productions/Freepik (not the actual photo)
#24
Boyfriend at the time said mid intimacy “marry me?” I didn’t respond. Afterwards he said “you never answered me” -I said I thought he was joking and that is not the way to propose. We broke up not long after.
Image source: DrKavorka231, Freepik (not the actual photo)
#25
My MIL gave me her mother’s diamond engagement ring to give to my son when she died. He and his GF came to dinner and I took him back to the bedroom to give it to him. My son goes back out to the living room and shows it to his girlfriend. She says how pretty it is and he says, “Here, you can have it if you want”. She says,” Well God Joe, not like that”. She gave it back to him. LOL It’s been 8 years, they are still together but not married.
Image source: 7sisters3brothers, pixel-shot.com/Freepik (not the actual photo)
#26
My sister is introverted and has always been very private about her romantic life (she’s opened up to me about certain people if she’s feels a connection, but otherwise she’s very private).
Imagine my surprise when I get a text message from not only someone I’ve never met, but someone she’s never even brought up in conversation! He introduced himself and told me his plan of MARRYING my sister and some surprise proposal. I don’t know how he got my number, but he also messaged her friends, a close coworker of hers, our immediate family, and OUR ESTRANGED FATHER 😳. Yup, he texted our dad, whom we have not talked to for YEARS, to ask his blessing 😳.
They had only dated for maybe 3, 4 months? When my sister found out (via estranged dad contacting her, and thus ruining her day), she was LIVID! Our mother—who is also problematic—was pushing her to say yes (not to ACTUALLY get married, but just to KEEP THE RING 🫠). Fortunately my sister has a good head on her shoulders, gave an emphatic NO, and when this guy issued an ultimatum (they didn’t even live together—she owns her own house), she told him to kick rocks.
The guy was upset and decided that he was going to go and date someone loosely associated with her tight knit friend group (someone’s step cousin or something). Tries to make my sister jealous by magically showing up at get togethers (she was not jealous, and the new couple was not close enough to the group to really be invited). Turns out he hounded this girl to hang out with her step cousin more, just to insert himself into their group. It was obvious and awkward to everyone (except the poor step cousin). It all came to a head when the friend group was planning a vacation together. Dude basically invited himself, and then (long story short) left the friend group in the lurch when it came time to pay. He and step cousin were really toxic too—likely because he was using her to try and make my sister jealous. It turns out that the step cousin was trying to make SOMEONE ELSE jealous 🍿. My sister opted out of the vacation early bc of work (and she could see right through her ex boyfriend (?). Sister got all the tea from her friends, the group was able to go on a nice vacation without those two weirdos, and I got to hear all about it during FaceTime 🤣.
Image source: electricsugargiggles, Freepik (not the actual photo)
#27
She had a horse that she adored and took wonderful care of. He told one of the barn workers to call her one evening and tell her the horse had a laceration on its foot, and to come right away! So she, crying and worried as hell, grabs bandage material and zooms over to the barn, where he was waiting to surprise her with the ring and a photographer. So her engagement photos are of her with red eyes, no makeup, no bra, and an old college t-shirt on, with bandage material in the background.
Image source: Napervillian, Kireyonok_Yuliya/Freepik (not the actual photo)
#28
My proposal was awful. He waited until the last possible day (he was leaving on a long-term work related trip). He took me to dinner at a really fancy restaurant which had light dimmers at every table and he wouldn’t stop playing with it, he complained about an upset stomach. After dinner he took me out to the hotel patio and said, I was going to walk you out to the beach but I don’t feel like it. Here’s your ring, will you marry me someday? In the meantime, I can hear the ice falling in the ice maker at the bar behind us. I waited 4 years for that proposal and he blew it hugely. I was pissed about it for years (still have bad feelings about it) BUT, we’ve been married for 28 years so ultimately, it wasn’t a deal breaker.
Image source: donttouchmeah, Freepik (not the actual photo)
#29
It wasn’t actually that bad, but rather funny. Backstory, my mom had a huge phobia of insects touching her. So, my parents were at the beach, my mom was big into sun tanning. My dad placed the ring box on her stomach while she was tanning planning to then pop the question when she would gently open her eyes, but she thought it was a giant bug and almost launched it up into the air she jumped up so quick lmao.
Image source: xchakrumx, Freepik (not the actual photo)
#30
On my *second date* with a guy, he cried and told me his father wouldn’t accept our marriage because I was Jewish.
Not technically a proposal.
My sister’s first college bf proposed to her at our house on nye. We were all just hanging out at our parents house, no big party or anything. He pulled a ring out and my sister was completely horrified and said no.
They’d been dating for… months. They were a terrible couple. He came down to the basement and smoked pot with us after she rejected him, and we fell asleep.
The next morning my sister was so pissed she told my mom the entire story including narcing us out on the weed. Luckily, my mom took me aside and said “If you regularly go into the garage, then come back inside and eat all the snacks, you’re not being subtle. I already knew.”.
Image source: whereisbeezy, pressphoto (not the actual photo)
#31
My husband proposed in front of the fountains at the Bellagio. But he was so nervous he’d drop the ring while putting it on my finger, he actually “put a ring on it” in front of a maintenance closet in the hotel.
Somewhere I’d read that the first song you hear after your proposal is supposed to be “your song”….so we walked back up the aisle as a married couple to the Pink Panther theme :).
Image source: checkitbec
#32
Guys don’t propose at sports games please.
Image source: cum_curtains
#33
I was 22, she was 21, last year of undergrad. Dating for about a year. We were each making plans for after graduation. Over winter break, we were in her parent’s kitchen around midnight and she could tell I was kind of worried about something. She asked if everything was alright, and I just blurted out “you are going to marry me aren’t you?”
Pause.
“Yeah, I guess so”
31 years together so far.
Image source: OkInevitable1873
#34
My husband looked at me and said “I guess it wouldn’t be that bad to get married to you.” I said “wait, does that mean we are engaged?” Him, “yes”. And that was it. Honestly, it was the best I could expect as I knew he wasn’t into socially imposed grand gestures, so I didn’t mind. Marraige is going strong, just had our first kid and I regularly get foot rubs and breakfast in bed. That’s the real secret to a good marraige. .
Image source: Casswigirl11
#35
My husband proposed to me in his room. I honestly thought he was joking because it was so casual…
He swears he’s going to do a “do-over” for our vow renewal… 13 years and nada….
Image source: Bubbly-Example-8097
#36
Proposing by hiding the ring in food – because nothing says “forever” like nearly choking on your engagement ring.
Image source: Relevant-Bar3380
#37
Proposing without a ring at a wedding. The bride had to buy her own engagement ring because the groom never thought of getting her one. They’re still together.
Image source: LordyIHopeThereIsPie
#38
A friend of ours had a high maintenance girlfriend and proposed in a rather public place, dropped on his knee and offered the ring, had spent hundreds on roses that he’d sprinkled all over the house. She refused.
There is a midnight sled dog ride that a friend had hired and had paid the driver to stop in the middle of the frozen lake so that he could propose under the northern light sky. She refused. It was a very chilly and silent ride back to the vehicle.
Image source: AlbertaBikeSwapBIKES
#39
Guy in the military was dating another airman (female, yeah I know). She was pregnant. He says to her, at a Burger King on base no less, “we might as well get married, I mean you’re already pregnant, that way we can both get benefits”.
Image source: Adorable-Writing3617
#40
Heard a guy proposed to his girlfriend at a fast food drive-thru right after ordering a burger,
Deffo not the romantic moment she was hoping for…
Image source: oucbndfladlzd
#41
I actually don’t think it’s the worst, but it definitely is a good story.
The couple was walking down a deserted beach in central America on a romantic vacation. He said to his girlfriend “I have something I want to ask you.” Before he could get on one knee, she asked him “is it about your third testicle?” She then went on a 3-5 minute riff about his (imaginary) third testicle and why it doesn’t bother her and giving it cute pet names and etc.
Then he said “well, no. It’s not about my third testicle” and got on one knee and proposed.
She said yes.
Image source: Uglypants_Stupidface
#42
My parents don’t remember who asked who. They somehow had a conversation about the future and both came to the conclusion they were getting married and began planning a wedding. Most boring worst proposal- if it even happened.
Image source: justalittlelooksy
#43
Walmart parking lot.
After they loaded up their groceries, he asked if she wanted to take a little walk. She was bewildered and worried about the milk, so she agreed to a lap of their parking row. About halfway down the row, he nelt down without saying anything and showed her the ring (on the plus side, it was a really cool ring).
At one point, I think she asked for a redo proposal, and he knelt down randomly and said “Will you marry me” while they were packing Christmas decorations.
Image source: doodle_rooster
#44
I used to work at one of those restaurants where customers can throw peanut shells on the floor.
I saw multiple proposals there.
Image source: anon
#45
Either at Disney or at another wedding.
Image source: bmcgowan89
#46
My parents. As I am told, my dad said to my mom, “So what are you doing in a couple months?” That was his proposal. They were married for 54 years by the time my dad died, having had little to no memory of the past several years due to Lewy Body Dementia.
Image source: ohlalalavieenrose
#47
My best friend’s marriage proposal. Her (now ex) husband decided to take her to their first date spot to propose. Okay, cute. But where their first date happened, you have to wear specific shoes since they were hiking and climbing on rocks. His idea was to propose on these rocks. But because my friend obviously wasn’t aware of this plan, she didn’t have proper shoes on and he never hinted that maybe she should wear different shoes.
Instead of attempting to help her climb these rocks and reassure her that he could help her get up on one of the rocks, he immediately gave up and walked her over to a random bench. He gave his little speech that she cannot remember because it was very generic and had zero thought behind it, then asked her to marry him. Then immediately after saying yes, he criticized her reaction.
Image source: acidic_crocodile
#48
Probably not the worst, but I once dated a guy who bought me a silver ring for Christmas. Since we had been together for a couple of years, I just thought it was a nice gift, so I thanked him for the beautiful ring, put it on, and was happy. The next day he goes “oh btw, that’s an engagement ring”, so I took it off and gave it back. It was too early for me to say yes anyway, but I informed him that if he ever wanted to propose he needed to actually ask me and not try to sneak it in.
Guess who did the same thing the year after…..
Image source: angelsontheroof
#49
Guy asked a family friend if she wanted good health insurance. She wasn’t even dating him.
Image source: EdelwoodEverly
#50
Arrange a fancy date night with your girlfriend, including dinner at a posh restaurant. In the middle of the meal, fake a brain aneurysm. Bite into a concealed blood pack, collapse and fall onto the floor, the whole bit. A “doctor” or a “nurse” planted at an adjacent table rolls you onto your back, checks you, and says that you’re not breathing and you have no pulse. He or she rips open your shirt to apply a defibrillator… revealing “WILL YOU MARRY ME?” written on your chest in red body paint.
Pull out the ring, and say, “I can’t live without you, baby.”.
Image source: Thatimensfaa
#51
Mine might be the worst. Was a broke 19 year old, thought that if I can’t spend money on a good proposal I’d go with the element of surprise. Wake her up at 3 am and give a speech about how we were going to be together forever and propose. Her response
“ARE YOU KIDDING ME…”
married 14 years this October.
Image source: the_navillus
#52
Chucking the ring at them and saying “here, wear this”.
Image source: anon
#53
My mom told me that my cousin’s girlfriend got tired of waiting for him to propose (apparently he said he would but hadn’t gotten around to actually doing it) that she straight up bought a wedding dress and told him they were getting married. He said, “Ok.”
I believe they’ve been married for about 20 years now.
Image source: PorkrindsMcSnacky
#54
Write the proposal on a positive pregnancy test.
Image source: prajnadhyana
#55
I saw a video of a guy proposing to his girlfriend while she was driving, once. That’s pretty bad imo.
Image source: anon
#56
“oh yah” He rolls over in bed before the lights go out.
“will you marry me?” he said before falling asleep.
i think this is it.
Image source: anon
#57
Will you marry me?
[ ] YES [ ] NO.
Image source: TheExtraMayo
#58
For me personally the worst would be any grand gesture around people. I’d rather you ask during a cozy night on the couch. My ex and I just talked and knew we were going to do it. We picked up the ring together and were walking out of the store. He bent down on his knee at a bench , no one was paying attention. I’ll never forget how precious that was to me. I was at a large music festival last year and saw a guy propose to his girl quietly in the back of a crowd. No one seemed to notice that either but I saw it and started crying to myself at how beautiful it was. She was snuggling into him the whole rest the set.
Image source: anon
#59
Flash mob or at a sporting event where they’re on the jumbotron.
Image source: knaveben
#60
At her university graduation as a neurosurgeon, he (a janitor) grabbed her doctorate out of her hands, got down on one knee, put her on the spot…in front of her colleagues, professors and family. Oh yeah, he made the ring out of a piece of plumbing pipe. CRINGE.
Image source: creepyjake
#61
This is the story of how my parents got engaged.
Dad: Hey, you should move in with me.
Mom: No. Not until we’re married.
Dad: Okay. Fine. Lets get married.
Mom: Wat. Are you seriously asking me like this?
Dad: Yes. Why not. Marry me and then you can move in with me.
And then then they got married.
It did not go well.
Image source: biddily
#62
At the surprise wedding you threw them.
Image source: angelerulastiel
#63
Guy takes his girl on a helicopter tour, says nothing until after the ride, in front of the still loudly running helicopter, on a greasy tarmac. I’ve got more stories from my tour pilot days. Lots of proposals.
Image source: tamboril
#64
A guy I used to work with said since him and his paramour would always get the same Wendys meal on a certain day, he had them insert the ring in hers.
I forget the details, but he said she said it was so corny that he would have to try again.
Image source: Fritzkreig
#65
Probably mine 😂
I’m one of those “marriage is an archaic institution” types but it’s important to my husband to feel secure. He totally respected that it was an ideology thing and not a lack of commitment thing and never really brought it up. I decided his feelings were more important than my disregard for the system, so one day, pretty out of the blue, i said (something along the lines of) “do you want to get married? it’ll take like a week to get all the paperwork together, and i really don’t want to do the whole ceremony shenanigans, can I just ask my best friend to officiate our wedding next time she’s in town?”
He did still marry me about a month later though (the next time my best friend was in town) so it must not have been *that* bad. We invited our local friends out to dinner and had little signs on the table that said “surprise we’re married” and sent everyone else post cards. Our 5 year anniversary is a couple months away and we’re happy, so I didn’t ruin anything.
Image source: lestabbity
#66
I was sitting on the bed in a hotel room in Italy, and my boyfriend chucked a ring box at me and said “I suppose we should get married, then”.
I was already pregnant with his baby and did love the fool, so I wasn’t going to say no, but I did ask for a do-over with a bit more feeling. It’ll be 15 years in December.
Image source: spankybianky
#67
One of my fiance’s friends had been having health issues for about six months. She knew her fiancé had the ring but he didn’t think to propose to her at the time. She was driving herself nuts with when he was going to do it and stop asking about a proposal for about a month before it actually happened.
She had come back from a very difficult appointment and was having a breakdown on the floor of their office. Her now husband decided that this was the best time to give her the box that the ring was in and give it to her.
Idk if he actually said “will you marry me?” but part of me will always think he gave her the ring to shut her up.
Image source: Adventurous-Depth233
#68
My parents. Mom went to visit Dad and his next door neighbor asked “I don’t mean to pry, but what are you and (Dad’s name)? Like, are you dating, engaged, what?” And Mom said that was a good question, and asked Dad “Your neighbor wants to know if we’re dating or engaged or what.” He asked if she’d like to be, she said “engaged, you mean,” he said that was what he meant, and she said yes and they went to buy a ring.
Image source: eclectic-worlds
#69
I was in Costa Rica on a hike to a big waterfall through an animal conservation place. A guy also hiking asked if I could take a picture of him surprising his girlfriend with a proposal. He was so nervous.
We kept walking by small water features and then eventually a larger man made waterfall. He gave me the signal and walked her under this glorified fountain and proposed. It was sweet and all and she said yes.
A few more miles into the hike, we saw the real giant waterfall. It was awesome. The look on his face when he saw it was pure disappointment like he had really screwed up.
I pulled him aside and reminded him that she said yes and didn’t know his plan. He told her how sorry he was for screwing up. I hope it is now a funny story in their happy life.
Image source: oscarbutnotthegrouch
#70
I know of someone who proposed to his girlfriend while she was sitting on the couch, tired from working a 12 hour shift, shoving a Big Mac into her mouth. He just walked up, opened the ring box and held it at arm’s length to her, saying nothing. Apparently he told everyone he proposed to her in the park while on a picnic.
Image source: davidgrayPhotography
#71
A best friend and I used to propose to one another just to embarrass each other. The first time was pretty cute, it was at a botanical garden and there were lots of tourists around. But one of the other times was at a Taco Bell and I put the ring on a nacho fry when I offered it. The looks people gave were absolutely mortified.
Image source: tenehemia
#72
If it’s not a 100 percent sure thing I wouldn’t go trying to put it on the kiss cam at the big game.
Image source: ITeechYoKidsArt
#73
Friend of a friend proposed to his fiancée immediately after her grandmother’s funeral.
The logic was sweet, but deeply misguided: her family lived across the country, so it was one of the very few times her family would be all in one place. Additionally, he was planning to ask her at a romantic dinner the week before, but those plans fell through when her grandmother took a bad turn.
She was initially pissed, embarrassed and mortified, but said yes … but it’s been 5 years and no wedding in sight, so 🤷♂️ .
Image source: anon
#74
My friend dated a guy who was in basic training (for military) and cheated on her with several people while there. He was also sending the exact same messages and nudes to all of these women. Her parents had given him $$$ to pay off some of his debt before he went to basic.
When his girlfriend (my friend) found out and tried to dump him, he sent her several unhinged texts and proposed to her over text as a last resort. Obviously that didn’t change her mind.
Image source: boohoo_bear
#75
The worst one I ever witnessed was a dude who brought his girl to Fenway park, and proposed on the Jumbotron.
She said no and the entire park erupted in laughter. I didn’t feel bad for the guy.
Image source: Inourmadbuthearmeout
#76
My SIL told me about a couple who she knew that got engaged while on vacation. It was some sort of tropical destination where he would have had any number of good proposal opportunities.
They were in the living room area of their suite watching TV after a long day and he started picking at his toe. Apparently he had a something weird going on with a toenail and asked her to get him the clippers from the bathroom because he didn’t want to walk on it. She got up to get the clippers from the bathroom and he followed her and got down on one knee in the bathroom and proposed. She said yes. No backstory, no followup, that was just how he decided to propose.
Image source: Affectionate_Pea_811
#77
Nothing I’ve seen or heard in person, but every viral vid of some idiot proposing at a sporting event or show in front of tens of thousands of other people, only for the woman to say no or run away.
It’s extremely hard to muster any sympathy for these dolts. How do you even get to the stage of proposing marriage without first testing the waters with the person you plan to propose to?
Maybe find out if she’s actually interested in spending the rest of her life with you before making the proposal, let alone planning to make a huge spectacle out of it. On that note, don’t stop at finding out if she wants to get married first, best check that she’s cool with HEY EVERYONE! LOOK AT ME! spectacles before planning to use tens of thousands of other people as props for your little show.
Image source: Pixelated_Penguin808
#78
A friend of mine proposed to his girlfriend when he wasn’t even in the room. He had bought the ring and was waiting for the right moment to ask; they had planned a nice dinner date and a trip to a wine bar they were regulars at so he thought that would be a good time to pop the question. They had a few drinks at the wine bar, and because they were regulars, the bartender found an open bottle of wine that someone didn’t put the open date on, so they didn’t know how old it was, so they couldn’t sell it; he offered them the wine for free, so they got more drunk then they planned to. They ended up at another bar and then she wanted to smoke a joint, so they got high as well. My friend decided this wasn’t the best way to ask, so he decided to postpone the proposal. They went back to their apartment and went to bed.
He got up the next morning and went to his coat to take the ring out and rehide it from her…and the zipper on the pocket was open and the ring wasn’t in it. They had taken several Ubers the night before and it could be anywhere in the city by now; and the ring was an antique ring she saw in a shop that she liked, so it wasn’t like he could just go buy another one. He started frantically searching the apartment, hoping he dropped it at home and not in a bar on an Uber, she gets suspicious as he is not a morning person at all, and goes to get out of bed and finds the ring in the sheets. Apparently in his drunk state the night before, he had put it in his pajama pocket and planned to put it in his nightstand but passed out first.
She walks up to him searching the kitchen with the ring in her hand and says “are you looking for *this*?” He says “oh…yeah…so?…how bout it?”
She said yes and they’ve been married for 7 years now.
Image source: A911owner
#79
My arsehole cousin likes to tell everyone that her husband proposed to her on top of the Eiffel Tower. I know from a night when her arsehole husband got pissed that he proposed to her in one of those street toilets where you have to pop a pound in to use the facilities. Oh yes, a pound, not a euro – he proposed to her when they went over to Edinburgh (not the most romantic shithole in the world). The pair of skanks.
Image source: PureDeidBrilliant
#80
Saw a teenage boy propose to his girlfriend in a Walmart with a costume ring. She laughed awkwardly and said, “Haha, you’re so funny.”
And then the guy angry and said loudly, “You’re gonna say yes, right?! You better say yes!” I could see the girl quietly trying to diffuse the situation, but he just kept yelling at her. I didn’t hear what else she said, but suddenly the guy started shouting, “SHE SAID YES!! SHE SAID YES, EVERYBODY!”
And the crowd of people kind of turned to look and like two people awkwardly clapped, lol. That poor girl looked mortified. I felt so bad for her. I hope she gained the courage to ditch him. .
Image source: Moal
#81
“You need to figure it out. Are you going to marry me or not?” For context, this was the first time he had discussed marriage with her. And yes, this is exactly how he asked her. She said yes. And they have a horrible marriage. 🤦🏼♀️.
Image source: ElleWoods127
#82
I got asked in an airport garage. After he hadn’t shaved or brushed his teeth for a week.
Image source: Kitchen-Arachnid-494
#83
I had a classmate in college who congratulated me on my recent engagement when we came back from summer break. I told her how it went, she sighed and said “I got engaged too.” I congratulated her, but she stopped me and said “My fiancé didn’t ask in a light rain in a garden in Italy, he called me into the bathroom after he dropped a deuce.”
FYI, Both couples in this story are still married.
Image source: AllThatsFitToFlam
#84
It might just be a local thing, but when kids ask each other to prom they do something cute and creative to ask the other person to the dance.
My brother did this for his proposal. He made a big cardboard sign saying “will you marry me?” gathered his friends and cousins together and popped the question. Super cringe.
Marriage lasted 4 years.
Image source: binhex225
#85
Mine was not good.. we were just chilling watching a movie and eating some homemade Chinese food. She paused the movie to go to the restroom. I went and got the ring quickly cause suddenly my brain was like “NOW DO IT NOW”.
She came back after a while, obviously with an upset stomach but I asked anyways. She said yes, embarrassed that she just had diarrhea before getting proposed too. Not 5 minutes later it was my turn to spend an hour on the toilet praying to whatever god would hear me.
Double food poisoning proposal was not how either of us envisioned it going.
Image source: Favren
#86
My sister has had two awful proposals. The first was Christmas time and he went to hand her a box and she said “if it’s not a ring I don’t want it”. Which escalated into a huge fight and ended with him yelling at her to just go grab the other box from his coat, where the ring was.
The other was the pregnancy test popped up positive and he said “well I guess we have to get married”. She married him🙄.
Image source: littlescreechyowl
#87
My cousin’s ex fiancé proposed to her in the car while parked in a gas station parking lot. We literally had an intervention when she came back wearing a ring.
Image source: Radiant_Maize2315
#88
My friend’s story was pretty bad. They were sitting on the couch and she was scrolling through Facebook and said “oh look, so and so is Facebook official now” And he said “Speaking of Facebook official…” and pulled the ring out of his pocket and proposed.
Image source: Novel-Imagination94
#89
Have a tension rod with a small banner wrapped around it tucked into your pants. Go out to dinner at an upscale formal establishment. Call for a toast, stand up, unzip your pants, and when the rod expands, have the banner unfurl to reveal the message.
Proceed to urinate on the floor.
Image source: anon
#90
During a romantic submarine ride.
Image source: in-a-microbus
#91
My best friend swears he proposed by pretending to find a ring while eating out his gf and asking her who’s ring it was… he has never wavered from this story.
Image source: MikElectronica
#92
In public.
Image source: HolidayNothing171
#93
Text.
Image source: Salty-Entertainer-29
#94
Show her the ring then put both hands behind your back. Say pick a hand now….
Oops sorry wrong hand… No proposal this time…
Image source: anon
#95
Any of those cringe “I’m the main character” public proposals.
Image source: Jsmith0730
#96
Putting them in a full nelson until they submit.
Image source: MythsOfOpportunities
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