Awkward Stories Of Marriage-Proposal Rejection

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Somewhere along the way, between the Disney princes and the viral videos, we’ve gotten some weird ideas about marriage proposals. For instance, there’s the notion that you should ask someone to marry you without having a pretty good idea how they’ll respond.

Uh, nope.

Proposals aren’t questions. They’re performances. At least, that’s what some sociologists tell us. If the scientists are right, no one should go down on bended knee until they know if their partner’s on board. That, folks, requires communication.

Forget mystery. Romance is all about understanding more.

Anyway, that message is garbled enough by our romance-performative culture that tons of people still get rejected when they ask someone to marry them. It’s awkward.

It’s also awkwardly entertaining. Check out these stories of rejected proposals, culled from the fine folks of Reddit. We edited them for grammar and readability. Oh, and if you’re considering popping the question any time soon, pay close attention.

We blame YouTube.

“It was our third date,” wrote OliviaAmazing. “He had taken me to a fairly average restaurant (which I can no longer return to), [and] had arranged a whole thing with the staff so there was music and flowers and candles and stuff.”  

“The place was really busy and everyone stopped to watch, and when I said no he started crying and had to be taken into the back by a couple of the servers. I was asked to leave and not come back, told I was horrible and cruel, etc. Lol.”

Still thinking about staging the perfect YouTube-ready proposal? Check out this story.

“We had been together for one month, and he proposed in a seaplane on my birthday,” wrote rilesroyce. “It was a surprise, and he was short $75 for the plane when we got there, so I had to spot him.”

“He brought out a ring and asked me to look into the camera and say what was happening ‘so we can replay this moment at our wedding.’ I told him to put the camera down and gave the ring back when we landed.”

The interesting thing about these stories is that no one ever says, “I regret saying no.”

“We’d been dating long distance for two months when he called me and laid out his entire life plan for ‘us,’” wrote bearsdiscoverfire. “We were to marry. Immediately.”

“I would graduate school, become pregnant a lot while using my (art) degree to support our kids and his suddenly desired career in full-time volunteer ministry work. Never mind our religious differences and my already-stated intention to remain childless.”

“He didn’t propose. ‘Propose’ implies asking. He just stated it as fact and was honestly surprised when I objected.”

Man placing engagement ring on partner's finger
Gift Habeshaw on Unsplash

“None of this was in my life plan, at all, nor was it discussed between us prior. He broke up with me very shortly afterward, citing my supposed inability to be a ‘reasonable, rational person’ in light of my rejection of his unilateral propositions.”

“We were both in our early twenties. Bullet. Dodged.”

In fact, the moral of most of these stories is that the right “no” is a pretty positive force.

“He was already married, offered to get divorced for me, and asked me multiple times with a ring,” wrote JLesh13. “I have no idea why in the hell he kept asking. We were coworkers, and he saw me as a challenge, I think. So obviously, [I] said no every time.”

Sounds like the right call. Here’s another example.

“My ex contacted me via text a couple of days after Thanksgiving, asking me if we could get married and run away together,” wrote Ilunibi. “When I told him that was a little strange, he lost his mind accusing me of judging him.”

“And that is why I said no. That is also what made it incredibly awkward.”

And another. This one features the novelty of a proposal conducted over instant messaging.

“My ex asked me to marry him (we weren’t together at the time) at work through IM so he would have someone to write home to when he left for the military,” wrote solowyouwillpoop.

“I said no because that’s stupid, and he had been seeing his ex while seeing me. He left soon after, and we never spoke again.”

And now, a breath of fresh air for cringe-relief.

“I said no because we’re not ready,” wrote Sakirexa. “We’ve been long +distance for three years now, and although we love each other very much, he knows I won’t marry him until we’re both settled in together.”

“Still, he asks almost three times a week, and it’s become a bit of a laugh for us. He tries to sneak the question in without me noticing, and I add ridiculous conditions to my yes.”

“I’m sure that when we decide to get married, he’ll be too nervous to actually ask properly … “

“It’s not all bad in ‘no’ world.”

A little self-awareness goes a long way.

“I said no because I honestly was not prepared for such commitment, so early and that fast,” wrote a Reddit user with a now-deleted account. “We had been seeing each other for about a year. I was 22.”

“He was 24 and was always the super-romantic kind of guy. Don’t get me wrong, I love this, but he was always rushing things way too early and too soon.”

“Luckily, he didn’t plan a fancy proposal kind of thing. [He] just surprise-asked me at home, so I had to say no then. It didn’t take long for us to break up eventually.”

If you end up having to decline a marriage proposal, don’t feel too bad about it. That’s a pretty difficult situation they’re putting you in.

“We’d been dating for three years, having some trouble, and he wasn’t interested in making any changes to work things out,” wrote clayfeet604. “He basically broke up with me.”

“[It] turned out I was relieved, then [I] found out he was really just bluffing to ‘teach me a lesson.’ When he figured out that I was okay with breaking up, he proposed.”

“[That] really p***ed me off. I actually responded with, ‘I have a date this weekend.’ I guess that was a little harsh, but don’t propose out of desperation because you screwed up.”

Here’s another example of some well-placed vengeance.

“I dated my high school sweetheart through the first year of college,” wrote KitchenSwillForPigs. “All through our relationship, he went on and on about how he didn’t believe in marriage and would never get married. Whatever. We were teenagers.”

“We broke up at the end of freshman year, but we tried to stay ‘friends’ because I was too young to realize he was just trying to get me back.”

“He brings up marriage and says, ‘I would have married you, you know?’”

“I just said, ‘Okay.’”

“He gets irritated and says, ‘Well?’ expectantly.”

“I replied with, ‘Clearly, since I broke up with you, I would not have married you.’”

“It wasn’t until later that I realized [this], but I’m pretty sure he was asking in some crazy attempt to get back together. He [chased] me for another year before I exploded at him. Definitely awkward.”

If you feel like you’re too young for marriage, you are.

“I was dating a guy during the end of my senior year of high school,” wrote my_hero_zero. “I was 18, he was 19. He proposed after a few months of dating.”

“Looking back on it, I think he was afraid I was going to move away to go to college and meet/date other guys. Marriage would have been his way to keep me forever.”

“I said no, because I knew I was too young, and I didn’t think he was the kind of person you want to make a life with. We continued to date for a while. We eventually broke up because he was just too insecure.”

Person holding out opened ring box
Austin Pacheco on Unsplash

“He always talked about how I was going to break up with him eventually for someone better. I took some time off before I started college, but I did have several other boyfriends during college, and after. I wasn’t really interested in marriage when I was younger.”

“Now I’m 31, and was married last year. The guy who proposed at 19 is married to someone else with a few kids. I know he proposed to other girls, too. I think he was just the kind of person who desperately wanted to marry anyone, where I was more selective.”

Here’s why it’s a good idea to decline an early marriage proposal.

“My ex proposed to me prematurely,” wrote another Reddit user. “I did see a future with him, but we were only 18 months into our relationship. He was in a bind. He had an incredible career opportunity across the country, and they would fund a move for him and his spouse.”

“Without that funding, I could not make the move at that point. I thought about it for a few days, and decided that it wasn’t the right choice for me. He told me I was wrong and walked away.”

“I have no regrets at all. In retrospect, I think it would have been a disaster had I accepted. It’s been three years, [and] we keep in loose touch.”

“His career is thriving, and he’s engaged to a woman who seems a much better match. I ended up moving elsewhere to pursue my own dreams, and I’m so glad I did.”

You always know you made the right decision when you see the next gal make the wrong one.

“We started dating two weeks into college and dated all through college,” wrote tasha4life. “It was really, really rocky the last year or so. Because I didn’t have an identity outside of ‘dude’s girlfriend,’ I had trouble breaking it off.”

“So I got a second job, enrolled in 18 hours, and decided I would get a 4.0 [grade-point average]. This was all done so I wouldn’t see him as much. The fighting decreased because I was too busy with all that to sweat the small stuff.”

“Well, we stopped fighting because I didn’t give a s*** anymore. He believed that it was a good sign and popped the question on the way home from his parents’ house in Chicago. On the plane.”

“Worst flight ever. It was a good decision, because it turned out he already had someone lined up, and they were dating within a couple of weeks or so. He got her pregnant I think three months after we broke up.”

“Poor thing. I remember that she used to call me about their relationship problems, while she was pregnant with his child, because I knew him better than she did.”

“It always struck me as insane that she was carrying his child, but also knew that she didn’t know him well enough to know when he was lying. Who does that?”

“She was beautiful too. Just a wee bit dumb … “

Youth is wasted on the young.

“I had someone (a friend I’d never dated) propose to me after high school,” wrote Veblenette. “I kind of laughed it off at first—where I live, people don’t get married that young.”

“But he was devastated, and he kept calling me to ask if I’d changed my mind. I told him no, and I asked him to move on with his life, but he kept telling me he ‘wouldn’t take no for an answer.’”

“Unfortunately, I had to get a restraining order against him. We haven’t spoken since. I still feel bad about it.”

Well, Veblenette certainly shouldn’t feel bad about that. If you’re looking for someone who should feel bad, how about the guy in this next story?

“We were 19,” wrote itgoeslikeDIS. “He proposed with a cubic zirconia ring and pretended to impress me (and all of our friends) by stating it was real.”

“In general, he was a chronic liar and cheater. Very insecure and seemed to be the type who wanted to ‘trap’ someone into marriage. I was much more insecure and passive then.”

“He got married two months ago. Thank God I said no.”

Don’t get the family in on the proposal unless you’re sure.

“Not me, but my aunt,” wrote Anne_Anonymous. “She had been dating this guy that the whole family was totally enamoured with (well-spoken, ambitious, outdoorsy, and genuinely kind) for about three years.”

“So Christmas comes along, and the whole family is in on this planned proposal (when she would inevitably break to take the dogs out for a walk, he’d accompany her and propose at their favourite park).”

“So sure enough she heads out, he eagerly goes with her, and we’re all celebrating inside the house because finally (again, this guy was awesome, and they were the world’s best couple). And we knew they’d been talking about marriage, so surely this would be a yes, right?”

“Wrong. They come back like an hour later (we started to suspect something was a bit off before then) and they’re not talking. Guy looks like he’s been punched in the stomach [and] is trying not to tear up.”

“[The] most awkward Christmas dinner ever ensues (recall: the whole family knew this was happening. And he had to sit through it, dejected).”

“Apparently my aunt felt that even though she wanted to be married (and had expressed so recently to him), she didn’t want to get married after all because people ‘would start pestering them about kids.’ I still don’t know how they got through that one.”

“Anyways, long story short, he proposed to her twice more over the course of the next seven years (family wasn’t in on these, and she had other excuses), before essentially telling her that if she ever wanted to get married it was her turn to propose!”

“A few years ago, they went to the coast for a holiday, and apparently she did just that. They eloped and were married on the beach, and there was many a sigh of relief when we all got the news. He looked so giddy in all of their photos. It was both ridiculous and adorable.”

Reminder: The Kwisatz Haderach of Dune fame is fiction.

“Not me, but my mom,” wrote possiblymaybejess. “My mom’s dad is a pretty successful businessman. My mom was working in some entry-level job in the same industry as my grandpa. The son of the owner of the company my mom worked for was a friend of hers.”

“He asks her to hang out one night, not a date or anything (she had been dating my dad for years at the time), and ends up proposing to her because his dad was a successful businessman, and her dad was a successful businessman, so obviously they should get married.”

“The words ‘good breeding’ were thrown around. Future children were brought up. Obviously, she said no.”

“TL;DR: Guy proposes to my mom to genetically engineer super-business babies.”

Saying “no” is difficult, but sometimes “yes” isn’t an option.

If you’ve already broken up with someone, you probably shouldn’t marry them. Probably.

“We were 19 and in a crazy on/off relationship,” wrote ButtercupCooks. “At the time of the proposal, we were off and in my head we were off for good. He came to my house and begged for me to come back, including a tear-filled proposal. I said no, got out of his truck, and went back inside. A month later, he told me he was going to be a dad. He knocked someone up around the time he wanted me back.”

In other cases, the proposal itself isn’t really serious—it’s just a (bad) way to stop a relationship from collapsing in on itself.

“It was simply a ridiculous suggestion,” wrote Cerealcomma. “We had been on and off—he hadn’t been speaking to me for months until about a week before the proposal—and we hadn’t discussed even dating again, and suddenly he was on one knee with an actual diamond ring.”

That’s a bold proposal if we’ve ever heard of one, and in this case, it didn’t work out. Neither did this next one.

“My ex asked me after we had broken up,” wrote Spin_me_right_round2. “He thought if he asked me to marry him, I’d realize he was ‘mature’ and I’d come back to him. I said no and told him to get out of my house.”

Here’s a unique one: Don’t propose at McDonald’s, unless your Big Mac is really, really good.

“A couple years ago, every week I’d go to this specific McDonald’s with my friends after a night [out], and it would always be the same girl taking my order,” wrote Faaaabulous. “Every time I finished my order and she asked, ‘Would that be all?’ I’d answer with, ‘And your hand in marriage!'”

“I did that for about a year. A few years later, I meet this girl through a mutual friend. Pretty girl. Cold at first, but we hang out a few more times and start to get along really well, so one day I ask her out. She asks me, ‘What, not asking for my hand in marriage anymore?’ I thought she looked familiar…”

Sadly, they didn’t end up married, although Faaaabulous still goes to McDonald’s (okay, we’re reaching for happy endings at this point). On a semi-related note, don’t propose through social media…even if you think you’ve got a pretty creative method.

“[He] showed up unannounced, months after our breakup when I had a new boyfriend,” wrote a Reddit user whose account has since been deleted.

He told her to check her social media, where she had a new friend request: a fellow named Will U. Marryme.

Light-up letter sign reading
Gift Habeshaw on Unsplash

“He looks at me. My face is red, and I’m shaking my head no. He leaves and drives home. Home is five hours away in a blizzard. Sigh…he tried. We’re still friends, somehow. Our lifestyles just didn’t sync up.”

Some of these stories have legitimately happy endings.

That doesn’t mean that they’re not a little awkward.

“I once said ‘not yet,’ because we were 18,” wrote rqk811. “That was why. We were kids. He was my first boyfriend, my first kiss… you have to be pretty sure [or dumb] to say yes to that…but…I said yes shortly after, and we’re 31 now and happily married.”

This next story is similar, but even sweeter.

“I said no when I was proposed to,” wrote LadyBlast. “My boyfriend (at the time) and I had a rocky relationship. We had been friends for a while but never got together because we were always dating other people. When we were both single, we clicked. Our relationship was rocky, because he was fresh out of [a] relationship and couldn’t decide if he should be with me or the ex.”

“The first time we kissed, I knew it was special. After a long, rocky period things were really great. We were happy. Then he started to change. He was distant, short, and didn’t seem to care about our relationship. I wasn’t going to put up with that, so I ended things. I was completely heartbroken.”

We swear this is going to be heartwarming. Stick with it.

“A week after our break up, I was standing in line at the bus stop after getting off of work. I had my headphones in when I felt someone put their hand on my shoulder. I thought it was someone trying to steal my purse. When I turned around, there was my ex. He asked to talk to me and pulled me aside. I was super mad and surprised to see him since he lived over an hour away.”

“He immediately got down on one knee. To say I was shocked would be an understatement. When he asked me to marry him, I was speechless. Some random guy at the bus stop was standing two feet away from us taking pictures on his phone and saying, ‘Say yes! Say yes!’ I finally said ‘Hell no!’ and walked away. I was furious at him for being awful and ruining our relationship.”

“By that time I had missed my bus, so my ex had to give me a ride home. It turns out, his reasoning for being distant was because he decided to join the military and couldn’t bear putting me through that and thought it wasn’t fair. Stupidest thing I had ever heard. That was over four years ago. Even though I said no to him, my husband is sitting next to me and things couldn’t be better.”

That’s right, she married the guy who joined the military. “I told [him] it was stupid of him to not let me decide if I wanted that life. I never actually said yes to see proposal though,” she clarified in another comment.

One Reddit user managed to turn down two separate proposals.

Some people have all the luck.

“The first time, it was my high school sweetheart,” wrote one Reddit user. “I said I didn’t want to get married or have kids. I said I was just looking for some fun. But he proposed with 13 roses, candles, and a beautiful emerald ring (I don’t like diamonds). I said no. We broke up. For a while, we didn’t talk, but ended up friends.”

“The second time was a guy I was seeing who was five years younger and a little weird. You know—dark and serious goth boy. I told him I did not want to get married or have kids.”

“But one day he just turns up at my house with this beautiful emerald ring. I said no. We broke up. We’re friends later for a while, then he ended up committed [to a mental health facility].”

“Finally, we come to the man who did not propose. No ring. Nothing at all. We were just out under a million stars in the desert and he said, ‘If we join forces, we’ll be more powerful together than we could ever be alone.’ I agreed. We got married. No rings, no ceremony. Just a quiet signing of papers at a registry office. We’re still together and happy.”

“Some people, if they are emotionally damaged, have trouble with the traditional stuff—diamonds and big proposals and all that. And it took until I was 32 for someone to speak to me in a way I could handle, but at least it happened.”

Finally, a story that tells it like it is.

“I said no because you don’t get engaged to convince yourselves you have a stable relationship that will make it for the long haul,” wrote torchie. “You get engaged because you’re already convinced you will. A ring is not a magical relationship Band-Aid.”

We couldn’t have said it better ourselves. If you are planning on proposing, here’s some great advice.

“I own a company that deals with various precious gems and metals,” wrote omni_wisdumb. “It’s really annoying that people don’t understand this simple concept. The proposal is the surprise, not the question of will she marry you. It boggles my mind how many people don’t understand this. You two are getting married, [which] means you both need to have talked about it. It’s not a surprise like getting someone a puppy—which [also] is a terrible idea if you haven’t talked to the person about if they’d like the responsibility of being a dog owner.”

That’s some bonus advice: Don’t get people dogs as gifts. Moving on.

“Honestly, if you propose, and your [significant other] says no, it’s a good thing, because you’re clearly not ready to be married as you lack the very foundation…communication!” they continued. “So, to all you women/men who’ve said no to guys/ladies that asked you without talking about it, even if you’ve been dating for 50 years, don’t feel bad.”

If you’re considering a proposal, talk it out with your partner. Consider going ring shopping with them. The surprise should come from the moment and method of the proposal, not the fact that the proposal is happening in the first place. With a bit of communication, you can avoid ending up in someone else’s proposal rejection story—and you won’t have nearly as much apprehension when you finally decide to pop the question.

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