50 Men Who Gave The Absolute Worst Proposals In Human History 

50 Men Who Gave The Absolute Worst Proposals In Human History 

These stories from Ask Reddit are insanely cringey.

1. Before we were married my wife had a friend who had a boyfriend and they were both those types that are weirdly into weed. Look, I got no problem with weed. I’ve smoked a little myself in my day. But these were the “wear pot leaf themed clothing, get a pot leaf tattoo, have more money invested in weed paraphernalia than anything else” types.

They got engaged when he wrote “Will you marry me” on the inside of a rolling paper and asked her to roll him a blunt while we were at a bonfire. She said yes, then they smoked it together to celebrate.

2. My buddy’s girlfriend kept telling him that he couldn’t surprise her. After college, they were planning to move together to another town. About 6 months before graduation, he told her he wasn’t sure about the move or their relationship. She turned around to cry. He called her name, and when she turned back, he was on one knee. Did it to surprise her.

3. Worked in a restaurant in the early 90’s and a waitress told this story…

She was on a date with her boyfriend and they both got back to her place. He want to the bathroom and then she went in. While in there he calls to her “hey did you see what I left you?”

She said, “I’m not looking in there, you’re gross”.

She then opened the door to asked him what the hell?

He then said “you ruined the surprise, I taped your engagement ring to the underside of the seat cover”.

(Sad, but) true story.

4. Me and my sister went to watch twilight new moon when it first came out and when we walked into the theatre this guy and girl were up in front of the whole theatre giving a speech about how she was his lamb and he was a lion a la first twilight cringe Edward speech to Bella. He proposed, she said yes, and they then proceeded to sit down and watch that mess of a movie. I was shook and I still feel the cringe to this day. It wasn’t even a nice theatre lmao

5. My cousin’s marriage proposal was ruined because the person next to them at a booth (restaurant) told his gf that he saw my cousin writing the marriage question underneath the table cloth (she was supposed to lift it up and see it later on) when he was in the restroom.

6. I’m on good terms with one of my ex-girlfriends, so I got to hear this story of how her husband proposed to her:

They were sitting around their apartment one day and he asks her, “hey, can you get my phone from the bedroom?” Okay, she gets his phone for him. A minute passes. “Hey, can you get me a glass of water?” She gets him a glass of water. Another minute passes. “Hey, can you bring me that pair of socks on top of my dresser?”

She gets the socks. The ring is in the socks. He proposes. He actually thought he was being romantic. She thought it was weird as fuck.

Even weirder, she said yes, and they’ve been married for more than ten years.

7. My wife’s friend was proposed to by her boyfriend (at the time) at her grandmother’s grave. Her grandmother recently passed, and they were there to put flowers on it, and he proposed. On Christmas eve. I cringe every time I am forced to remember this happened.

8. Someone who I used to work with had the most uncomfortable proposal story, that to this day I can’t believe she told people. Apparently she asked her boyfriend (of 6 years) when he was proposing, in a casual way while they were driving. He said “you have to do something for me first” and gestured to his crotch. Andddd she blew him, and he told her to open the glovebox, and gave her the ring. That was it.

If I were her, I’d at least change the story to make it somewhat romantic/ palatable. Or keep it vague and say he proposed in the car. Either way, 10/10 trashiest proposal story I’ve ever heard.

9. My dad proposed while he and mom were watching TV at her parents’.

Not altogether too bad, but he didn’t turn it off. Waited for a commercial.

10. I was an emcee at a costume contest. I was told by the stage manager that a skit was performing as a entrant, and one cast member was proposing to another. The skit was some Zelda spoof. As it ended, “Link” said he had one more thing to say. He grabbed the hand of a cast member, got on one knee, and asked for her hand in marriage. Audience went “awww” but cut it short because, I suspect, they could see the woman’s face from their point of view.

“No. Just… NO!” she responded in frustration, and ran off stage crying.

The audience of about 1000 people was dead silent. Link got up, but was standing on his own cape and fell face down on the stage. His cast had already scattered backstage, and no one went to help him. He got back up, sheepishly chuckled, and limped offstage and ran past me.

Audience was still quiet. I had to get onstage and introduce the next participant and everyone pretended like nothing happened even though it was all we could think about. Normally, I made some stupid pun or joke about the previous act, but what could I say?? I still cringe so hard at this memory, I get a sinus headache just thinking about it.

Later, I found out it was one of those, “maybe I can save the relationship by proposing” blunders.

11. At an Army ball – Chaplain’s assistant proposes to his girlfriend in the middle of the dance floor to the song “If you like it then you shoulda put a ring on it.”

12. Apparently when a friend of mine and his girlfriend got engaged it was because they were arguing in a restaurant and he just said “DO YOU JUST WANT ME TO PROPOSE TO YOU?!”. She apparently took that as an actual proposal and talked about how cute it was to other people. She was a bridezilla during the whole planning stage, they DID get married, and then she admitted that she had cheated on him with an old college boyfriend and was moved out of their apartment before they even hit the 6 month mark. And people were shocked when his best friend said that he would not give them their blessing…sounds like dude was right not to.

13. My boyfriend tried to propose to me when I confronted him about his drinking. I guess he figured I’d be happy and forget everything.

I said no and he went to rehab.

14. Old roommate threw the engagement ring on the bed his girlfriend was laying on. She looked at him and, in short, told him to do better.

15. Facebook friend went on a cruise with her boyfriend to some nice islands somewhere (I forget). He proposed to her on the trip, on video.

But he did it during a busy mealtime on the cruise in the dining area rather than, you know, anywhere on the beautiful islands they were about to visit

16. I had a buddy who claims he ‘pretended to drown’ like 50ft out into the ocean, made his future ex-fiancé pull him all the way back and give him CPR. When he came to I think he proposed because he would never admit to having actually drowned.

17. My dad proposed to his gf of twenty years while she was throwing up sick from food poisoning.

18. When my mother was younger, she was riding in the convertible of a man she had been seeing briefly. At a red light, he pulled a ring box out of his jacket, tossed it across to her casually, and told her he’d marry her if she lost twenty pounds.

She didn’t marry him.

19. Writing it out in gasoline and lighting the gas on fire.

20. Ethan from H3H3 put the ring in a thing of baby wipes and asked his gf to get him a baby wipe while he was taking a shit.

21. A guy changed his Facebook relationship status from “in a relationship” to “engaged”. When his girlfriend called him to ask about it he responded: “well, what do you say?”


22. A friend of mine proposes to his partner while she was sat on the toilet, she was having a poo. Everyone slated him and his logic behind it was that in any situation with her can be romantic.

23. A buddy of mine was trying to be romantic by taking a walk on the beach and proposing in front of the ocean. Except it was in New Jersey. In September. She didn’t bring a jacket so she was just trying to “wrap this walking shit up” and get back to the car, and he kept angrily trying to slow her down and find the right moment to do the deed. Eventually he just said, “God [fiance’s name] I’m trying to propose to you here would you stop for a second!” And shoves the ring box at her.

She said yes. Fought all the way through the wedding. Still married. Bless their little hearts!

24. This story is from a friend I have in Cali. Her first marriage was to an abusive jerk-bait.

Apparently, he took her to Mervyn’s while they were closing because, “big discounts.” He bought her a ring that was originally $1,200 marked down to $400. Not that money is everything. Hell, I made my wife’s ring. But it’s the principal. He spent hundreds of thousands of dollars on bullshit like a LOTR sword that sat in storage or a $500 book that was useless. Anyway

He buys her this ring and she’s happy. She’s waiting for the proposal. But the ring just sits in the box on the kitchen counter for two weeks. She finally asks him when he’s gonna propose, and he says, “I already did. I was waiting for you to put the ring on.”

After some persuasion, he rolls his eyes, gets up, grabs the box, gets down on one knee while she’s sitting on the couch and asks her to marry him.

She shoulda run.

25. My college boyfriend and I had been together barely two months, he was 19 and I was 21. We got invited to a booze cruise. Half way through the booze cruise out in the middle of the ocean with frat boys yelling chug, sorority sisters holding each other’s hair back to barf and standing on the roof of this old tattered mesh carpeting I began to admire fireworks in the distance and turn to tell him how much I love fireworks to find him on one knee. I was extremely confused and thought maybe he had gotten sick too. He then grabbed my hand and asked me to marry him.

26. My friend proposed to his (now wife) through a WhatsApp message saying “I guess we should get married” because they were in an international relationship and had only met in person like 3-4 times before that.

27. My husband proposed in the car on the way to the grocery store. After we got home, we ordered rings online.

28. My coworker (corporate employee, very professional and uppity) was proposed to in the parking lot of a movie theater after watching the Dumb & Dumber sequel…. and she said yes….

29. I knew a guy that proposed to his girlfriend in the bathroom of a gas station. They did not get married.

30. My cousin proposed in Burger King with an onion ring. She said yes.

31. Some high school friends of mine went to Olive Garden where the guy was gonna propose, but he has really bad social anxiety and asked her in the car after they ate. She didn’t give him an answer for a few days. I can’t imagine that drive home.

32. In-laws were in a gas station at around 1 am. He asked her for a quarter. He then bought a 25 cent plastic ring from a candy dispenser. He didn’t even get down on one knee. He just asked if she would marry him, with a plastic ring she paid for.

33. At my masters degree graduation ceremony, there was an airplane pulling a banner that read, “Will you marry me Susan?” (I can’t remember the exact name). Every speaker at the ceremony closed their speech with, “So Susan, what’s your answer?” No one knew who she was, but it must have been excruciating for her. Eventually a woman held up a sign that said “Maybe”. We all knew that she really meant “No”.

34. My sister’s friend was proposed to in the bathroom while she was getting ready to go work the night shift.

35. I heard a story on the internet once in which a guy borrowed a ring from a store owner and proposed to his girlfriend. She said yes, then he immediately gave the ring back to the store owner. She was pissed after that.

36. My wife told me about how her first husband proposed. They had some friends that took a trip to Vegas and he proposed during the fountain show at The Bellagio, so her ex did the same thing.

37. Sent a text message that said, “Marry me.” I replied back, “Okay.”

38. Dad proposed over the phone and stated they “might as well.”

39. I was attending my brothers best friends 20th birthday party. He got wasted, blew out his candle, and then proceeded to propose to his girlfriend in front of everyone at the party. He gave a sloppy slurred speech about how they’ve only been together for 5 months, “but it’s okay because it was kind of magical”. It took a whole 4 minutes of him saying “please” and “I love you baby” for her to say yes, the guy didn’t even have a ring. Everyone was speechless like we literally fucking clapped, no cheering and no congratulating. I will never forget the look on her face, I have never seen a person force a smile that like.

The last time I saw them together was when I was driving home 3 months later. She was walking really fast, without a jacket, in the freezing rain. He was in his car driving alongside her, apparently trying to get her to get in. Needless to say, there was no wedding.

40. My own… My Ex-husband pulled over and proposed in a Motel 6 parking lot with my hysterically crying 1 month old son in the back seat…

41. Start of a tour around Thailand. The guy decides to propose on the tour bus on the first night with a bunch of strangers.. she didn’t even look at him and led to an awkward following 7 days. Don’t know why he didn’t propose on the nice beach…

42. So this one happened in my freshman year of high school. One of the girls in my year (about 15 at the time) was dating a guy who was about 22 if I remember correctly. He proposed to her in a Pizza Hut and the ring ended up turning her finger green. She ended up graduating high school early and getting married at 17, her parents had to legally sign off on it I think. I’m fairly positive they’re still together now, so I don’t think it bothered her at all. I just remember thinking at 15 that Pizza Hut had to be one of the least romantic places I could imagine for a proposal.

43. The girl got impatient. Finally she decides to take the initiative. She left a card on the dining room table that says “Will you marry me?”

He sat down, looked at it, looked at her, looked at it, opened it, read it, set it down, and started eating. She is obviously about to jump out of her skin. Finally she says “So what do you think?”

He says “Where the hell is my ring?”

They’ve been married for 16 years and have two adorable kids.

44. My ex lied that he was going to get deported. Gave me a ring that “was his grandmother’s” Which was missing a bunch of stones and not resized.

45. My sister’s husband proposed to her by sitting next to her, taking out the ring, sliding it over to her, and saying “here”.

She’s really big on romantic proposals. She would have loved the whole restaurant reservation, tapping the glass, proposal speech, and getting on one knee scene. So it kind of crushed her because it seemed like he didnt make an effort. Not sure what his perspective is.

46. My housemate comes from a *very* religious community. Like, they have their own shops, restaurants, their own college. They used to have their own high school but it got shut down for some reason.

Anyway, the friend’s fiancé proposed to her 20+ times over the course of several months. The church encouraged him to keep on harassing her, and the church shamed her into giving in. They told her that it was her “duty” as a woman to get married and have children, and that she was getting too old anyway (she’s 27!).

Eventually the friend broke down and agreed to marry him. All of her female friends, her sister and her mother are all trying to convince her not to go through with it, but she’s made up her mind.

I think they’re getting married in April.

47. A friend of my sister had specifically told her boyfriend she hated public proposals and didn’t want a bunch of people there, so what does he do but gather their entire extended family to do it. Ugh.

48. One day he drives her to a surprise location for a date. He takes her to this random house in the suburbs with a dog tied up in the front lawn. He then proceeds to propose and explain how her bought the house of their dreams, dog included, and how they could raise their children here. The woman (my friend) was so flabbergasted that all she said was something like “wtf, you bought a house and a dog without even telling me?” He thought he was making this grand romantic gesture, but she was super annoyed that he had apparently arranged their whole lives without even asking for her input. Needless to say she said no. Last I heard he lived in the house for a bit and then sold it for a loss. No mention of the dog, but I’m hoping it wound up with a good family.

49. I remember seeing a Youtube video about a guy who proposed on some light-hearted late night game show or something. Everyone was getting into the fun, happy, late-night vibe except the woman, who had a look of pure horror on her face. Eventually she whispers “Can we…..can we talk about this later? Please?”

There’s this awkward silent pause that goes on and on, while the couple both look like they want the ground to open up and swallow them whole. Then the show starts playing some cheesy upbeat “Let’s go to the ad break!” music.

The juxtaposition between the humiliated couple and the cheesy party backing music, just made it hilariously tragic.

50. My parents. They were in the produce section of a grocery store when my dad says “all our friends are getting married we should too”. My mom thinking he was joking just said yea and moved on with shopping. A couple days later she got to thinking about it and with the serious way he said it had her confused. She goes to him and asks if it was a serious question or if he really was just kidding around. He responds with “well yea I thought we were engaged now” 34 years later and they’re still married. Thought Catalog Logo Mark

About the author

January Nelson

January Nelson

January Nelson is a writer, editor, and dreamer. She writes about astrology, games, love, relationships, and entertainment. January graduated with an English and Literature degree from Columbia University.