The Weirdest And Worst Marriage Proposals People Have Ever Witnessed

Some people don't understand the concept of timing, location, and what their significant other would like to happen when it comes to proposals. These cringe-worthy proposals share just how awkward and uncomfortable it can be to watch without outwardly judging...

Don’t Propose At A Super Casual ‘Restaurant’

1) “This one was awkward… I was eating dinner at an Applebee’s at one of those high tables near the bar. Sitting at the bar was a couple. After a few minutes, the guy pushes his chair back and gets down on one knee. He starts to propose. Just then, a waiter walks around the corner, trips over the groom-to-be’s outstretched leg and drops a tray of food, to which he said ‘Oh dang! Did I just ruin what I think I ruined?’ In any case, the girl ended up saying ‘yes.'”

2) “I saw a guy propose to his girlfriend in a Subway at around 9 at night. It was so unbelievably awkward because it was just the three of us in the shop. She said no, the guy cried and I still had to order my sub while they sat there.”

3) “When I was waitressing I saw a guy propose. The restaurant itself would be ooookay I guess… But they weren’t dressed up nicely as for a special occasion, it was only early evening, and their kid was with them massacring the table with crayons etc. She didn’t seem to say yes as they hastily paid the bill and both left very stony-faced. Just left me thinking, dude if you wanna propose over dinner at least get a little dressed up and go in the evening and hire a babysitter!”

4) “We had a golf day as a large group where copious amounts of alcohol were consumed and then we had dinner at the Chinese restaurant, which was part of the club. Now, this was by no means a fancy place, but some guy (not part of our group) had decided it was the appropriate place to propose to his girl. One of the guys in our group who was very inebriated leaned back over to the guy’s table and said in a fairly loud voice, ‘Don’t do it mate, you’re making a huge mistake!’ We all found it hilarious in our drunken state, but I don’t think he appreciated it…”

5) “I have actually witnessed a proposal at a Denny’s. It was about 3 AM after bar close. There were two couples in the restaurant. One of the guys takes a knee, proposes, she says yes, etc. While everyone is clapping I turn to my friend and give him this look that says, ‘I don’t want to say anything, but…Denny’s?’ Two years later the restaurant closed down. I’m sure that’s a sign of what became of that proposal as well.”

6) “I saw a Chinese student propose over a microphone in an all-you-can-eat buffet. It was a very cringeworthy experience. I also felt sorry for the girl who was proposed to in public, with lots of English people sitting around stuffing their faces with ribs. Why propose in public like that? Peer pressure to make her say yes? Forgot to mention that he had a ring under a silver food cover on a trolley. And there was also terrible Chinese pop music.”

Hiding The Ring In Strange Places

7) “I was a restaurant in NYC once with my whole family and there was a couple at a table across from ours. The man had the restaurant bake a ring into a cake which was to be presented to his girlfriend so he could pop the question. The wait staff made this known to likely the entire restaurant so when the cake was brought out all eyes were on them. The woman proceeds to cut into the slice of cake finding the ring. She looked mortified. You could see the ‘Are you freaking kidding me face’ on her a mile away. She said no. Promptly placed the ring on the table and left the restaurant, leaving the man behind with his head in his hands. He sat there for 20 minutes or so before paying his bill and leaving.”

8) “My buddy got his wife by asking her this way: They went out to dinner in New York at some fancy restaurant, when they finish and head outside there was a limo with Santa Claus holding the door open. He asked if they would like a free ride home, ’tis the season and all so they obviously said yes and got in. Halfway through the drive, the divider window rolls down and Santa hands them a present and closes the window. He tells her she should open it and BAM, ring. They have been married for about 5 years now!”

9) “I was with a few friends at Burger King at around 3 in the morning (yes Burger King of all places) and the only other people who were eating was a middle-aged couple. The woman got up to go to the bathroom and the husband slipped something out of a ring-box into the woman’s burger. When she came back she ate the burger without noticing anything. The man went wide-eyed and told her she just swallowed the ring, and then asked her to marry him. She said yes, and my friends and I burst out laughing.”

10) “Redneck version of this: My dad proposed to my mom by putting the ring on her Busch Light in the fridge. Ahhh, Romance.”

11) “Heard this story from a teacher of mine in junior high. Boyfriend comes home from work and asks for a foot massage. The ring was hidden in his sock and was somehow flung across the room as she was removing it. ‘Oh…be still my beating heart.'”

12) “My dad stuck the ring in a stick of deodorant, then told my mom she needed to use it. A small argument ensues when mom tells dad she does not need it.”

Retail Store Quality Engagement

13) “I proposed to my (now wife) at Bass Pro Shops in Grapevine, TX. ‘If I can have fun with you in Texas, I can have fun with you anywhere.'”

14) “I was working as a cashier at Walmart, in the ‘express lanes’. Located in redneck suburbs, a gentleman, this description of him is a gift. He bought a $100 ring from me, the jeweler had to bring it to my register and asked me to cut off the price tag with a pair of scissors I had at my register. He paid for it in crumpled change. Then he runs to his girlfriend and her family, this couple is either in their early 40s or just look that bad. He slides on both knees to her feet, yells out her whole name and describes how this woman is the most wonderful person in the world. Nobody is listening or even notices except for me. They hug and leave. I ask around to the other cashiers if they had noticed what just happened. Nobody at all knew what I was talking about.”

15) “I didn’t witness this, but a redneck friend of mine proposed to his girlfriend in a Kmart parking lot because he ‘couldn’t wait till Red Lobster.'”

16) “When my mother and I were checking out at Walmart, the man in front of us pulled a ring out of a Walmart bag (as he had just bought it) and proceeded to propose to his girlfriend with the tag still on it. She said yes…”

17) “A friend of mine had another friend of mine film their proposal and then upload it to Facebook. The proposal took place in a parking lot of a local convenience store. The friend proposing got out of the passenger seat, walked over to the driver’s side, opened the door, got down on one knee, and proceeded to propose. It was sweet, however, I would be so angry if my SO proposed to me in a freaking store parking lot, in a parked car.”

18) “When I was a Customer Service Manager at WalMart in a rural redneck kind of area, I had guys ask, not once, but THREE different times if they could use the store’s intercom to propose to their significant other who was inside shopping. Three times we allowed it. Three times a woman would scream and coming running from some random place in the store to the front and accept. My favorite quote: ‘Oh my God you said you were going to pee!’ as she sobs with happy, ‘You tricked me! Yes! I love you so much right now!'”

19) “I worked at a large toy store chain where you construct your own teddy bears (you know it!) and the mostly female employees in the store began to quietly freak out because there was a gentleman who was planning on proposing to his girlfriend in the store, today. Now, if you’ve never been to this bear building workshop, there are several stages- selecting a bear, stuffing a bear, picking clothes, naming it, and paying for it. At each station, we’re ANXIOUSLY waiting for this guy to pop the question. Selecting a bear? Nothing. Stuffing it? Perfect opportunity missed. Dressing it? Nope. Naming it? COME ON, PROPOSAL BEAR!? Nothing. Eventually, they get up to the counter, and as she is PAYING for the bear, he finally proposes. No down on one knee. No ring. He walks up next to her, opens a box with a bracelet inside (diamond bracelet is traditional in orthodox communities), and asks if she will marry him. Not even looking at him, she glances at the bracelet, says “yes”, hands me her credit card, pays, takes her bear, and they leave.”

20) “My friend worked at a Coldstone Creamery and some guy came in during the day and said, ‘I’m gonna come in later today and put 20 bucks in the tip jar. When I do, I want you guys to sing ‘Iron Man’ by Black Sabbath, and then I’m gonna propose to my girlfriend.’ My friend and her co-workers found it strange but agreed. Later that night, the man reappears with the girlfriend at the Coldstone. Awkward eye contact between the man and the co-workers ensues while they wait in the long freakin’ line. He finally gets up to the front and puts the 20 bucks in the tip jar. No one sings right away, so my friend goes for it solo. He goes down on his knee, pulls out the ring, and says ‘Will you Marry me?’ There is a long, silent pause as the workers and all the people at the Coldstone wait. She pulls him off to the side of the store and they have a quick word while everyone watches. They then go out to his car in the parking lot and sit there. For hours. My friend was still working for about 4 more hours that night and he was still sitting out there with her. My friend assumes that she did not say yes. I concur.”

The Most Nonchalant And Un-Romantic Ways Of Asking

21) “I was at a friend’s house hanging out sometime in high school. His parents were not married, but had been together longer than most marriages last. Someone in our teenage group joked that they should get married so that So-and-so wouldn’t have an excuse to act like a bastard anymore. The dad yells from the kitchen to somewhere else in the house: ‘Honey!’ she yelled back: ‘Yeah?’ ‘You wanna get married?’ ‘Sure. Why not.’ ‘How’s next Thursday?’ ‘Can’t. Bridge game. What about Wednesday?’ ‘Sounds good.’ Lo and behold, they were hitched in a non-flashy civil service by the county judge two weeks later.”

22) “My own proposal was kinda horrible; When watching TV I casually asked her if she had ever done it with a married man. When she said no I asked her if she wanted to, and offered her the ring.”

23) “I was sitting on the couch in our apartment, surfing the web on my laptop and my (now) husband was next to me playing L4D (I think that was the game he was playing). It was summer and we were both planning on starting college in a new city together at the beginning of the next year. I was on our future college’s website reading all the forms and stuff I needed to get done when I looked at my now-husband and said rather nonchalantly, ‘We should get married!’ He replied just as casually, ‘Yes, we should.’ I said, ‘How about September or October?’ and he was all ‘Works for me!’ We had a very plain wedding that October and Have been very happily married for almost 3 years since then!”

24) “I’d stormed home from work fuming about changes to our healthcare plan, barged into the laundry room where he was cleaning up the kitty litter and demanded he calls his company’s office manager (who also handles HR as it’s a small company) and ask if they provided domestic partner benefits. He said, ‘We could just get married.’ And then he had to go wash up so we could hug. Yes, my husband is apparently so terrified of his office manager that he’d rather get married than call her.”

25) “Mine was pretty bad by most standards too. We’d been arguing in the car (I was a drunk FOOL) and my boyfriend (now hubby) yells out, ‘I was going to propose to you next month!’ I don’t remember what we were arguing or why, all I remember is yelling back, ‘well you still can!” We both stopped and just stared at each other. After about 30 seconds, he asked me and I said yes. Since I was drunk and we’d been arguing, I made him ask me about a million more times! We have now been married for 5 years and couldn’t be happier. I would have hated a uber gushy, romantic proposal as it’s so not who we are. We’re too sarcastic, too dry and too cynical for any thing like that. I regret that it happened while we were arguing but I don’t regret that it happened. 5 years of marriage and 7 years together, we’re best friends and partners for life!”

26) “My first husband never actually proposed. We’d been talking about the idea that we’d ‘probably’ get married, sure. One day we happened to pass by a jewelry store that happened to be having a sale, he bought me a ring, and engagement just sort of happened. That marriage did last 20 years.”

27) “Some friends of mine who got engaged a few years ago. They were sitting on the couch watching TV, and during the commercial break he turned to her, pulled out the ring, and was like, ‘Marry me?’ She came into work the next morning, and when I saw the ring and asked her about it, she relayed the story all gushingly excited. Apparently, he wanted to ‘surprise her,’ but thought if he set up a romantic situation, she would see it coming. She seemed really happy and they are still happily married several years later, but I told my boyfriend that if he proposed to me that way, I’d make him do it over.”

28) “My husband was pretty casual about the whole thing. We were both drunk and standing outside in the driveway of a friend’s house. He dropped to one knee, put his beer down and asked me to marry him on a whim. No ring was forthcoming, so I said ‘um…okay’ and that was that.”

Over The Top And Public Proposal Ideas

29) “I was waiting in line at the mall to get pictures with Santa, one year. A guy was setting up quietly behind the cameras, he had big poster boards held by his friends that said ‘(photographer,) will you marry me?’ He hollered for her attention and everyone applauded when she said yes. Well, it was cute I suppose but I think a proposal at work would suck. especially in front of a ton of irritated parents and whiny children in a mall during the holidays…”

30) “There was a terrible one earlier this year when a man for valentines day got his proposal put in giant lettering on the side of a large cruise ship coming into Sydney or Brisbane. It was a flashy idea. Shame about the media attention from shows like ‘Sunrise,’ who filmed the proposal. The poor potential wife had no choice but to accept.”

31) “I knew a girl who, at her wedding, the best man and brother of the groom proposed to his girlfriend at the reception just after the first dance. That had to be one of the most selfish, self-centered things I have ever heard.”

32) “I was on a Contiki tour in 2004 that coincidentally landed in Paris on Valentines Day. We were all at the top of the Eiffel Tower and there was about one proposal every 5 minutes or so. On our wait for the elevator down, we witnessed a really nervous guy in the same line who popped the question. Her response, ‘Eww NO getting married is for old people!’ (Cue awkward silence). We decided to take the stairs.”

33) “I proposed to my wife in Times Square on New Year’s Eve (I was going for maximum cheezy!) She was pretty emotional and took a while to believe I was serious (even though I had a ring). This being New York, strangers started shouting at her to ‘HURRY UP LADY, WHAT’S IT GONNA BE? WE DON’T HAVE ALL NIGHT!'”

34) “Many years ago my sister and my cousin and myself decided to watch Spiderman 2 in the theatre. It was busy the first two weekends and here in our local cineplex, they have a special on Tuesday nights, cheaper tickets. So we did not watch the film the opening weekend, but the Tuesday following the second weekend the film had opened. It’s 5 pm and there are about 10 people in this theatre. One of those movie-card screen-shots pops up and I wasn’t even paying attention but my sister nudged me and some guy (worst thing, he’s wearing a Spiderman t-shirt) is on his knee asking his girlfriend to marry him. That was undoubtedly the saddest round of applause I’ve ever been witness to.”

35) “My friend told her boyfriend at the time that she wanted to be proposed to romantically, and with just them two. She reiterated that she did NOT want a public proposal. Later, he gave her a hint of how it was going to happen. It was going to involve something she hated. That’s a good start, right? He did the ol’ Splash Mountain proposal that looked almost exactly like this, with an unflattering facial expression from my friend and all. FYI, she absolutely freaking HATES Splash Mountain. His friends videotaped the awkwardness of them waiting to see the picture because it wasn’t being displayed like all the other pictures. Then when it was shown, he got down on one knee and quickly said, ‘Will you marry me?’ According to him, he also said, ‘live long and prosper’ somewhere in there, too (which wouldn’t be lame if she was into Star Trek as well.) She didn’t tell me until months after the proposal that after he proposed, she cried for days because it wasn’t done in any way she would have liked it. She also had an anxiety attack at Splash Mountain because of all the people staring at her. So yeah, that was a fun time for her.”

36) “Pilot here. Guy asked me to fly him and his SO over a field, where 150 people had formed a heart and two rings. Huge show, I was really impressed. When she saw it, her response was: ‘Look at all those idiots! How ridiculous is that?’He did not ask his question that day.”

Embarrassingly Awkward To Watch

37) “A co-worker proposed to his SO while she was sitting on a Mall-Santa’s lap around Christmas time. Santa apparently was the one that actually presented the ring to her and he was down on one knee. then they proceeded to open-mouth kiss while she was still sitting on Santa’s knee in front of all the kids in line. He paid the elf to take the pictures. One of them you can see both their tongues as just making out like there is no tomorrow.”

38) “During college (and for several years afterward) I rowed gondolas for extra cash on the side. I had seen about 500 proposals during that time. One guy reaches into his pocket, pulls out a ring box and slides it over to her. With a poor attempt at looking nonchalant, he says, ‘so… yeah.’ She sits there silently for a second, looks over to him incredulously and states, ‘really…really?’ He then shrugs his shoulders gives a goofy grin. Clearly perturbed, she sighs loudly and says, ‘Fine.’ They then hug, kiss briefly and proceed to not talk for the remaining 20 minutes. The only “no” I’ve ever had came from a guy who pulled out all the stops. Dinner, Venetian gondola, roses… even a customized message in a bottle to be ‘found’ during the Venetian gondola ride. So when the time comes, he kneels down and pops the question. After what felt like a full minute of stunned silence, she takes that moment to inform him that she is already married.”

39) “We were at a Dewali celebration put on by the Hindi people in our town (my coworker invited our whole office to go), when my boss, Michael, goes up to the DJ, takes a mic, and proposes to his girlfriend, Carol. I was their ninth date, and she just kind of stood there awkwardly and said, ‘Oh Michael… Can we talk about this in private?’ So freaking embarrassing”

40) “My former best friend made his other friends do a choreographed dance routine in the middle of town, then he got down on his knee. The thing is, neither he nor any of the other people knew how to dance. It was one of the most embarrassing sights I’ve seen. What’s better is that he posted it on facebook, pictures, videos, reactions, all that stuff. It was mildly depressing.”

41) “Facepalm moment for one of my best friends who doesn’t know the concept of perfect timing: He and his girl had been together for 5 years then. He planned on proposing to her on her birthday. Unfortunately, just a couple of days before her birthday, her dad died. The wake was scheduled on her birthday. He proposed to her anyway. The way he proposed was rather… sad and embarrassing. The girl was sitting with her mother, and they were both dazed and tired and devastated. He just goes and kneels on one knee in front of her and asks her to marry him. When she didn’t answer right away, he puts the ring on her finger. I don’t know what he expected. I think he wanted to make her happy by asking her to marry him, but the timing…The good news is they’re still together 6 years and some months now. No news yet of a second proposal though.”