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16 Times a Marriage Proposal Went Hilariously Off-Script

Posted on November 27, 2025November 27, 2025 by Amir Khan

A marriage proposal is a moment you want to remember for a lifetime. Usually, it’s carefully planned: the ring, the words, the atmosphere, the perfect shot… But life loves to make adjustments even in the most solemn scenes. These stories are about how romance met reality, turning sometimes into comedy or improvisation.

Story1
My girlfriend waited 7 years for my proposal. She hinted that it was time, but I kept dragging my feet. This summer, I finally decided to do it.
I prepared a romantic proposal for over a month! In the end, she told me that it’s time for us to break up because she has someone else. I’m speechless… © Not everyone will understand / VK

Story2
My friend Vincent was courting a woman named Natasha. Well, courting in the sense that they had already been living together for 5 months.
One Saturday they were lying in bed, being lazy, each on their own smartphone, and Vincent suddenly realized that he was ready to spend his whole life with this woman. He then turned to her and said, “Natasha, why don’t we buy you an engagement ring?” Natasha, after a couple of minutes, shows him a ring on her smartphone and says, “This one.”
A few days later, they went to the jeweler’s and bought the ring she liked, and a ring for Vincent as well. After several years of marriage with Natasha, Vincent said, “I really love that trait of hers: she knows exactly what she wants.” © PolAnd1234 / Pikabu

Story3
My mom wants to propose to my dad after being together for 27 years. She never wanted to get married because she’s shy and didn’t want the hype to be about her relationship. On the other hand, my father always asks her to marry him, since he’s always wanted to get married.
My mother is terminally ill and has less than a year to live, according to her doctors… She now wants to propose to him, to finally give him a wedding before she leaves us. I am helping her plan her proposal: she wants to do a small, meaningful, in the snow (we’re Canadian) gesture for him to announce him she finally wants to get married! © Elegant-Ad6853 / RedditStory4
My significant other is a super hands on, loves to build and fix things kind of guy. He actually built me a set of nutcrackers for Christmas that I unwrapped in front of my whole family on Christmas day. He spent hours making these nutcrackers look like us. His nutcracker was down on one knee, offering a crown to my nutcracker; essentially asking her to be his queen.
After I opened it, he got down on one knee and proposed. So now I have those nutcrackers to remind me of his proposal which was just so his personality, and it couldn’t have been lovelier. © kikat / Reddit

Story5
My mom was dating a guy from university, everything was serious, they loved each other, but his mother couldn’t stand her. This guy proposed to my mom. It was a beautiful evening, very romantic, he got down on one knee, took out a ring, and asked, “Will you be my wife?”
Mom thought about it and said, “Yes.” But then he added, “Phew, great! Even though my mom wanted me to find a blonde…” And immediately she replied, “No.” And broke up with him.
Now she jokes that she was one step away from a life with a weirdo. © Not Everyone Will Understand / VK

Story6
I’ve been living with my boyfriend for over a year. When I asked, “When are you going to propose?” he just gave me a withering look and said, “Couldn’t you have waited a couple of hours?” He took a ring out of his bag, got down on one knee, and opened the box. And there I am, standing by the stove, with a spoon in one hand, crying. © Not Everyone Will Understand / VK

Story7
Pilot here. A guy asked me to fly him and his significant other over a field, where 150 people had formed a heart and 2 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. © apiratenamedbob / Reddit

Story8
My best friend just got engaged and when her significant other proposed, they were in a little French deli. She had just put a massive mouthful of pie in her face when she saw he had got down on one knee.
She was so shocked she spat the pie out all over herself, all over him, all over everything. She just sort of nodded — it was very like her to do something like that so it’s all fine but still — I don’t think he was expecting pie in his face. © Unknown author / RedditStory9
My boyfriend and I were in Verona. It’s impossible to convey the beauty of this place; there’s something enchanting about this city. As we stood near Juliet’s House, he asked me:
— Do you like it here?
— Absolutely.
— Shall we come here for our anniversary?
— Which anniversary?
And then he got down on one knee and pulled out a ring. We’re getting married! © Overheard / Ideer

Story10
“A dating app brought us together, and now we’re engaged. I surprised her with a flying dress photoshoot and proposed during it. Feeling extremely lucky.” © Jtaco88 / Reddit
You know, I waited a long time for my boyfriend to propose to me. He promised to do it on February 14th, but then decided to wait for my birthday. And so, on the appointed day, April 3rd, everything seemed perfect: a restaurant, a ring, a knee. What more could you ask for?!
But in a moment, I realized I didn’t want to spend my life with him. I wanted someone else to be there… I never thought decisions could change so quickly, I ran out of the restaurant, and we broke up.
It turned out I was just in love with someone else — my colleague. The strangest thing is, it turned out to be mutual, and now I am truly happy. © Not everyone will understand / VK

Story11
I think my mom has some weird priorities. I spent a long time planning to propose to my girlfriend, bought a ring, and finally, it happened. I came home in the evening.
Me: “Mom, I proposed to Anna!”
Mom: “Alright. But when are you going to dust your room?” © Killer Stories / VK

Story12
I had the ring in my hand, I was saying how happy she made me, and how I wanted us to be together forever. And then she interrupted and said, “Will you marry me?” And I said yes and put a ring on her finger.
Then I said, “Hang on, that was my line.” And she said, “Sorry, I got excited.” Then she cried a lot. © Cosimo_Zaretti / Reddit

Story13
I got pregnant, gave birth to a beautiful daughter. My significant other came over, got down on one knee. I was already prepared to say yes. But there was a glitch in the system, and instead, he said, “Will you have more children with me?” © Not everyone will understand / VK

Story14
My boyfriend proposed to me. Not in a café, not in a park, not at some concert, but right in a blanket fort!
We were sitting at home during the weekend, with nothing to do, recalling our childhood, though both of us are over 25. We built a big fort in the living room out of pillows, blankets, and chairs. We sat there sharing funny childhood stories, and then he got down on one knee and pulled out a ring box.
At first, I couldn’t believe it, but a few seconds later, I realized it was all real. Now I’m bragging to my friends that I’m a “fort bride.” © Caramel / VK

Story15
“Here’s how I proposed. She said yes.” © edebby / Reddit
“Your girlfriend must be the team Seeker because you, my friend, are a Keeper! Congrats!” © alpacapalooza13 / Reddit
Once, when I was head over heels in love, I decided to propose to my girlfriend. I crafted the proposal in the form of a poem, folded the sheet of paper into an origami swan, and hid it in a bouquet which I presented during a date.
She found the note immediately, unfolded it, and read it right there in the subway car. I don’t remember the first stanza, but the second went like this:
“My heart full of emotions
Decided it wants to be yours.
The flame of my love is burning.
Tell me, will you marry me?”
— Are you serious? — she asked, glancing around with curiosity and caution, as if expecting further developments and feeling caught off guard.
— Yes, I’m serious, — I confirmed. But there wasn’t even a ring. It was just me, waiting for an answer.
Soon, I received my rejection and painfully recovered for nearly 6 months. I have no regrets, as the stanza turned out to be quite good. © Vecherin / Pikabu

Story16
Once, my boyfriend and I decided to go to the park. There were kids playing soccer, and we decided to relive our childhood: I stood in goal, and my boyfriend joined the kids in kicking the ball around.
Then, my boyfriend got down on one knee in front of me and pulled a ring out of his pocket. In my excitement, I forgot that we were playing soccer. Then, out of the corner of my eye, I saw a soccer ball coming right at me…
Eventually, I ended up with a broken arm and at the hospital, but on the bright side, I am soon marrying the love of my life. © Overheard / Ideer

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