When Romance Meets Humor: Hilarious Engagement Stories

Some girls fantasize about a romantic proposal in Paris or a five-star hotel room filled with rose petals and champagne. These may sound like a romantic cliché proposal, but nothing beats creative and funny ways to put the ring on a woman’s finger. When romance meets humor, will it be a recipe for disaster or a hilarious epic moment? We’ll take a trip down the memory lane of funny engagement stories that will make you laugh out loud.


Funny Engagement Stories


My then-boyfriend and I were having drinks in a bar, and we can’t help but overhear a conversation. The bartender said four policemen stormed into the bar last night and handcuffed a random guy, and violently shown the use of force.

I lost respect for the cops in that town and continued drinking the whole night. A few hours later, six SWAT members entered the bar, handcuffed my boyfriend, and dragged him in the middle of the bar. They knew his name, and the ‘police brutality’ story was still fresh in my mind. I held on to one of the SWAT members and demanded a warrant of arrest; he handed me a piece of paper that says, “Will You Marry Me?”.

I said YES; I had high blood pressure at the end of the night, and we ended up inviting the whole SWAT team and the conniving bartender to our wedding.

– Jamie, 36

Plan Your Own Proposal

One of my male friends asked for my help to orchestrate a marriage proposal. I planned the whole thing, from the flowers, outfit, scenario, music, and decorations. I called the beach resort, the destination of the proposal, and even asked help from the management.

Everything was planned perfectly, and it was so romantic. When the music cued, the spotlight focused on me, and I saw my boyfriend kneeling on one knee. All this time, I was planning my proposal!

Of course, I said yes. How can I say no to my wise boyfriend who let me plan my own proposal? He let me do all the work to get the proposal of my dreams. My friends and the resort staff found it hilarious. I was all sweaty and looked tired from all the preparations on the day of my engagement. Sweet but annoying!

– Hailey, 28


Christmas Carole

My brother proposed to his long-time girlfriend on the 30th of December, and we decided to serenade her the old school way. We had a guitar, a percussion beatbox, some shakers, a portable microphone, and practiced our song numbers.

As my brother started to sing his first song, ‘I wanna grow old with you,’ I heard her dad shout, “Give them 20 dollars and make them go away; their sound is killing me”. It was hilarious! They thought we were Christmas carolers and thought we sound terrible. Five years and two kids later, my brother still sounds terrible when singing.

– Rhea, 34

He Dropped it Into a Raging River

This is not my story, but my friend’s. Her boyfriend took her for a walk and stopped at a place by the river. He kneeled and as he was digging into his pocket, my friend was getting teary-eyed. He was so nervous that as he got the box out of his pocket, he dropped it into the river!

My friend started to panic and freak out, leaning over the railing and said frantically they should go after the box. Her bf, still kneeling, took out a second box, this time with the real ring in it, laughing and finally popped the question.


Funny Engagement Stories Last a Lifetime

Romantic or funny, engagement stories are always something couples love reminiscing about. If you are ready to pop the question, you can think of romantic ideas or funny ones. Don’t forget to make it even more memorable with a lovely engagement ring that will touch her heart.

Talk to us today to help you decide on that engagement ring that will surely make it an event to remember.

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