Bad Proposals and Rejected Engagement Rings

engagement rings

Ask the question right!

Proposing to the woman of your dreams should be a moment of romance, excitement, love and passion. Squeals of delight, tears of joy or even a state of speechless awe are the types of responses we all hope for as we go down on one knee, open up the box and  show her the diamond engagement ring we’ve agonized about buying. As she says yes you slip the diamond ring over her finger knowing that she’s yours to have and hold forever.

But for some people it doesn’t quite work out like the movies. Their proposal plans are thwarted by poor planning or unpredictable disaster. For others, the girl simply isn’t ready to commit. We thought we’d share a couple funny ones we’ve come across online.

First is one from Cosmo (1.)

Ring Around the…Ow! ”I was ecstatic when my boyfriend of three years proposed. He took me out to dinner, and the actual proposal was really emotional and touching. Even better: He invested in a serious rock for me. When he went to slip the engagement ring onto my finger, it was a little small, but I was so excited that I forced it on. Within an hour, my finger had swollen to twice its normal size, and the ring wouldn’t come off. When my finger turned blue, my fiancé dragged me to the emergency room. The doctor took one look and said he would have to cut off the ring. I cried the entire time. Luckily, we were able to get a bigger band for the diamond the following week.” —Samantha, 27

This second one is also from Cosmo (1)

Gold Digger “My guy and I had been dating for about a year when we decided to go on a vacation to Mexico together. After a romantic dinner on our last night there, we took a stroll on the beach. I was thinking about how much fun we were having when I looked down and saw that he was holding an engagement ring in front of me. We hadn’t been together for very long, and I was so shocked that I screamed, causing him to jump and drop the ring. When he went to get it, it was buried in the sand. We spent 10 minutes digging it up before I could say yes.” —Elise, 30

This one is from a Reddit User courtesy Huffington Post (2)

I proposed to my wife in Times Square at 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 real diamond 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” – evilal

And a final gem from another Reddit User (2) 

A friend of mine was in a relationship for a very long time and they both knew that it was time to get married, they had already discussed it before just not when he would ask and nothing was definite. They go hiking and are sitting on the edge of a cliff and all the sudden he gets down on one knee ready to ask her, but instead he stands back up and screams how he’s too young for this and he cant do it and throws the box off of the cliff. She freaks out about how he just threw away the engagement ring, then he gets back on one knee and takes the actual ring out of his pocket and says “Just kidding lets get married.” – ippy116

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If you have any funny stories about an engagement you saw go badly wrong please send us a message at and we might just publish it.

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