June 3, 2025 at 5:23 pm

Boyfriend Hid An Engagement Ring In A Glass Of Wine, But The Girlfriend Saw It And Played A Trick On Her Entire Family

by Jayne Elliott

woman holding wine glass with engagement ring on her finger

Shutterstock/Reddit

Imagine a public wedding proposal at a fancy restaurant.

The boyfriend gets down on one knee and everyone cheers when the girlfriend says “yes.”

That’s not at all what happened in this story.

Instead, what was supposed to be a sweet proposal at a fancy restaurant actually left the entire family upset at the bride to be.

Let’s see what happened.

AITA for how I reacted when my sister pretended to shallow her engagement ring during her marriage proposal ?

My (27f) sister Bailey (30f) is a very unique individual.

She is full of surprises, and is usually a joy to be around.

In our family, it is not secret that my sister has said she actually prefers a public proposal.

She has said she wanted a cheesy ring-in-the-wine proposal in a fancy restaurant with all her family watching.

The dinner was on our parent’s wedding anniversary, to make Bailey’s proposal a surprise.

Bailey was on to them!

My mom (49f), dad (52m) and I were at the dinner with Bailey and her then boyfriend Brain (31m).

When the wine came, Bailey was looking at away, stretching her neck, and looking like she wanted to get up.

What was unknown to the rest of table is that Bailey had suspected that Brain was going to propose propose.

When she had spotted the ring when the waitress was carrying the wine, she saw an opportunity.

She fooled them all!

While we were distracted looking at what Bailey was appearing looking at, she suddenly drank the wine like a shot.

She grabbed her neck and, to me, her face looked like she was choking.

She will later say she was pretending to swallow the ring, not pretending to choke.

Because of my training, I jumped got in position to do the heimlich maneuver.

Talk about a strange proposal!

Bailey spat out the ring on the 1st pull and she was laughing.

It took everyone an embarrassingly large amount of seconds to realize that Bailey was never choking.

Bailey placed the ring on her finger and said yes.

Brian looked too stunned to speak.

Now Bailey is pointing blame.

My parents didn’t voice their disappointment at Bailey that night, but afterwards they did.

Although they’re engaged, Bailey’s relationship with Brian has been rocky.

One day, Bailey surprised me again by confronting me.

She blamed me for Brian and our parents being annoyed by her.

She said I overreacted and scared everyone.

She said she wasn’t pretending to choke.

She said she was pretending to swallow the ring, and her holding her neck was her pretending that wasn’t going down smoothly.

She said it’s my fault everyone thought she was pretending to choke.

Am I the jerk ?

Bailey went too far by scaring everyone. What was meant as a joke clearly didn’t land.

Let’s see how Reddit reacted to this story.

This person would’ve done the same thing.

Screenshot 2025 05 20 at 4.12.23 PM Boyfriend Hid An Engagement Ring In A Glass Of Wine, But The Girlfriend Saw It And Played A Trick On Her Entire Family

Yes, I’m sure she meant swallow too.

Screenshot 2025 05 20 at 4.12.44 PM Boyfriend Hid An Engagement Ring In A Glass Of Wine, But The Girlfriend Saw It And Played A Trick On Her Entire Family

This sounds like a warning.

Screenshot 2025 05 20 at 4.13.01 PM Boyfriend Hid An Engagement Ring In A Glass Of Wine, But The Girlfriend Saw It And Played A Trick On Her Entire Family

Her sister needs to take responsibility for her bad joke.

Screenshot 2025 05 20 at 4.13.15 PM Boyfriend Hid An Engagement Ring In A Glass Of Wine, But The Girlfriend Saw It And Played A Trick On Her Entire Family

Her prank wasn’t funny.

Screenshot 2025 05 20 at 4.13.28 PM Boyfriend Hid An Engagement Ring In A Glass Of Wine, But The Girlfriend Saw It And Played A Trick On Her Entire Family

Talk about a bad marriage proposal!

So incredibly cringe.

If you enjoyed this story, check out this post about a daughter who invited herself to her parents’ 40th anniversary vacation for all the wrong reasons.