15 Creative Ways to Propose to Your Bridesmaids (Plus An Easy DIY Project!)

They’ve been with you through thick and thin and now you’re ready to make it official, with your bridesmaids that is! Your bridesmaids, especially your maid-of-honor, will be crucial to you throughout your wedding planning process and the day of, so we’ve rounded up some genius ways to ask your bridesmaids.

I Choo-Choo-Choose You

Choo Choo Bridesmaids

Photo: Etsy.com

When you’re only options are “Yes! I’m on board” or “No, I suck,” the answer is obvious. There’s no harm in a little humor!

Ring Pop

Ringpop Proposal

Photo: Etsy.com

Who needs diamonds when you can have candy? Pop the question to your maids with a ring pop!

Cupcake In A Jar

Channel your inner Marie Antoinnete and “Let them eat cake!” Download the templates here!

Confetti Envelope

Get the party started as soon as they open the envelope with a blast of confetti!

Locket Rings

They also double as wedding day jewelry!

A Friendship Diamond Candle


This sweetly scented candles burns down to reveal a ring inside, plus a code which your bridesmaids can enter to win a ring worth $100, $1000 or $5000 online!

Buy here: Friendship Ring Candle, $25, DiamondCandles.com

Mystery Egg

Egg Surprise

Photo: Etsy.com

If the bridesmaid silhouette doesn’t give it away, then the message inside will. Order the eggs here.

Personalized Crossword Puzzle

Personalized Crossword

Photo: Etsy.com

Remember the good times with a crossword puzzle where the clues are times you and your future bridesmaid shared together. Order a puzzle here.

Star Bracelets

Got the Script Need The Stars

Photo: Etsy.com

The cards read, “I’ve got the script, but I need the stars.” Nothing woos a bridesmaid like the red carpet treatment!

Jumble Cookie Puzzle

Once your bridesmaids put it all together, the question is revealed. Plus points for being edible! It’s easy to put photos on cookies these days with services like Insta-Graham or DIY it with instructions from E-How.com!

Hidden Message Pashmina

Not only will this pashmina keep your girls warm and cozy, but they’ll always have something to remember you by! The words create a cool pattern, but unfolded they reveal your question. Order the pashminas here.

A Fortune Cookie

Felt Fortune Cookie

Photo: Etsy.com

This fortune will predict where you’ll bridesmaids will be in a few months…at your wedding!

Paper Dolls

Paper Dolls

Photo: Etsy.com

You’re never too old to play with dolls! You can mix and match these custom cut-outs to represent your bridal party, too. How fun!

Box of Goodies

Prep your bridesmaids for their duties by arming them with pretty wedding things (like a handkerchief for tears and color palette swatches for their input) plus sentimental photos and trinkets documenting your friendship.


Your bridesmaids are there to make sure you don’t unravel before the big day.

Find out how to make your own Bridesmaid proposal with this step-by-step DIY!

> 4 getting ready ideas for your bridesmaids

> A “Will You Be My Bridesmaid” proposal video

> Shop bridesmaid gifts!