Creative Ways to Ask, “Will You Be My Bridesmaid?”

After your fiancé popped the big question, and you’ve started wedding planning, there is another important proposal that needs to take place. It’s time to ask your best friends and loved ones, “Will you be my bridesmaid or maid of honor?”

Your bridesmaids have undoubtedly been your rock in life, and they will continue to do so throughout the whole wedding planning process. As a way to show your love and appreciation for their role in your life, it’s a sweet gesture to give them a creative bridesmaids invitation.

Here are just a few memorable, witty, and surprising ways of popping the question to your bridesmaids. Have fun with the process and tailor some of these unique ideas for asking your besties to be a part of your special day.


puzzle pieces
Wistfully Modern

Creating a puzzle with Wistfully Modern is a memorable way to invite those closest to you to join your bridal party. This keepsake is the perfect way to surprise your friends and get them excited about your big day. 16 random puzzle pieces spell out, “Be my maid of honor?” for them to put together to solve the jumble. Once the puzzle is solved the recipient can glue down the pieces and extra embellishments down on the linen for an organic invitation to keep.

Proposal Box

Bridesmaid Box

There are a variety of proposal boxes you can explore online for your bridesmaid’s proposal. You can gather inspiration and create your own personalized box or choose from one of these fabulous sets below.

Bridesmaid Box
White Confetti Box


Survival kit
Sweettalk Designs

Instead of a proposal box try making a bridesmaid’s survival kit? This humorous method will get some laughs, and come in handy if you’re ever a bridezilla.

Bling Her Out


Who doesn’t love a new piece of jewelry? From a customized bridesmaid’s charm to a sparkly bangle, jewelry is the way to go.

Sweet Tooth

Sweet Philosophy

If you swoon over anything related to Paris or maybe just watched one too many reruns of Gossip Girl, then why not customize a box of stamped macarons? This sweet treat is sure to be the perfect recipe for a maid of honor to say yes.

Cupcake in a jar
Sweet Sisters Cupcakes

Try a fresh cupcake in a jar to add some more flavor.

Cheers with Wine

If you’ve been best friends for years, then you’ve most likely cracked a bottle of wine—or 50—together. Pop the bottle and cheers to her acceptance as your maid of honor or bridesmaid, or let her save it for a stressful day of wedding planning with you. You can customize the label with a picture of you two for an added personal touch. If your wine isn’t your bestie’s thing, then opt for champagne, liquor, or even a bag of coffee.

Wine glass

Add in something extra with a personalized wine glass.

Balloon Kit

Balloon kit
Find here!

Pop the question, while your friends pop their balloons with this sweet set from Petite 25, or you can make your own. This is a fun way to ask those special women in your life by hiding a secret message inside a balloon full of confetti.

Will You Be My Bridesmaid?

Bottle of wine
Cleary Lane

After you’ve selected your maid or matron of honor and bridesmaids, it’s time to ask them to accept the role officially. While there are endless ways you can ask the question, why not make it one to remember? Instead of sending a text or facetiming your friends, send them a fun invitation. Choose a way that speaks to your relationships, like a bridal party bracelet or bridesmaid proposal box. Whatever creative method you choose to ask, “Will you be my bridesmaid?” will be memorable, and more importantly, your friends are sure to say yes!

Rebecca B. Lawrence

About Rebecca B. Lawrence

Rebbeca has been writing about weddings, jewelry, and fashion for years. Her favorite place to hang out, aside from this website, is Pinterest. She loves Art Deco Jewelry, beach-themed weddings, and anything related to the British Royal Family.