Will You Be My Bridesmaid? 12 Delightful Ways to Pop the Question

You’re happily engaged and eager to get started with wedding planning. But first, there’s a big question you need to ask a few special people — “Will you be my bridesmaid?” No matter how excited you are to ask them, it’s not always easy to know the best way to do it. 

Fortunately, we’re here to help you find the perfect way to pop the question. We’ll explain when to ask, how to ask, and what to include in your bridesmaid proposal card. Plus, we’ll share some of our favorite designs — so all you need to do is add your own personal touch. 

When to Ask Someone to Be Your Bridesmaid

Your bridal party — particularly the maid of honor or matron of honor — plays a crucial role in supporting you through the wedding planning process, including the bachelorette party and bridal shower. That’s why it’s a great idea to get them involved as soon as possible. Aim to pop the question at least six months before your big day so they have enough time to prepare and plan accordingly. 

12 Fun Ways to Ask Someone “Will You Be My Bridesmaid?”

Now that you know when to ask, it’s time to get to the exciting part — how to ask! Here are some of our favorite ways to ask someone to be part of your bridal or wedding party. While we’re focusing on bridesmaids, keep in mind that you can also apply these ideas to other members of your wedding party, including the maid of honor, groomsmen, flower girl, ring bearer, and other key supporters.

1. Give a “Bridesmaid” Keepsake Gift

Lots of brides and grooms love to give their wedding party members a gift when they ask them the big question. Popular bridesmaid gifts include skincare gift sets, jewelry and pretty hair ties (to wear on the wedding day), tote bags, personalized tumblers, stemless wine glasses, and notebooks. If you can give a keepsake gift like a personalized jewelry box or monogram towel, then even better — they’ll always remember the moment you asked when they see it.

2. Send a Letter in a Bottle

As a fun twist on handing a note to your future bridesmaids, why not send them a message in a bottle instead? Get some tiny message bottles, grab a few sheets of paper, and handwrite “Will you be my bridesmaid?” Pop the notes into the bottles, seal them, and hand them to your bridesmaids-to-be for an unforgettable moment.

3. Surprise Them at Their Doorstep

What better way to make your bridesmaid proposal than to show up at their doorstep as a surprise? Arrive with a bouquet of flowers in hand (and perhaps a bottle of wine or sparkling juice) and ask your bestie to be your maid of honor or bridesmaid. You can toast the moment when she says yes!

4. Create a Personalized “Will You Be My Bridesmaid?” Print

Personalized prints make wonderful wedding gifts, but they’re also a sweet way to ask someone to be an extra-special part of your wedding day. Look online for a beautiful print that you can customize with the bridesmaid’s name and the date of your planned wedding day. 

5. Surprise Them with Personalized Jewelry

Jewelry is a lovely gift idea for almost every moment, but it’s especially fitting for a bridesmaid proposal. If you’re on a tight budget, sites like Etsy have a variety of handmade jewelry pieces that won’t break the bank. Choose delicate gold bracelets or necklaces with the bridesmaid’s initials or opt for earrings that match your wedding colors. 

6. Send Cookies or Cupcakes

For a bridesmaid proposal idea that’s sweet and tasty, it doesn’t get better than delicious cookies or cupcakes. Bake your own at home, then with icing, you can write the words “Will you be my bridesmaid?” You can ice each cookie or cupcake with individual words or try fitting the question all on one (depending on the size)! Or you could order custom-made sweets and let the pros handle it all. Whichever option you choose, your besties are sure to smile when they open the package. 

7. Ask Them Over Dinner

Invite your besties to a dinner party at your place. Whether you cook up a homemade meal or order from a restaurant, don’t tell them the reason for the dinner — just say you want to hang out. Then, as dinner comes to a close, pour some bubbly and bring out a cake iced with the question “Will you be my bridesmaids?” It’s sure to be a night to remember.

8. Put Together a Bridesmaid Proposal Box

While you can buy a prepackaged bridesmaid proposal box, consider making a personalized version if you have the time (and crafty skills). To put together a DIY bridesmaid proposal gift box, all you need is a note and some goodies to fill the container — chocolate candies, face masks, notebooks, scented candles, and cozy socks are favorites. Decorate the box with stickers and spruce up the interior with confetti and tissue paper that matches your wedding theme. 

9. Send a Bouquet of Flowers with a Note

You can’t go wrong with flowers, and they make a wonderful bridesmaid proposal gift idea. Order a bouquet of beautiful blossoms and have them delivered to your future bridesmaids along with a personalized message that ends with, “Will you be my bridesmaid?” For a contemporary (and longer-lasting) twist on sending flowers, you could send a houseplant, succulent, or terrarium instead. 

10. Surprise Them with a Bridesmaid Robe

We’ve all seen those wedding day photos with the bride and her bridal party wearing matching personalized robes. Surprise your would-be maid of honor and bridesmaids with their very own robes as the perfect way to ask them to take on the role of standing by your side on the big day. 

11. Give a Personalized Wine or Champagne Bottle

Wine makes a great gift for any holiday or celebration and you can step it up with a personalized wine label. Simply buy your (or your soon-to-be-bridesmaid’s) favorite bottle of wine or bubbly. Then, affix a customized wine label with the words, “Will you be my bridesmaid?” If you have the budget, you can present the bottle with a pair of champagne flutes or wine glasses.

12. Send a Bridesmaid Proposal Card

The best way to ask someone to be your bridesmaid is often the simplest. A heartfelt bridesmaid proposal card is sure to make their face light up. Make your own card and mail it to someone special, or send a digital card to your would-be bridesmaids. Greenvelope lets you choose from hundreds of customizable digital cards that you can personalize and send in just a matter of minutes.

Message Ideas for Your Bridesmaid Proposal Card

Whether you give a gift or not, chances are you’ll be sending a card to ask someone special to be your bridesmaid or maid of honor. Naturally, you can simply ask, “Will you be my bridesmaid?” But if you’d like to add to that question or change it up a bit, here are some ideas to inspire you. 

• Will you be by my side on my wedding day, [Name]?
• I couldn’t do this without my best friend. Be my bridesmaid?
• Wedding planning is going to be so much fun with you! Please say you’ll be my bridesmaid!
• Be my bridesmaid, bestie?
• Excited to tie the knot with you close by, [Name]. Will you do me the honor of being one of my bridesmaids?
• We’ve been BFFs forever, now it’s time to make you my bridesmaid! 
• I’d love to have you by my side on the big day. Will you be my maid of honor? 

Bridesmaid Proposal Cards: A Few Favorites

Sending a digital card from Greenvelope means that you can customize any design however you wish. Whether it’s a congratulations card or a wedding invitation, you can transform it into your dream bridesmaid proposal card. Update the font, select a color, and add your own personal message. You can send it to your loved one as soon as you’re done. 

Here are a few designs that can easily become a beautiful bridesmaid proposal card. 

Put a Ring On It Card

Design: Claudia Owen

This eye-catching ring-shaped design makes perfect sense as a bridesmaid proposal card. Swap out the text for “Will you be my bridesmaid?” and send it on its way to your future bridal party members. 

Happy Paint Speckles Card

Design: Signature Greenvelope

This happy paint speckles card is so cute and works beautifully for any occasion — including a bridesmaid proposal. Choose your favorite color option or work with our designers to add a personal touch with your own color palette. 

Round of Applause Card

Design: Signature Greenvelope

We love the gold foil effect on this round of applause card. Keep the cover text as it is, or change it to something totally bespoke. There’s lots of space on the reverse for the big question as well as a longer message if you wish. 

Ask “Will You Be My Bridesmaid?” Your Way

Use these bridesmaid proposal ideas and wording tips to help you put together the perfect bridesmaid proposal moment. Whether you send a digital card or host a dinner party for your best friends (or both), what matters most is the excitement they’ll feel when you share the news. 

Explore our collection of wedding cards and invites to find a design you love, then customize it to suit the occasion. And remember: with your BFFs by your side, you’re sure to have the most special day ever.