Bridesmaid Proposal Ideas: 21 Creative Ways to Pop the Question

Get inspired by these fun ways to ask, "Will you be my bridesmaid?"

Updated 01/10/19

Photo by Laurken Kendall

You're engaged! Now that you’ve said “yes” to your perfect partner, it’s time for one more important proposal: Your bridesmaid proposals! Need some inspiration? Get ready to pop the question to the VIP ladies in your life with these creative bridesmaid proposal ideas.

Here are our favorite ways to ask bridesmaids to be in your wedding.

Throw a Wine Night

One of our favorite festive bridesmaid proposal ideas is to gather your group for a wine tasting or drinks night at your home. Andrea Freeman, founder of Andrea Freeman Events, recommends waiting until the end of the evening to present the final ready-to-sip selection: a delicious white or red varietal with a custom label that playfully asks the imbibers to be in your wedding party. Needless to say, you'll be toasting yourselves the rest of the night.

Break Open Fortune Cookies

Aviva Samuels, founder of Kiss the Planner, keeps food and beverages in mind when it comes to asking pals the big question. "Invite the gang over on the pretense of enjoying some takeout Chinese food and a movie,” she says. “When it comes time for the fortune cookies, hand out custom-made sweets—you can buy them online—with 'Will you be my bridesmaid?' on the little white fortune paper inside."

Bling Out Your Besties

Sarah Chancey, founder of wedding planning and design company Chancey Charm, recently helped stage a bridesmaids' luncheon that celebrated the bride-to-be's true "gems" in her life. The gemstone theme naturally lent itself to a bright color scheme, finger foods that were a feast for the eyes, and a piece of jewelry for each woman who was asked to be a part of the wedding day.

Set up a Coffee Date

Can't get the squad together all at once? Don't fret. Organize a special coffee date with each person at one of your favorite shops. Bring along a personalized mug or ask the barista to write the question, rather than your friend’s name, on the cup. Just make sure your pal reads it before she drains her java.

Pack a Gift Box

If quirky or nontraditional gestures aren't your thing, a simple gift box filled with wedding-related items is a safe—and thoughtful—bet. Fill the box with a mini bottle of bubbly, nail polish, sheet masks, and other sweet treats along with a handwritten note from you. Let each person know how much their relationship means to your life, share some memories, and explain why they are so deserving of a spot in your wedding squad.

Present a Picture Frame

You can't go wrong with photo of you and your future bridesmaid (or bridesman!) in a beautiful frame. The photo can either be of just you and the person or, if you and your tribe are all friends with one another, it can be a group photo. Whatever you choose, they’re sure to say "yes!"

Say It With Balloons

Who can say no to a fun balloon? Tessa Lyn Brand of Tessa Lyn Events suggests a twist on a party balloon: Hide the message inside. “Give a little box, each with a small inflated balloon and a safety pin,” she explains. “When they pop the balloon, they’ll find a message that says, ‘Now it’s time for me to pop the question!’” You can even add confetti or glitter to the balloon for an added surprise.

Send a Scratch-off Card

For a fun game, create a custom card with a portion that scratches off. Include a penny in the envelope for the scratching. Under the scratch-off part of the card, your friends will find a message asking them, "Will You Be My Bridesmaid?" As for you, well, you win the jackpot.

Vow to Be a Bridechilla

Your friends are giving their time and effort to help you out for your big day, so why not give them something back right from the start? Jen Glantz, the founder of Bridesmaid for Hire and author of All My Friends Are Engaged, suggests writing vows to each of them as you pop the question. "When you ask them to come along with you on this often chaotic and emotional wedding adventure, lay out a funny list of 10 'vows' that you promise not to do or act like during this time,” Glantz says. “Call out the fact that if you do begin to freak out, you're hoping they snap you back into place like they have done time and time again throughout the years."

Gift a Gag Wedding Book

If you're wondering how to ask your favorite people to be in your wedding party in a hilarious way, gift a cheeky wedding-related book. There’s is no shortage of tomes like 101 Uses for a Bridesmaid Dress or the fictional Bridesmaids to present alongside the big question. Camille McLamb, founder of Camille Victoria Weddings, recommends inscribing a personal note on the inside for each person, and feel free to make it playful.

Ask In Person

All this pomp and circumstance not your thing? “The bridesmaid proposal doesn’t require a lot, just a sweet message to let her know how much you value the friendship,” explains planner Shannon Leahy. She suggests sticking to a personal monologue on why you want this particular person to be part of your day. It’s the heartfelt part that matters after all.

Sign Up for a Floral Workshop

Weddings and flowers go hand-in-hand, so consider proposing to your bridal party over some blooms. Bring your crew to a floral workshop at a local shop, says Firefly Events founder Teissia Treynet. She suggests arranging a private event, and stock each station with your friends’ favorite flowers. Attach a note directed to each person asking them to be in your wedding party. For example, address a letter to Lauren and wrap it on the rose, since that’s her go-to bloom. “It’s such a fun way to get creative with your buddies while making them feel special,” Treynet adds.

Bonus points: Bring along the bubbles.

Throw a Boozy Brunch

Nothing says bride-to-be quite like bottles of bubbles, so plan a morning of mimosas, eggs Benedict, and a very important question. Have your pals meet you at a classic brunch spot, where you can propose to the group over breakfast drinks and plenty of bacon. It will be the beginning of many planning meals.

Share the Insta-love

We announce birthday cheers and holiday greetings via social media, so what better way to acknowledge your friendship than proposing on Instagram? Set up a moment you can share online as you pop the question. “Making a live video of the proposal not only creates excitement for your wedding, but allows guests to follow along your nuptial journey,” explains destination wedding planner Michelle Rago. “Plus, friends and family can react to the news by responding with comments, memes and emojis.” Talk about getting guests to interact!

Fill a Tote With All The Favorite Things

Sometimes it’s best to keep it cute and personal. Fill a Totes a Bridesmaid bag with each person’s preferred treats, such as favorite snacks, beloved beauty brands, or go-to rosé. It shows how well you know each friend, and they’ll be stoked for the gifts along with the big question. Planner Jove Meyer offers great tips for this proposal idea: Claim holiday or birthday greetings as the excuse to gather each person’s address, and to make sure there are no hurt feelings, send them all at the same time.

Set a Tea Time

Don your most feminine fascinator and floral print dresses as you and your favorites sit down to afternoon tea. Along with scones and clotted cream, petit fours, and cucumber sandwiches, share with your crew just how much they mean to you—and how much it will mean for them to stand alongside you as you say “I do.” The best part? Afternoon tea often comes with Champagne!

Start the Robe Life

Stage that popular photo of your gals in matching robes right from the start: by gifting them each a robe as you ask them to be in your party. Go floral print, flannel, stripes, or just classic white terrycloth with monograms, but one thing is for sure: your girls will love the comfy gesture as much as they will adore being your nearest and dearest on the big day.

Say it With a T-shirt

We’re suckers for funny t-shirts, so get creative making a witty tank for your wedding party to rock throughout the planning process. Peruse customizable websites like Etsy, where you can comb through shirts with catchy phrases like “Bride’s Babes” and “Nacho Basic Maid of Honor.” Give each wedding party member a tee as you pop the question.

Relax Over Mani-Pedis

Treat your pals to an afternoon at the nail salon along with a sweet surprise: a bridesmaid proposal. Gift each gal a wedding-focused color, such as Essie’s Bachelorette Bash, as you explain that they’ll all need to wear it during the celebration since they’ll all be bridesmaids. Mini spa day commence!

Open a Box of Macarons

These sweet confections ooze girly perfection, which is why they are an ideal way to propose to your bridesmaids. Plan to send each person a box of varying flavors, but before you drop them in the mail, have a calligrapher write out “Will you be my bridesmaid?” in edible glitter on the cookies, says planner Jennie Maretti of Pixies & Petals. As she adds: “Food is always popular.”

Sip Cocktails and Eat Canapés

Hello, wedding soirée! It’s time to get fancy. Invite your VIPs to an evening of craft cocktails and bite-sized nibbles while you request the honor of their presence—as bridesmaids and bridesmen. Throw the event at your favorite local cocktail joint, especially if their have a private party room, or make it at-home affair. Just hire a bartender to keep the drinks flowing, so you can focus on the enjoyable stuff: planning the wedding with your newly minted bridal squad!

Related Stories