What should I put in my bridesmaid proposal box?

As a general rule of thumb: the more personal, the better. Whether it be a framed photo of the two of you, a monogrammed mug, or a bottle of their favorite bubbly, select items that you're confident your bridesmaids will use and enjoy.

How long after my proposal should I propose to my bridesmaids?

While everyone's timeline and situation is a bit different, it's usually best to propose to your bridesmaids a year to eight months before your wedding day no matter when your significant other popped the question.

What do I write in my bridesmaid proposal card?

Recognize the significance of your relationship and thank your bridesmaid-to-be for being such an integral person in your life. Most importantly, end the heartfelt note by popping the question: "Will you be my bridesmaid?"

30 Creative Bridesmaid Proposal Ideas

bride and bridesmaids in mismatched dresses in front of oceanic vista — Photo by Erich McVey; Floral design by Moon Canyon

Now that you’ve said “yes” to your perfect partner, it’s time for you to pop the question—to your future bridesmaids, that is! You can keep it short and sweet or go with something more elaborate and planned. Whichever way you choose to propose to your bridesmaids, make sure they know the VIP status they hold in your life and, hopefully, on your big day. So, either in person or in a note, tell them how much their relationship means to you, share some memories, and explain why they are so deserving of a spot in your wedding squad.

Need some creative inspiration? Bridesmaid proposals don't need to be fancy, but if you can afford to, it's a nice idea to set aside a small portion of your budget for them. Your friends are giving their time and effort to help you out until your big day, so give them something back right from the start with a thoughtful and memorable proposal. Don't fret if budgets are tight: proposals can fit all kinds of budgets. If you have a smaller entourage, sending tokens is a good, budget-friendly option. From personalized robes to custom-label bottles of vino, there are many potential gifts that won't break the bank.

For larger bridal parties, it may be more financially sound to throw a group event like wine night at your place or a floral arrangement class (with a group discount).

This is an exciting experience to share with your friends, so don't forget to have fun. If you've always wanted to get your crew together for game night or a mani-pedi date, now is definitely the time to do it. You do want your bridesmaids to be both comfortable and interested in whatever creative proposal you concoct, so remember to take their interests and schedule into account. Book them weeks in advance if you have to and be flexible if they're more comfortable in a one-on-one setting. If you make them feel special and throw them a proposal to remember, they're sure to say "Yes!" to you. To ease the process, we tapped top wedding experts for their favorite bridesmaid proposal ideas.

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

01 of 30

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 to yourselves for the rest of the night.

02 of 30

Present a Picture Frame

You can't go wrong with a 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!"

03 of 30

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.

04 of 30

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."

05 of 30

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.

06 of 30

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 person who was asked to be a part of the wedding day. Bonus points if you can get each piece packaged in a jewelry box.

07 of 30

Meet for Afternoon Tea

Don your most feminine, floral print dresses as you and your favorites sit down for 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!

08 of 30

Begin 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. Whether you opt for a floral print, flannel, or a classic white terrycloth with monograms, one thing is for sure: Your crew will love the comfy gesture as much as they will adore being your nearest and dearest on the big day.

09 of 30

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.

Try to schedule your one-on-one proposals within the same week. You wouldn't want anyone to feel left out if their proposal comes a month later and all the other 'maids have already posted on social.

10 of 30

Say It With Vows

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."

11 of 30

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 the establishment has a private party room. You can also make it an 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.

12 of 30

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 stocking 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.

13 of 30

Send a Bouquet of Flowers

Another way to ask with flowers is to send your bridal party bouquets you think they'll love. Remember the thrill of receiving a bouquet of flowers? Do the same for your soon-to-be bridal crew and send handpicked arrangements to their home or office address. Make sure to ask where they prefer receiving a "package." Pop the "Will You Be My Bridesmaid?" question in the accompanying card.

14 of 30

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.

15 of 30

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!

16 of 30

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.

17 of 30

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!

18 of 30

Open a Box of Macarons

These sweet confections ooze feminine 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. She adds, “Food is always popular.”

19 of 30

Throw a Themed Movie Night

Gather your crew at your place for a night of popcorn, candy, and your wedding-themed film of choice. Opt for classics like 27 Dresses, Bridesmaids, or My Best Friend's Wedding. (You can even do a double-screening.) As the credits start rolling, say you have an important announcement. Pop the question by referencing a character or scene in the movie. A post-27 Dresses screening sample would be, "Will you be my Katherine Heigl?"

20 of 30

Host Game Night

Under the guise of a night of fun and games, invite your nearest and dearest and let them know prizes await. Prepare wedding-themed categories for games like Charades or Pictionary. Towards the end of the night, when you're about to announce your winners, hand out your "prizes" (aka bridesmaid proposal kits) to everyone. You can even say, "Everybody gets a prize because I'm hoping everyone will be on the same team: Team Bride."

21 of 30

Fill a Tote With All the Favorite Things

Sometimes it’s best to keep it cute and personal. Fill a cute 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.

22 of 30

Bake Them Cake

If you're a bride-to-be who loves to bake, why not make batches of your kitchen specialty. Whether it's cookies, cake, or pie, your friends will appreciate the love and effort you put into making the saccharine treat. Include a card with the big question or, if you're good at icing calligraphy, write down the question yourself in frosting.

23 of 30

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.

24 of 30

Host a Book Club

If you and your gal pals are avid readers (with book club experience), why not host a fake one? Choose a wedding-themed fiction book that you love, send out copies of the book to your friends, and tell them to meet with you over wine and cheese to discuss. (If they're not so keen on dissecting a book, tell them to just hang out anyway.) Facilitate the "session" with your proposal. You can reference the book, the characters, or just ask the classic, "Will you be my bridesmaids?"

25 of 30

Ask With a Luggage Tag

If you're planning a destination wedding, why not send out monogrammed luggage tags for your bridal party? Make the luggage tag read like a calling card with their name-comma-title (e.g., Lisa, Bridesmaid). On the accompanying note, write down, "Come on this journey with me?"

26 of 30

Surprise Them at Dinner

Tell your bridal dream team you want to get together for dinner to celebrate your engagement. Coordinate with the restaurant beforehand to do either one of two things, insert a card in each menu with the handwritten question. Or, even better, coordinate with a server to deliver small boxes (or envelopes) containing your note as they pour each guest a glass of vino.

27 of 30

Say It With Balloons

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.

28 of 30

Hand-Deliver a Pick-Me-Up

If you and your friends are big caffeine drinkers, why not meet them individually for lunch or in between work and hand-deliver a cup of their favorite coffee (or tea)? They will appreciate your pick-me-up delivery. As an extra present, order "Will You Be My Bridesmaid?" custom-label coffee packets and fill them with your favorite brew for a to-go treat your girls will love.

29 of 30

Register for Dance Class

Why not get the girls together for a night of salsa lessons? Book a private class just for your group. Towards the middle of the night make an announcement and say that you hope this will serve as "practice" for all the dancing they'll do as the bridesmaids at your wedding.

30 of 30

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.

FAQ

What should I put in my bridesmaid proposal box?

As a general rule of thumb: the more personal, the better. Whether it be a framed photo of the two of you, a monogrammed mug, or a bottle of their favorite bubbly, select items that you're confident your bridesmaids will use and enjoy.
How long after my proposal should I propose to my bridesmaids?

While everyone's timeline and situation is a bit different, it's usually best to propose to your bridesmaids a year to eight months before your wedding day no matter when your significant other popped the question.
What do I write in my bridesmaid proposal card?

Recognize the significance of your relationship and thank your bridesmaid-to-be for being such an integral person in your life. Most importantly, end the heartfelt note by popping the question: "Will you be my bridesmaid?"

How Many Bridesmaids Are Too Many Bridesmaids?