Planning a wedding — from setting up your registry to writing your vows to choosing your favors — should be one of the most special times in your life. Yet from the moment you agree to spend your lives together until the day you say “I do,” your to-do list can feel overwhelming — which is why you need to savor the moments that are fun and fill you with joy, love, and laughter.

Once you’ve decided where and when the festivities will take place, you need to decide who you want to be there with you. A bride should be surrounded by her very closest friends and family, the people in this world she loves most; thankfully, choosing these individuals is usually easy. Harder is figuring out how to ask your best friends, sisters, cousins, etc., to be in your wedding party.

So, we asked Jamie Mussolini, destination wedding planner and founder of Beachfronts Travel, to share some of the best bridesmaid proposal ideas. Whether your group is more traditional or goes for a more relaxed vibe, you’ll find a way to reach out to them in a thoughtful and memorable manner.

1. For the traditional women

Everyone loves to go out to dinner. For your special ask, plan a night out (your treat!) with your potential bridesmaids, and place a card at each setting. On the outside, write each person’s name and a note that they can find a surprise on the inside. When they open the card, it will reveal a message asking them to be in your wedding party. Once the business is out of the way, enjoy the evening of revelry!

2. For the ladies who lunch

As life gets busier and family schedules start overtaking weekends, your girlfriends will no doubt love to be invited to a shopping day at your favorite stores. Browse the dress section while discussing colors and styles to secretly learn what they prefer, and see if it lines up with your vision. Be open to ideas. Then at lunch, simply propose your question in person over prosecco or Champagne. Send them home with personalized to-do list notepads, and write on each one “Be Sally’s Bridesmaid!”

3. For the crew who likes to be pampered

Plan a spa day for your group: Everyone can get their preferred treatment and, afterward, you can pop the big question while you relax in hydrotherapy. Ahhhh. That mellow feeling won’t last long as the ladies will be over the moon with excitement for your big day. If you’re feeling generous, buy everyone a cute personalized kimono robe. They may wonder why you’re giving such a thoughtful gift — until they slip their hands in the pockets and pull out a note reading “Now that you’re relaxed and refreshed, will you be there to hold my dress?”

4. For those far away

Not all your bridesmaids necessarily live in close proximity. For your friends and family who live in another town or state (or country!), send flowers or cupcakes with a proposal note in the gift message. You may be separated by the distance between you two, but you will never feel closer to each other than when she calls you to say “I will!”

5. For the day of

It’s never too early to be prepared. Give your bridesmaids-to-be a gift box or personalized cosmetic bag of wedding day beauty essentials, such as makeup wipes, mini facial water sprays, perfume pens, and lip gloss. Pop in a proposal note for when they open the box or mini makeup bag.

MORE: 4 Must-haves in a Perfectly Personalized ‘Will You Be My Bridesmaid’ Box

6. For the bridesmaids supporting an older bride or a second wedding

Even if it’s your second go-around, or you’re simply arriving late to your party, celebrating your wedding day isn’t any less exciting or special. However, older brides or women getting married for a second time may simply want to set up a conference call, schedule an online meet, or send a group text asking if their friend will stand up with them on the big day. The answer is sure to be “Yes!” 

7. For the group that loves a Champagne toast

Hand out mini bottles of sparkling wine with a personalized “Will you be my bridesmaid?” label on them while getting pedicures together. Then, head home for a do-it-yourself sweets and sparkling wine bar to keep the party going with your raucous gang.

8. For brides who know their bridesmaids will accept

If you know your bridesmaid is a sure thing, give her a bangle, bracelet, or piece of jewelry you want her to wear for the big day. Make sure to also include a heartfelt note. This is a great gift to personalize with her name or initials, as it will serve as a generous memento of the exciting time in your lives you’ll never forget.

9. For the positive vibes girls

Maybe you have had a harder go of it in life but still managed to find your one true love. If that’s the case, send a lemonade cocktail kit or lemony mocktail concoction and add a note that reads “Life gave me lemons, but you helped make it lemonade. Will you do me the honor of being my bridesmaid?” Your happiness will shine through.

10. For the book club ladies

Create a book, photo book, journal, or scrapbook of memories, photographs, or stories, and add a note that reads “Will you do me the honor of helping me write the next chapter of my life?” It’s a tome they’ll turn to again and again as the years pass, laughing at the style of dresses you wore.

11. For the wine and cheese crew

If you have a group that loves aperitivo hour, invite them for an over-the-top cheese board and wine tasting. For their take-home gift, hand out bottles with a personalized label letting them know how much it would mean to you if they would join you at the altar on your big day.


Elizabeth Craig Wells is a former senior editor at Real Simple magazine where she focused on the Life, Style, and Simple Solutions sections. She writes for magazines, websites, and catalogs, and recently edited a 50-year history for an international women’s organization. Wells holds a B.A. in French and B.M. in flute performance from Northwestern University in Evanston, Illinois. She lives with her three children in Connecticut where she coaches soccer and tennis and is working on a series of contemporary novels.

Write A Comment