If you are ready to embark on the journey of a lifetime with your besties by your side, then it is time to pop the question and ask your favorite girls to be your bridesmaids. Also, do not settle for the boring old "Will you be my bridesmaid?" ideas. From thoughtful keepsakes to playful surprises, we have curated a list of creative bridesmaid proposal ideas that will leave your soon-to-be bridesmaids swooning. Please Scroll down to discover our top bridesmaid proposal box ideas and make your bridal party proposal memorable.

Bridesmaid Proposal Scavenger Hunt

A bridesmaid proposal scavenger hunt is a unique bridesmaid proposal idea. It is a perfect way to ask your bridesmaids to stand by your side on your special day. Start the hunt by sending each bridesmaid on a mission to find hidden clues that will lead them to the final destination. Along the way, each bridesmaid will discover clues to the big question “Will you be my bridesmaid?”

Bridesmaid Proposal Survival Kit 

A bridesmaid proposal survival kit will come in handy during the wedding planning process. Put together a personalized engagement gift box for each bridesmaid that includes items like a mini bottle of champagne, lip balm, nail polish, and a personalized note of appreciation. Your bridesmaids will love the thoughtfulness of this bridesmaid proposal box, and it will be a lasting reminder of your special day.

Spa Day 

Put together a personalized spa day package for each bridesmaid. This package should include pampering items like bath bombs, massage oils, and face masks. Also, they can relax and enjoy a day of pampering while they anticipate your big day. A spa day is one of the best bridesmaid proposal gifts for your luxury girlfriends. 

Bridesmaid Proposal Personalized Cooking Class 

If your bridesmaids are foodies and love to cook, take them to a cooking class and learn to make a special dish together. A bridesmaid proposal personalized cooking class is one of the unique "asking bridesmaids gifts". It can be a fun activity that your bridesmaids will enjoy and remember. 

Bridesmaid Proposal Personalized Adventure

Depending on your budget and bridesmaids’ interests, you can plan a hot air balloon ride, a weekend getaway, or even a skydiving experience. These "will you be my bridesmaid gifts" will remind them of all the fun times you have had together. At the end of the adventure, surprise your bridesmaids with the big question.

Bridesmaid Proposal Customized Board Game 

Customized board games are a fun and creative way to ask your bridesmaids to be part of your wedding day. Create a personalized board game that your bridesmaids can play. Also, the game can be tailored to match the theme of your wedding. This is one of the fun bridesmaid proposal gift ideas.

Bridesmaid Proposal Personalized Phone Case 

Have a custom phone case made for each of your bridesmaids with their name or initials. This phone case can also include a photo of the two of you or have a special message. Also, this unique bridesmaid proposal gift can be a design that your bridesmaids adore. 

Fortune Cookies 

In case you do not know what to put in a bridesmaid proposal box, fortune cookies are a great idea. You can buy custom-made fortune cookies online with your special question inside. The message can either ask your bridesmaids directly to be part of your wedding day, or it can be a funny or heartfelt message that will remind your bridesmaids of all the fun times you have had together. 

Scratch-Off Card 

Make a unique card that has a scratch-off area. Include a cent for scratching in the envelope. Under the scratch-off part of the card, your friends will find a message for them. This is one of the creative “Will You Be My Bridesmaid Gifts” to give your girls.

Stemless Wine Tumblers 

We love the recent trend of stemless wine tumblers. They are a thoughtful gift for your girls who love to enjoy some wine. These personalized bridesmaids' proposal ideas are a perfect gift for your bridesmaid.

Personalized Flasks 

Give your bridesmaids personalized flasks for your wedding day. The flasks can be engraved with their initials or a special message. They will love having a personalized flask to bring along on your special day. This is one of the best "will you be my bridesmaid gifts".

Custom Embroidered Robes 

Custom embroidered robes are one of the luxurious "asking bridesmaids gifts". Give your bridesmaids custom-made robes with their initials written on them. They will love being able to get ready in their personalized robes on the morning of your wedding.


Bridesmaid proposals are an exciting part of wedding planning and are a great way to show your bridesmaids how much they mean to you. From personalized gifts to creative activities, there are endless ideas to choose from. When coming up with bridesmaid proposal ideas, think about your bridesmaids’ personalities and interests, and find something that will make them feel special.