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Will You Be My Bridesmaid? 10 Creative Ways to Ask

by Bailey Gaddis
will you be my bridesmaid? proposal

While the proposal takes the cake for wedding question importance, the second most important proposal is asking the special ladies in your life to stand beside you as you pledge your love to your honey. Because asking, “Will you be my bridesmaid?” is so momentous, you might as well make the experience memorable. To help you out, we’ve collected some of the most creative ways to pop the bridesmaid question.

1. Surprise Party


Invite the besties you’d like as bridesmaids to a special location, and surprise them with your question. You can use a sign, have handwritten notes – with a gift – at their place settings, serenade them with a song that ends in the ask, or do anything else you’re drawn to.

2. Fortune Cookies


Have customized fortune cookies with your special question made, then pass them out at the end of a Chinese dinner (your treat, of course).

3. One-on-One Dates

If you want The Ask to be a more intimate endeavor, take each potential bridesmaid on a date to one of their favorite places. This one-on-one time will allow you to have a deeper conversation and take a trip down memory lane before you make your bridesmaid proposal.

4. Vows

Encourage your ladies to take on the bridesmaid role by writing and reciting customized vows to each of them. These vows can outline why you want them to be your bridesmaid while promising you’ll be a kind and chill bride-boss.

5. Gift Box


You can create a customized gift box for each bridesmaid with items you know they’ll love that can also be used for wedding events. Nail polish, perfume, jewelry, hangover pills (!) or any other goodies you think will jive with your ladies will likely be a hit.

6. Puzzle

If your nearest and dearest enjoy games, a puzzle with the big question printed on it can be a fun and surprising way to ask. But make sure to encourage them to finish the puzzle so the question doesn’t sit undiscovered in the back of a game closet.

7. Treasure Hunt

Ask your soon-to-be-bridesmaids’ inner child to come out by setting up a treasure hunt that ends with you popping the question. You can place objects, or cards with riddles, that provide hints about the location of the next clue at a fun outdoor space.

8. Monogrammed Jewelry


Have a piece of monogrammed jewelry made for each of your bridesmaids so they can remember this special union of bride and bridesmaid. You can have the same variety of jewelry made for all, or you can purchase unique items for each woman, depending on their style preferences.

9. Bottle of Wine

Since you can personalize most everything these days, why not personalize each woman’s favorite wine with a label that reads, “Will you be my bridesmaid?”

10. Scrapbook

Tap into your crafty side by creating a scrapbook for each of your bridesmaids that chronicles your friendship. Finish with a bang by creating a page that asks the ‘B’ question or features photos offering clues about what you’re asking.


More Bridesmaid Tips:

Who are the Bridesmaids / Honor Attendants?

How to Find Bridesmaids Dresses For All Body Types

How to Give Bridesmaid Gifts When You’re an Adult

How to Pick Your Wedding Party

Your No-Stress Guide to Bridesmaid Dresses

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