10 Creative Ways to Pop the Question

You’re engaged! Time to start planning the big day, right? Not so fast. Now that you’ve said yes to the happily-ever-after, it’s time to pop the question yourself and ask sisters, friends, extended family, or coworkers to be your bridesmaids in your wedding. Rather than sending the chosen ones a mass email between contacting potential caterers, why not get a little creative with the time-honored question?

10 Ways to Ask “Will You Be My Bridesmaid?”

1. Customized Wine Bottles

One festive way to gather your girls is to propose a group wine tasting or night at your home. Wait 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 bridesmaids for the big day. Needless to say, you’ll be toasting yourselves the rest of the night.

2. Surprising Fortune Cookies

Keep food and beverages in mind when it comes to asking pals to serve as bridesmaids: “Invite the gang over on the pretense of enjoying some takeout Chinese food and a movie. 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.”

3. Bling for Your Besties

Stage a bridesmaids’ luncheon that celebrates the bride-to-be’s true “gems” in her life. The gemstone theme naturally lends 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.

4. Coffee Dates

Can’t get the squad together all at once? Don’t fret. We suggest organizing a special day with each woman and meeting her for a to-go coffee first, saying: “Ask the barista to write the question on the cup—instead of your friend’s name—as a surprise.” Just make sure your pal reads it before she drains her java!

5. Thoughtful Gift Boxes

If quirky or nontraditional gestures aren’t your thing, a simple gift box filled with wedding-related items is usually a safe bet. Pick out a bottle of pretty nail polish (perhaps to match your wedding color scheme if you have one), a mini bottle of bubbly, and simple jewelry or thoughtful hand-made soaps to go along with a sweet handwritten note. Let them know how much they mean to you, reflect on the best memories you’ve shared together, and why you absolutely have to have them in your wedding party.

6. Sweet Picture Frames

You can’t go wrong with photo of you and your future bridesmaid in a custom frame asking her to be your bridesmaid. It’s something she can treasure forever, and it commemorates the momentous occasion. The photo can either be of just you and her or, if you and your bride tribe are already all friends with one another, it can be a group photo. Whatever you choose, she’s sure to love it and say “Yes!”

7. Get Creative With Balloons

“Give your girls a little box, each with a small inflated balloon and a safety pin inside. When they pop the balloon, they’ll find a message that says ‘Now it’s time for me to pop the question! Will you be my bridesmaid?'” says Meaghan Hurn, the creative visionary behind Hurn Events Management. You can also add confetti or glitter to the inside of the balloon for an added bonus. Tip: Don’t mail these, they deflate along the way!

8. Scratch-Off Card

For a fun twist, 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?” Pair the card with nail polish and a pair of gorgeous earrings in your wedding colors, and your bridesmaid can wear them on the big day!

9. Vow Not to Be a Bridezilla

Here’s a fun idea, “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. Call out the fact that if you do turn into a bridezilla, you’re hoping they snap you back into place like they have done time and time again throughout the last couple of years.”

10. Write a Sweet Note in a Funny Book

If you’re wondering how to ask bridesmaids to be in your wedding in a funny way, we have an idea for you. “If you have a sense of humor, gifting your gals 101 Uses for a Bridesmaid Dress (with a personal note inscribed inside!) is a tongue-in-cheek way of making the ask,” she says.

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