Congratulations, you’re engaged! Now that you’ve said “yes” to your forever partner, it’s time to pop another important question to your closest friends and family—“Will you be in my wedding party?”

This is a special moment for you and your wedding crew, so why not make it memorable and fun? Whether you’re asking your maid of honor, best man, or the rest of your bridal party or groomsmen, here are some unique and playful ways to ask them to stand by your side on the big day.

1. Personalized Gift Boxes

Who doesn’t love a box full of surprises? Put together a small gift box with thoughtful and creative items related to the wedding. Here are a few ideas to include:

• For the Bridesmaids: A mini champagne bottle, a personalized candle, or a cute pair of earrings.
• For the Groomsmen: A custom flask, socks, or a bottle opener engraved with their name.
• The Final Touch: Add a handwritten note or card that says, “I can’t say ‘I Do’ without you. Will you be my [role]?”

This makes for a thoughtful keepsake and sets the tone for all the excitement ahead.

2. Create a Puzzle

Turn the question into a fun challenge by creating a custom puzzle. You can have a puzzle designed with the question “Will you be my [role]?” and give it to your friends to solve. Not only is this a creative way to pop the question, but it also doubles as a fun bonding moment.

3. A Themed Dinner Party

Gather your favorite people for a dinner party, themed to the question you’re about to ask! Incorporate decorations, food, or even desserts that hint at the occasion. For instance:

• Custom napkins with “Will You Be My Bridesmaids/Groomsmen?” printed on them.
• A dessert reveal—cupcakes or a cake with the big question spelled out inside.

At the end of the night, have a toast to announce your wedding party officially.

4. Scratch-Off Cards

Give your friends a little mystery with custom scratch-off cards. They’ll have to scratch an area off to reveal the hidden message asking them to join your wedding party. It’s simple, affordable, and adds a playful twist to the moment.

5. Custom Clothing or Accessories

Surprise your wedding party with something they can wear! Think:

• Shirts that say, “Maid of Honor,” “Bridesmaid,” or “Groomsman.”
• Hats or socks that include their new title.

Wrap it up and watch their faces light up as they unwrap their role for the big day.

6. Plan a Fun Outing

Treat your friends or family to a fun outing where you ask the question. Some ideas include:

• A wine tasting tour where you present a custom wine bottle labeled with “Will you be in my wedding?”
• A group escape room with the question worked into the clues or solved as part of the puzzle.
• A casual picnic or gathering at a park topped off with a heartfelt proposal to your wedding party.

The outing itself becomes part of the memory, making the moment extra meaningful.

7. Custom Video Message

If some of your wedding party lives far away, you can still make it special with a custom video. Record yourself (or even get creative with animations or a slideshow) asking them if they’ll be part of your big day. Include personal touches like photos or memories to make it even more heartwarming.

8. Engraved Keepsakes

A classic and sentimental approach is gifting them a personalized keepsake engraved with the question. Popular options include:

• Bracelets or necklaces for bridesmaids.
• Cufflinks or pocket watches for groomsmen.

It’s a special way to make them feel appreciated and excited for the role ahead.

9. Surprise with a Balloon Reveal

This idea is equal parts colorful and fun. Place a balloon in a box that says, “Pop me!” Inside, include paper confetti and a note revealing the question. It’s an easy yet festive way to take the moment up a notch.

10. Photo Memories

Craft a mini photo album or frame filled with pictures of you with your future bridesmaid or groomsman. At the end of the album or frame, leave a note asking them to stand by your side. It’s a sweet and sentimental way to reminisce while looking forward to making more memories together.

However you choose to ask, remember the gesture is as important as the message. These are your people—the ones who’ve been there for you through thick and thin. Whether you go big and extravagant or keep it sweet and simple, make the moment meaningful.

Good luck, and enjoy this exciting part of the wedding planning process! If you have other fun or creative ideas, share them in the comments—we’d love to hear.