Fun Ways to "Propose" to Bridesmaids in 2021

These creative bridesmaid proposals are sure to end in a yes!

By: Jen Glantz

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The Perfect Bridesmaid Proposal

Asking your closest friends and family to take on the special role of bridesmaid for your wedding is a moment you’ll always remember. So, how do you pop the question to your bridesmaid squad in a way so special, it’ll leave them feeling all gooey inside? How about a proposal that shows them appreciation before they dive in and take on all of their bridesmaid duties?

If you’re looking for fun ways to propose to your bridesmaids this year (especially the ones that live far away or the ones you might not be able to see in person because of the pandemic), here’s a handful of ways to ask them that’ll end with a gigantic yes!

Send Them a Curated Box

Each of your bridesmaids have different personalities, hobbies, and overall charms to them. Put together a curated box for each bridesmaid with handpicked items that you think they’ll adore. Consider including monogrammed pieces with their initials, using their favorite colors, or choosing their favorite sweet treats. Inside the box, write a personalized note to them asking if they’ll be your bridesmaid.

Host a Virtual Wine Night With Each One

When you thought about your ideal bridesmaid proposal, perhaps it involved taking each person out to a wine night or happy hour event to ask this question. If that’s no longer possible, try hosting a wine night video chat with all of your friends or family members to catch up. Then, ask them to raise their glasses as you propose the question during your virtual celebration.

Plan a Virtual Hang Out With a Surprise Guest

Some of the best bridesmaid proposals happen when the bride brings all her soon-to-be bridesmaids together and asks them at the same time. Consider playing into this virtual world by hosting a video call where you invite a special guest to add fun to the experience. Perhaps it’s a magician, a comedian, or a palm reader. This an activity and bridesmaid proposal in one!

Scratch-Off & Lottery Cards

It can truly make a person feel lucky when the bridesmaid question is popped! Have fun with your proposal by sending a scratch-off card that asks the recipient to be your bridesmaid. Be sure to include some real scratch-offs too. Who knows? Maybe one of your bridesmaids will win big!

Send a Bridesmaid Proposal Puzzle

The go-to trend of the pandemic, doing living room puzzles, can certainly come into play here. Consider sending out personalized bridesmaid proposal puzzles for each person. Make the puzzle pieces come together to create a picture of the two of you and the big question as well.

Do a Celebrity Shout-Out

Why not add a celebrity twist to the proposal process? Tap into celebrity video websites, like Cameo, to pick each bridesmaid’s favorite celebrity and pay to get them to create a personalized video asking the question for you. This will truly be the gift that keeps on giving.

Put Together a Self-Care Kit

Since most of your bridesmaids are spending more time at home than ever, put together a self-care kit so they can find some extra relaxation during their bridesmaid adventures. Inside the kit, add face masks, candles, bath salts, and a personalized note popping the question to them.

Keep the Proposal Going With a Subscription Box

If your bridal party is scattered all over and there won’t be many chances for the group to get together in person before the wedding, you can ask your bridesmaids the coveted question with a special box that keeps the treats coming monthly. A subscription box is an amazing option! Whether it’s a wine, beauty, food, or decor-themed box, these subscriptions will give your bridal party something to be excited about every single month.

Fun Ways to "Propose" to Bridesmaids in 2021

Related To:

Shop This Look

The Perfect Bridesmaid Proposal

Send Them a Curated Box

Host a Virtual Wine Night With Each One

Plan a Virtual Hang Out With a Surprise Guest

Scratch-Off & Lottery Cards

Send a Bridesmaid Proposal Puzzle

Do a Celebrity Shout-Out

Put Together a Self-Care Kit

Keep the Proposal Going With a Subscription Box

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