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5 Unique Bridesmaid Proposal Ideas

By Kate Cohen

Ask your besties to stand by your side with a unique bridesmaid proposal.

Congratulations – you’re engaged!

Now it’s time to assemble your “I Do Crew.”

While you may have gotten the first proposal, it’s time to pop the question to your closest friends and family: “Will you be my bridesmaid?”

These days, the trend of elaborate bridesmaid proposals has emphasized the importance of this question more than ever.

It’s not uncommon to propose to your bridal party members-to-be with personalized pajamas, monogrammed wine glasses, and other trendy gifts. But while these things look beautiful when presented, they’re often not the most practical and can end up unused in the back of a closet or cupboard.

Instead, consider proposing with something a little more personal (and often more cost-effective). Your bridal party members-to-be will appreciate the thought and not having to find space for a new mug that says “bridesmaid.”

Here are 5 unique bridesmaid proposal ideas that we love.

Note: The word “bridesmaid” tends to be associated with female-identifying individuals, but these days, your bridal party can be made up of whomever you choose to stand by your side as you say, “I do.”

For the purposes of this blog, the term “bridesmaid” is used frequently, but refers to anyone, female, male, or non-binary, that you choose to be a part of your bridal party.

5 Unique Bridesmaid Proposal Ideas

A Gorgeous Bouquet of Flowers

Sending a beautiful floral arrangement is a great bridesmaid proposal idea.

Nothing brightens your day quite like getting a stunning bouquet of flowers. Sending your besties an arrangement makes a big, beautiful impact that will undeniably bring a smile to their face.

This is a great option if you have bridesmaids all over the country, though you can always hand-deliver the flowers yourself to anyone who lives nearby. Do a little research and find some fabulous local florists that can create and deliver a spectacular floral display.

Accompany the arrangement with a heartfelt card that pops the question. You can guarantee that even if you can’t ask them to be in your bridal party in person, it will still be a bridesmaid proposal they’ll never forget.

Sugar Cookies

A beautifully decorated cookie is a great idea for a bridesmaid proposal.

Beautifully decorated sugar cookies are a trend that look as amazing as they taste. A customized cookie decorated to say, “Would you be my bridesmaid?” is a lovely way to ask someone to be a part of your big day.

Plus, a delicious cookie will never sit around and create clutter. Let’s face it, it’s going to be swiftly eaten. It’s arguably one of the more delicious bridesmaid proposal options.

Many cities have bakeries and independent artists dedicated to the fine art of cookie decorating. If you’re not sure where to start, there are plenty of Etsy shops that will customize and decorate a cookie (or set of cookies) to suit your vision.

These beautiful cookies also ship well, so it’s easy to get them to your bridal-party-to-be, wherever they live.

Quality Time

Another unique bridesmaid proposal idea is simply spending quality time together. 

It’s getting harder to find the time to connect with our friends and loved ones due to crazy busy schedules. One of the best ways to ask your bestie to be in your bridal party is to ask them in person while spending quality time with them.

Maybe you treat them to a mani/pedi or buy them a drink at happy hour after work one day. Or meet for a walk around the park for some quality catch-up time. You’ll both love the good company, and you can have the honor of asking them to be a part of your big day in person.

Contribute to Their Wedding Costs

Being a bridesmaid isn’t cheap. Between the bachelorette party, the dress, the hair and makeup, and potential travel expenses, there’s a lot of money that goes into being in a bridal party.

One of the ways you can acknowledge the weight of the question you’re asking is by contributing to their wedding expenses as part of your bridesmaid proposal.

Instead of spending money on things that will end up gathering dust in a cupboard, use it on a gift card to the boutique where you plan to choose their bridal party outfits. It may not cover the entire ensemble, but every little bit helps.

Offer to pay for their hair or makeup on the big day. Contribute to a hotel room if you’re planning a destination wedding. Again, it doesn’t have to be a major financial gift, but something to show that you understand and appreciate the money you’re essentially asking them to spend can be meaningful.

A Trip Down Memory Lane

One unique bridesmaid proposal idea is sharing photos and memories that emphasize the importance of your relationship.

Your bridal party is an array of people who have known and loved you through many different walks of life. There’s no better way to show them how much they mean to you than by putting together a collection of personal memories you share with that person.

A small album of photos, a memory box of trinkets, or even a handwritten letter can mean the most when it comes to family and friends.

You can even try to recreate one of your favorite memories or an element of a memory that is special to you.

For example, if your favorite memory with your bestie is of the two of you sipping Aperol Spritzes while backpacking through Europe, make an Aperol Spritz at home and toast to that special moment that means the most to you.

Or, if you and your sister used to spend hours drawing in the driveway with sidewalk chalk as kids, meet her somewhere outside with a bucket of chalk and take a moment to revisit your childhood. Writing “Will you be my bridesmaid” on the pavement in chalk could be the perfect way to pop the question.

When it comes to incorporating memories into your bridesmaid proposal, the possibilities are endless.

Keep in Mind

Make it Personal

Presumably, the people you’re asking to be in your bridal party are some of the people you know best in the world. While a beautifully prepared box of goodies may look picture-perfect, it can sometimes risk feeling impersonal depending on the person to whom you’re gifting it.

For example, the idea of a personalized wine tumbler and a mini bottle of prosecco could be a great fit for one friend but seem thoughtless to someone who you know doesn’t drink alcohol. Even the most beautifully decorated cookies could be considered in poor taste when gifted to someone who can’t eat gluten.

If you’re planning on putting together a bridesmaid proposal with a gift, make sure your favorite people feel special by giving them something that shows you know and appreciate them as individuals.

You Don’t Have to Go Big

The question “Will you be my bridesmaid?” is a big deal in and of itself; how you ask the question doesn’t have to be. Don’t feel pressured to go above and beyond with a big gift or a flashy surprise for your bridesmaid proposal. These are the people who know you best. Hopefully, they’re honored just to be asked, with or without a gift.

They’re Allowed to Say “No”

Something else to keep in mind: over-the-top bridesmaid proposals can put a lot of pressure on someone to say “yes.”

Being a bridesmaid is a big responsibility that requires hefty time and financial commitments. If someone isn’t in the right place to commit to being in your bridal party, it can be really hard to say so, and even more uncomfortable having just opened an elaborate, personalized gift.

Understanding that “no” is an acceptable option leaves room for those who aren’t completely committed to accepting your proposal. If someone says no, let them know it’s ok. They should still be invited to your wedding.

You Do You!

That being said, it’s your wedding! If you’ve been dreaming about the moment of asking your besties to be your bridesmaids with customized pajamas and wine glasses, go for it! The bridesmaid proposal sentiment is still thoughtful and will be appreciated.

Let Rosen Weddings Be Your Next Proposal

Now it’s our turn to propose.

Will you be a Rosen Weddings couple?

We would be honored to have you visit one of our four elegant wedding venues to see which one best suits your vision for your dream wedding. We’ll impress you with decadent catering packages, generous room discounts for your guests, and amazing amenities to make your wedding day unique to you.

Contact us today to set up a time to chat with our incredible weddings team. We can’t wait to hear from you!

We Bring Your Dream Day to Life.

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