How to Propose to Your Bridesmaids | Bridesmaid Proposal

First, deciding how to propose to your bridesmaids can be one of the most important and exciting parts of planning your wedding! After all, these are the ladies who will be cheering you on from the engagement all the way into your marriage. Luckily, there are so many different bridesmaid proposal ideas out there to help you ask your best gals and celebrate those who will stand beside you on your big day. 

So just where do you begin when proposing to your future bridesmaids? Believe it or not, there are a several things to think through when figuring out how to pop the second biggest question. A bridesmaid proposal can be personalized specifically to each of your favorite ladies, or you can do the same thing for everyone. You can ask them all at once by throwing a party, or ask each of them individually, for instance. Keep reading for helpful ideas of where to begin no matter what kind of proposal you're hoping to do. Either way, just have fun and don't be afraid to get creative with this part of your wedding planning process!

1. Brunch Proposal Party
2. Personalized Wine Bottle
3. Bridesmaids Hair Ties
4. Bridesmaids Box with Brumate*
5. Bridesmaid Jacket
6. Bridesmaid Puzzle
7. Tying the Knot Jewelry
8. Bridesmaid Box with Pajamas*
9. Champagne Gummies
10. Proposal Cookies

1. Brunch Proposal Party

Above all, there's no better way to ask all your best gal pals to stand beside you on your wedding day than throwing a bridesmaids proposal brunch? First, Invite everyone over for everyone's favorite breakfast foods and celebrate the beginning of wedding planning season together. Next, you can ask your girls using wine tumblers like the bridesmaids ones from Simple & Sentimental, and once you have those out you may as well make mimosas to put in them! What a fun way to gather your bridal party for the first time and celebrate as a group.

2. Personalized Wine Bottle

Don't have time to throw a brunch bash? No worries! Luckily, you can opt for these personalized "Will You Be My Bridesmaid?" wine bottle bridesmaid proposal labels instead from Amazon. Find the right ones for all your ladies, whether bridesmaid, maid of honor or matron of honor. They are easy to apply to any of bottle of your favorite wine and such a simple way to propose to your bridesmaids. And who doesn't love a bottle of wine, what a great gift that keeps on giving!

3. Bridesmaid Hair Ties

Pun definitely intended. These bridesmaid proposal hair ties from Amazon can be the perfect way to ask your ladies! With their arrangement of different colors and patterns you'll surely be able to find some for each of your soon-to-be bridesmaids. Moreover, we all know we can never have enough hair ties!

4. Bridesmaid Box with Brumate

These pre-made bridesmaid proposal gift boxes from Simple & Sentimental come with custom Brumates. Brumates are the best insulated tumbler to keep your cans and drinks in and will keep them cold for hours. You can choose between getting your friends names printed on them or their role in the wedding and Simple & Sentimental will even package them for you in these personalized bridesmaid proposal boxes. Also, perfect that they could then use them for all coming wedding festivities as well! Therefore, you don't want to miss out on these.

5. Bridesmaid Jacket

First off, how CUTE are these personalized bridesmaid jean jackets from RoseGoldRebel on Etsy? There can't be a more stylish way to propose to your girls. After all, about how cute the wedding pictures will be with the party showing off these on top of their dresses! 

6. Bridesmaid Puzzle

Simple & Sentimental has so many creative personalized gifts but these bridesmaid proposal puzzles might be a favorite. For instance, think about how fun it will be for your girls to have to put the gift together to see the message! These are totally customizable with any photos and come in several sizes. 

7. Tying the Knot Jewelry

These "Tying the Knot" bridesmaid proposal bracelets from HundredHearts on Etsy are to die for. What a classy way to pop the question! In addition, you'll also already be a step ahead on finding their wedding day jewelry, which will be a life saver with all the decisions you'll be making in the coming months.

8. Bridesmaids Box with Pajamas

This fall-themed bridesmaid box from Simple & Sentimental comes complete with personalized pajamas and a candle.  Secondly, you can also customize and add on  different items to the box as well. What a sweet way to ask your ladies to stand by your side and also gift them a cozy set to start their next spa night off right! 

9. Champagne Gummies

For starters, who doesn't love candy?! These Champagne + Prosecco Gummy bottles from Simple & Sentimental are to die for when it comes to bridesmaid proposal ideas. They taste exactly like your favorite drinks and are the perfect asset to proposing to your life-long ladies!

10. Proposal Cookies

These may be the most beautiful bridesmaid proposal cookies ever. RojosBakery from Etsy will hand make each of these to send or for you to personally deliver to each of the girls. You can even get one to look like a wine bottle!

Friends Forever

There will be so many decisions for you to make during your wedding planning season. That's why starting out with figuring out your bridesmaid proposal is one of the most important first steps to take after getting engaged. These are the girls who have and will continue to stand beside you through thick-and-thin and what a personal way to celebrate them than asking them to stand by your side as you say your I Do's. You can't go wrong with any of these top ten ideas! Happy proposing!

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We share blog posts with personalized gift ideas and inspiration every week at simplesentimental.com. Submit blog post topic requests by emailing us at hello@simplesentimental.com or contacting us!