Bridesmaid Proposal Ideas: The Guide to Popping the Next Big Question

Getting engaged is such an exciting time in your life! You have some new bling, a new fiancé and you’re excited to share the news with your friends and family. But then comes the more difficult, but still exciting task of choosing your bridesmaids and asking them to be a part of your big day. To help make your life a little easier, we have plenty of bridesmaid proposal ideas and tips!

We’re going to break down the best advice for choosing your “I do crew,” and finding creative ways to pop the next biggest question to them. It’s all part of you wedding planning fun, so let’s dive in!

How to Choose Your Bridesmaids

There are probably many questions going through your head. How do you choose who to be part of the wedding? How many friends do you ask? What about family?

Before sharing any of your bridal party plans with your friends, or even thinking about invites, have a chat with your fiancé to decide how large you’d both like your bridal party to be and who you’d like to include. After all, you will be spending the rest of your lives together so it helps to be on the same page from the start.

While you may have some people in mind, you might also find yourself in a bind when it comes to who to ask and who not to ask so you don’t hurt anyone’s feelings. Take these scenarios for example:

I’ve been getting along really well with a coworker over the past year and we’ve really hit it off. Should I ask her?
My future husband’s best friend’s wife comes around often. Should I ask her?

You should never feel obligated to ask anyone to be in your bridal party, no matter who they are. After all, this is your day and it should be how you want it to be. If you think that coworker is a great friend and will remain that way, absolutely ask them! If you’re feeling a friendship kindle between you and your fiancé’s best friend’s wife, then ask her too. But don’t do it as a favor or because you feel bad.

Pro Tip: Think about the people who you know will be a friend of yours for life, and those who will be reliable and able to help you with your wedding details whenever you might need it.

When to Ask Your Bridesmaids

Don’t rush into handing them the invitation right away. Try waiting a few weeks to a couple months to plan your bridesmaid proposal invites. That way, you can give them as many details as you can about your day and what’s leading up to the moment you say “I do.”

Knowing your wedding date will allow your bridesmaids to get a better idea of whether or not they can commit to being your bridesmaid. The date might come at a bad time for them personally. Remember that being a part of a bridal party is a timely and costly responsibility that not everyone can commit to.

Pro Tip: Unless you’re on short notice, try to ask anywhere between a year and eight months before your wedding in order to give them enough time to get dresses and plan bachelorette festivities.

How to Ask Your Bridesmaids

Just like asking someone to marry you, there are thousands of ways you can ask “will you be my bridesmaid?”. You can ask your bridal party prospects in a group or one-on-one, and you can ask with a card, a gift, or treat. Here are 20 bridesmaid proposal ideas.

7 Tips on Bridesmaid Proposals

Don’t rush. Wait to ask until you have more details about your wedding day
Don’t ask someone just because they asked you
Give a small gift
Make it personal
Remind them of how much they mean to you
Spice it up! Not every proposal has to be the same
Be prepared that some may say no

20 Personalized Gift Ideas for Your Bridesmaid Proposals

You don’t need to give a gift, even a personalized note or card is enough. But if you are a gift giver, we’ve got you covered! Personalized gifts are a great way to remind those close to you how much they mean to you.

Childhood Friend: Fill a personalized box with cute gifts and lots of throwback pics that show your longtime friendship.

Wine Lover: Give her a personalized wine glass with her favorite wine!

Fitness Guru: Gift her a personalized water bottle or bridesmaid tank she can wear to the gym, and to your bachelorette.

Yogi: How about new personalized bridesmaid leggings, a sports bra, or grip socks? She’ll appreciate your thoughtful gift so much, she’ll have to say yes.

Ski Bunny: She would love a new hat or gloves she can use all winter!

Foodie: Gift her a food basket full of her favorite goodies! If she likes to cook, how about a new personalized bridesmaid apron so she can always remember your big day!

Party Queen: Throw together a gift box and fill it with champagne, shooters, and personalized shot glasses so she can celebrate your big moment.

Working Mom: Full-time jobs are stressful enough. Not to mention the job you can never quit, being a mom! Put together a de-stress gift box full of bath bombs, face masks, and a scented candle! You can even personalize the candle’s label to display your exciting message!

Shopaholic: How about a personalized gift bag they can take with them everywhere! Or set aside a day full of shopping so you can ask the question and create more memories to share.

Sister / Family Member: You know their favorites! Remind them of how much they mean to you with gifts that remind you of family.

Future Sister -In-Law: Welcome her into your circle with a meaningful gift that describes your friendship turned sisterhood.

College Roomie: Fill their gift box with memories from college to pop the question.

Sweetheart (and sweet tooth) Bestie: Bake them some treats to show them how sweet it would be if they stood by you on your big day

Coworker: Gift her a picture frame she can put on her desk!

Critical Thinker: Pop the question with a fun puzzle! They won’t even know what they’re getting themselves into.

Coffee Addict: She’d love a personalized coffee mug! Who doesn’t love a new mug? Make it a travel mug and she’ll never put it down.

Beach Babe: How about a personalized beach bag or towel? Depending on where your bachelorette or wedding is, she could surely use a cute bridesmaid bag or towel for the festivities!

Bookworm: Get them a new book, or a book on ‘how to be a bridesmaid’ for a good laugh. You can even ask them by writing your message in a bottle!

Movie Buff: Have a movie marathon and personalize your message on a popcorn package or one of their favorite candies.
Your Funniest Friend: Punny gifts are always great for a laugh!

Remember, not everyone’s gift has to be the same, and that’s the fun in personalized gifts! If you do want to send a more general gift box and proposal idea for your future bridesmaids, we have a couple ideas in mind.

Fill a gift box with more general and practical bridesmaid gifts like socks, a robe, and hair ties for the big day, and champagne to celebrate!
Ask them with a simple card! Not everyone is into giving and receiving big gifts. Ask the question in a simple card and tell them how much they mean to you!

Now You’re Ready to Pop the Questions

You see, there are so many ways you can ask “will you be my bridesmaid?” All your proposals can be fun and unique.

Remember to wait until you have more wedding details together before asking, so they know whether or not they can commit to the responsibility. And since there’s no rush, take the time and think about it so you can align your bridesmaid proposal ideas to each person you’re asking!