100 Will You Be My Bridesmaid Proposal Ideas (2024)

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Are you looking for the best “Will you be my bridesmaid” proposal ideas? We have put together this ultimate guide to help you with the process.

Asking someone to be your bridesmaid or maid of honor is one of the most important things that you will do during the beginning of your wedding planning journey. These are the people that are going to be by your side throughout the entire process.

Here is what we will cover in this article:

A bride and her bridesmaids laughing. This is for the article called will you be my bridesmaid proposal ideas.
Choosing your bridesmaids is one of the first things to do when wedding planning

Creative Ideas For Doing A Bridesmaid Proposal (Fun and Unique Ways To Ask Your Girls)

If you are looking for a few creative, unique, or fun bridesmaid proposal ideas, here are a few to get you started:

1. Host a wine party

If you and your girls are wine lovers, this is a really fun idea. Invite them over for wine tasting and dinner, and then have them all open a gift bag that includes a wine bottle with a custom “Will you be my bridesmaid” label. We have included a few options later in the article.

2. Have them over for brunch

Treat the girls to Sunday brunch and gift them a mini champagne bottle with a custom “Will you be my bridesmaid” label on it. Then make mimosas and enjoy some amazing food.

3. Take them out to coffee

Invite your girls out for a coffee date and surprise them with a custom “Will you be my bridesmaid” coffee/travel mug. We posted photos and a link to a really awesome Etsy store that makes them later in this article.

4. Go out dancing (or a retro skate night)

Plan a night out dancing with your girls or head to the local skating rink and have the DJ make an announcement. This is a super creative way to “pop the question” to your girls.

The DJ can say something like:

May I please have your attention. We have a special girl in the house tonight with some very special friends. This is a message to all of the friends with (bride’s name), she was wondering if you would be her bridesmaid!”

5. Make each bridesmaid a memory box

This is a really sweet idea that your girls will definitely cherish. Make each bridesmaid a box with memories of the two of you together. And since you probably have girls from different times of your life, this will be a very unique gift to each girl.

Some of the things that you can include are:

  • Photos
  • a small photo book
  • A slideshow (video or photos)
  • A scrapbook with memories that you shared together (concerts, school, work, etc.)

6. Ask them with a proposal box

This can be a box that includes personalized items that you want them to wear on the wedding day (robes, PJs, slippers, jewelry, etc.), or it can be things that you/they love (drinks, food, makeup, phone case, succulents, etc.).

We have a ton of ideas down below with photos and links. Some of the items below include cookies, jewelry, proposal boxes, sleepwear, robes, greeting cards, travel mugs, wine glasses, dress hangers, and more!

Do You Give A Gift To The Bridesmaids When Asking Them To Be A Bridesmaid? What Do You Give Them?

You do not have to give a gift when asking your friends or family to be your bridesmaids, but it’s nice to give them a little something, even if it’s just a card or letter.

If you do plan on giving them something when you ask them to be your bridesmaid, this would be the perfect time to get them robes or pajamas for the wedding morning, slippers, shirts for the bachelorette party, bags with their name, glasses to drink out of at the wedding, etc.

Anything that you want the bridesmaids to use or wear for/on your wedding day should be given as an extra gift (or for the bridesmaid proposal). This should not be a gift to thank them for helping you with the wedding. As mentioned before, if you want to save money, a simple card or letter would be very appreciated by your bridal party.

You can also give them a more personal gift closer to the wedding (bachelorette party, rehearsal dinner, the morning of the wedding, etc.). This can be something that they can actually use after the wedding day. Here are a bunch of ideas: (Article coming late Feb.)

If you are looking for bridesmaid proposal gifts, we have a bunch of ideas below.

A bride and bridesmaids wearing pink floral matching robes. This is for the article called will you be my bridesmaid proposal ideas.
Matching robes for the wedding day morning make great “Will you be my bridesmaid?” proposal gifts.

Personalized Will You Be My Bridesmaid Proposal Gift Ideas

There are so many amazing proposal gift ideas to give your bridesmaids, maid of honor, or matron of honor. We have picked out a few of our favorites from the best shops on Etsy.

When personalizing your items, you can just do names, or you can add things like “bridesmaid” or “maid of honor“. Or you can simply leave off all personalization and purchase the items just plain.

Will you be my bridesmaid proposal boxes (complete and put together)

Here are a few beautiful “Will you be my bridesmaid?” proposal gift box ideas. These are complete packs that are already put together for you.

We love these bridesmaid proposal boxes from SincerelyMeGift on Etsy:

A will you be my bridesmaid proposal box gift. This is three different color options.
So many different styles of proposal boxes available

We absolutely love these beautiful “Will you be my bridesmaid?” proposal gift boxes from ModParty on Etsy.

A few bridesmaid proposal gixt boxes sitting on a table.
We love the look of these bridesmaid proposal gift boxes

And these gorgeous proposal gift boxes from LoveLinax on Etsy.

A collection of gift boxes on a table. This is for the article called best will you be my bridesmaid proposal gift ideas.
These bridesmaid proposal gift boxes are so perfect!

Check out these beautiful proposal boxes from PaolaBrownShop on Etsy.

two bridesmaid proposal boxes sitting on a table.
So many styles and colors to choose from

Will you be my bridesmaid wine bottle labels and mini champagne bottle labels

Adding a custom “Will you be my bridesmaid?” label to a wine bottle or champagne bottle is a very simple gift idea to give your bridesmaids, maid of honor, or matron of honor.

We love these wine bottle labels from LifesMemorableEvents on Etsy.

Custom wine labels that say will you be my bridesmaid on them.
A classy way to ask your friends and family to be your bridesmaid

These custom wine bottle labels from ThePrettyLittleMess on Etsy are so awesome!

three wine bottle labels on a table that say will you be bridesmaid, will you be my maid of honor, and will you be my matron of honor
We love the modern look of these custom wine labels

We also love these bridesmaid proposal wine labels from LabelWithLove on Etsy.

A collage of photos that feature custom wine bottle labes that say will you be my bridesmaid on them
A wine bottle label is a fun way to “propose” to your bridesmaids, maid of honor, or matron of honor

Many more “Will you be my bridesmaid?” wine bottle label ideas here on Etsy.

Will you be my bridesmaid, maid of honor, or matron of honor macarons

These designer macarons by LeilaLoveMacarons on Etsy are such a fun and unique way to ask your bridesmaids, maid of honor or matron of honor to be a part of your special day.

A photo of pink macarons that say will you be my bridesmaid on them. Another set says will you be my maid of honor
How fun is this bridesmaid proposal idea!?

Will you be my bridesmaid cookies

I mean c’mon, is there really a better way to ask someone to be your bridesmaid than with a cookie? We don’t think so either.

We love these “Will you be my bridesmaid?” cookies made by CookieDeauxCreations on Etsy.

A bunch of custom cookies that say will you be my bridesmaid on them.
These custom “Will you be my bridesmaid?” cookies are amazing! Calendar/wedding date, dress, personalized with names. Whatever you can think of, they can do it!

We love these bridesmaid proposal cookies by OneSweetGift on Etsy.

custom made cookies that say will you be my bridesmaid
Adorable cookies for bridesmaids, maid of honor, and matron of honor.

For even more bridesmaid proposal cookie ideas, check them out here on Etsy.

Will you be my bridesmaid scratch off card

These scratch-off “Will you be my bridesmaid” cards from XOXOKristen on Etsy are such a fun and unique idea.

A will you be my bridesmaid scratch off card. with a big gold heart in the middle of card
Scratch off “Will you be my bridesmaid?” cards are a fun and unique proposal idea

Bridesmaid and Maid of Honor proposal cards

If you are looking for the perfect bridesmaid card, we have so many great options for you to check out.

Here are a few “Will you be my bridesmaid?” cards that we love:

 a will you be my bridesmaid card sitting on a table
Handmade and sold by Luckynotes on Etsy
A torn paper style bridesmaid proposal card on a table
Handmade and sold by Littlecarabaostudio on Etsy
A photo card that says will you be my bridesmaid
Handmade and sold by TheSunshineGarden on Etsy
cartoon drawing of a bride and bridesmaid on a proposal card
Customize the skin color, dress, and hairstyle (Handmade and sold by FoxesOnBoxes on Etsy)

*Check out these other bridesmaid proposal cards on Etsy.

DIY Bridesmaid Proposal (Homemade Ideas)

If you want to customize your bridesmaid proposal gift box (or something else completely), here are a few ideas to get you started:

Making your own bridesmaid proposal box

When putting together your own “Will you be my bridesmaid?” proposal idea, here are a few ideas to get you started:

  • Keep it simple with a cute card or hand-written letter to each bridesmaid.
  • Make the proposal gifts something that each girl (or guy if you are having bridesmen) can use on the wedding day (dress hanger, robe, pajamas, slippers, drinking glass, etc.).
  • If a cohesive look is important to you, make everything in the proposal box color-coordinated to your wedding colors.
  • Put together a gift bag of little things that each girl likes (make each bag unique to her). Get creative with the contents of the bag (her favorite candy, lipstick, books/magazines, food/snacks, drink, color, photo of the two of you, journal, pen, phone case, music/movie-themed, etc.).

Will you be my bridesmaid (empty boxes)

If you are putting together your own bridesmaid proposal boxes, you can start with these empty boxes that say “Will You Be My Bridesmaid” on them (one of the boxes is specifically for the maid of honor):

Crinkle cut paper to go inside proposal boxes

Here are a few options of crinkle-cut paper to add to your bridesmaid proposal box to make them look extra nice:

What to include in your bridesmaid proposal box (ideas)

When putting together your proposal box, the sky is the limit with what can go inside. Here are a few ideas for things you can include in your DIY proposal box:

  • A small (framed) photo of you and the bridesmaid who is getting the proposal gift box
  • Custom dress hanger for the bridesmaid dresses
  • Wine glasses
  • Tumbler
  • Shot glasses
  • Robes or pajamas
  • Coffee mugs (travel mugs)
  • Cookies (either Etsy or someone local to you)
  • Bridesmaid shirts for the bachelorette party
  • bath bombs
  • Robe or pajamas for getting ready the morning of the wedding
  • Slippers for the wedding morning
  • Journal and pen
  • Makeup bag
  • Clutch
  • Tote bag
  • Chocolate (Etsy or a local shop)
  • Candles
  • Tea
  • Soaps (maybe handmade soaps from local shops near you)
  • Cozy socks
  • lip balm
  • sweet treats
  • hair ties

Here are a few items to check out:

Bridesmaid robes

We love these satin lace bridesmaid robes from ModParty on Etsy.

3 bridesmaids wearing satin lace robes for the wedding morning
These satin lace bridesmaid robes are adorable!

Another shop to check out is LamarieeNewYork on Etsy.

A group of bridesmaids wearing robes with their hands in the air
Custom bridesmaid robes for all of your girls.

Sleepshirts (long pajama shirts) for bridesmaids, maid of honor, or matron of honor (plus the bride-to-be)

We love these monogrammed oversized sleep shirts (pajama shirts) from ModParty on Etsy.

3 bridesmaids wearing pajama shirts and slippers
Add a monogram for each bridesmaid or maid of honor

Check out these 50 bridal party pajama ideas for the bride and bridesmaids

Bridesmaid (Bride’s-Babe) beanie hats and cozy socks

ModParty on Etsy has an entire collection of “Bride’s-Babe” wearables. We love the beanies, t-shirts, cozy socks, and slippers. Visit their store to see all of them.

A bride and bridesmaids wearing cozy socks and beanie hats
These bride’s-babe cozy socks and beanies are adorable! Check out the Etsy shop to see all of the different items.

Custom hangers for bridesmaid dresses

We really love these simple personalized bridesmaid dress hangers from EverlyGrayce on Etsy.

Bridesmaids dress hangers that have the name Ashley on them
You can customize these dress hangers any way you like (bows, just names, bridesmaid, maid of honor, etc.)

We also love these wooden bridesmaid dress hangers from SeptemberAndGraceINC on Etsy.

wooden bridesmaid dress hangers on a table
We love the different colors of wood that you can choose from.

Bridesmaid socks

We love these cozy bridesmaid/bride/maid of honor crew socks from BlissfulSocks on Etsy.

bridesmaids wearing personalized socks on a bed.
These cozy socks are the perfect wedding morning accessory for the bride, bridesmaids, and maid of honor.

We also love these personalized bridesmaid socks by KOYSARsocks on Etsy.

The gray socks on the left are from one of our own weddings and we can confirm that these socks are so soft and look amazing!

bridesmaids wearing socks sitting on a couch
These socks can be personalized for the bride, bridesmaids, mother of the bride, mother of the groom, maid of honor, matron of honor, and more!

Slippers for the bridesmaids and maid of honor (and bride)

We love these white slippers from ModParty on Etsy.

Close up of bridesmaid feet wearing slippers
You can get these slippers personalized with names or the bride can wear slippers that say “bride” and the bridesmaids can wear slippers that say “babe”

We also love these comfy fuzzy slippers from TheToBeShop on Etsy.

close up of fuzzy slippers in multiple colors
These fuzzy slippers are amazing quality and can be customized however you like

Bridesmaid glasses

These personalized glasses from SweetClementinesCo on Etsy are beautiful!

bridesmaid champagne glasses on a table
These awesome champagne glasses come in rose gold, white, silver, and gold.

We also love these wine tumblers and skinny tumbler sets from WorkofHeartGifts on Etsy.

personalized bridesmaid glasses on a table
These bride and bridesmaid tumblers are so stylish!

Coffee mugs (travel mugs) from the bridesmaids and maid of honor

These personalized wedding Starbucks cups are such a fun and unique gift to give your bridal party. Made and sold by StarTangledArts on Etsy.

custom wedding starbucks coffee mugs
You can have these awesome Starbucks coffee/travel mugs personalized for the bride, bridesmaids, mother of the bride, maid of honor, mother of the groom, and the matron of honor.

We also love these stylish travel mugs by WeddingsByLeann on Etsy.

travel mugs with the words bridesmaid and bride on them
We love all of the color choices for these travel mugs

Will you Be My Bridesmaid Message Ideas

Here are a few fun captions to use in your bridesmaid proposal cards (or you can have these made into a meme if doing a virtual proposal via text):

  • It’s my turn to pop the big questions. Will you be my bridesmaid?
  • My “I Do” would not be the same without you!
  • If I told you there would be lots of single groomsmen, would you be my bridesmaid?
  • It wouldn’t be a bridal party without you. Will you please be my bridesmaid?
  • I promise not to make you wear an ugly dress.
  • Obviously, you’re going to be my bridesmaid, so let’s make it official!
  • I’ll only be a happy bride if my best friend is by my side.
  • Will you be my bridesmaid? All you have to do is show up (and hold my dress when I pee)
  • Please help me keep my sh*t together. Will you be my bridesmaid?
  • Will you be my dress-bustling, bouquet-catching, champagne-drinking, dance floor-slaying, bachelorette-partying bridesmaid?
  • So there’s gonna be this great party with an open bar? Wanna be my bridesmaid?
  • Pop the bubbly, I’m getting a hubby! Please be my bridesmaid 🙂
  • Will you join my bride tribe?
A bride and bridesmaids walking down the street together. This is for the best will you be my bridesmaid proposal ideas article.
How many bridesmaids are you going to be a part of your bridal party? This bride has 11 bridesmaids!

We have an entire post on funny and sweet bridesmaid captions and messages for Instagram (or whatever you need them for).

FAQ (Frequently Asked Questions) About Bridesmaid Proposals

There are so many questions you might have when choosing your bridal party. Here are some of the common questions that we hear (with our answers and opinions):

1. How soon should you ask your bridesmaids if they will stand by your side?

We recommend asking your friends and/or family to be your bridesmaids (or bridesmen) as soon as possible (8-12 months before the wedding is what you should shoot for). You want to give them enough time to take off work, plan any vacations they might be taking, plan your bachelorette party, plan your bridal shower, get their dresses, etc.

If you get engaged 18-24 months before you plan on getting married, you can hold off on picking your bridal party unless you simply don’t want to wait. Try to pick your future bridesmaids and ask them if they can do it 8-12 months before the big day.

2. Is it okay to text when asking someone to be your bridesmaid?

Yes, it is perfectly fine to do a bridesmaid proposal via text message. There are many times when a bride and her friends or family do not live near each other. Asking them to be a bridesmaid over the phone or text works great.

If doing a bridesmaid proposal through text message, we recommend using a funny caption, meme, or GIF (or it can be cute and sweet).

We also love this fun idea for asking someone to be your bridesmaid via text message (sending them a custom smartphone electronic card):

a phone app for texting someone about being your bridesmaid
You can customize the skin color, clothing, and hairstyle so that it closely resembles the bridesmaid that you are sending it to.

3. How do I ask my bridesmaids virtually?

If doing a bridesmaid proposal in person is not an option for you, you can simply do a virtual proposal.

Here are a few fun virtual proposal ideas:

One on one zoom or skype call

Tell each of your girls that you want to catch up with her over Zoom or Skype (because you simply need to see her face!). Then pop the question! Easy-peasy.

Send a bridesmaid proposal box

Do the same as above but send a bridesmaid proposal box in the mail and have her open it over Zoon or Skype so you can see her face.

Have a pizza delivered

To take it to the next level, have a pizza (or whatever her favorite food is) delivered to her house while you are on the zoom call. Also, have one at your house before the call starts (but don’t let her know it’s there).

*Make sure you order in advance so you can have it delivered at a specific time.

Then after you ask her to be your bridesmaid (while you are just chatting and catching up), her doorbell will ring. Then when she comes back to the call, you will be there with your pizza too. Now you get to enjoy dinner together!

This will make an amazing memory!

A group chat

This might be a little more difficult to set up, but it works the same as above.

You can simply get all of the girls (and guys if you have bridesmen) on a group Zoom chat and pop the question. Or you can send them all proposal gift boxes and tell them to only open the gift boxes on the group call.

*With any of these options, you should record the Zoom or Skype video call.

4. Do you send out save the dates before asking bridesmaids?

No, you do not need to wait for your save the dates to pick your wedding party. In fact, many couples don’t even send save the dates.

The average save the dates get sent out 6-8 months prior to the wedding date. You want to ask your wedding party about 8-12 months before the wedding date (if possible) in order to give them enough time to plan and get everything they need for the wedding day.

5. Who should be my bridesmaids?

Your bridesmaids (or bridesmen) should be those closest to you. Typically the bride-to-be chooses her sister/sisters, best friends, and maybe even her soon-to-be sister-in-law.

When choosing your bridal party, you want to make it easy on yourself. Don’t feel like you have to ask someone just because they are your sister or sister-in-law. If you are closer to a few friends than you are to your sister, then you should only have your friends included in the bridal party.

When choosing your bridesmaids, you want to think about the entire planning process. Chances are, your bridesmaids will also be going to your bachelorette party, bridal shower, rehearsal dinner, and spending your entire wedding day with you. That is a lot of time together. A time in your life when you want happy memories.

Some questions to ask yourself before asking anyone to be your bridesmaid:

  • Do I want to spend my entire wedding with this person?
  • Does this person attract drama wherever she goes?
  • Is this person always late?
  • Does this person complain a lot?
  • Will this person get along with the rest of my bridesmaids?

Once you honestly answer those questions, you will most likely know whether or not to have them as a bridesmaid.

6. How many bridesmaids should I have? How many bridesmaids is too many?

You should have as many bridesmaids as your little heart desires. If a giant bridal party is your jam, go for it. But if you normally do better in smaller groups, you should probably just have a few.

If you feel like a getting-ready room with 12 girls having hair and make-up done will stress you out, a big bridal party is probably not for you.

The average number of bridesmaids in a wedding is 5-6. We know this because we have planned and photographed about 500 weddings over the past ten years, and a high percentage of those weddings (I would say 75%) had 5 or 6 bridesmaids.

The smallest amount was zero (0). We have seen quite a few with only 1 or 2 on each side.

The largest bridal party we ever worked with had 13 bridesmaids, 12 groomsmen, and six flower girls/ring bearers. Ten of the bridesmaids for that wedding were sisters of the bride!

Another thing to consider when deciding on how many bridesmaids to have is time. Everything is going to take longer with a larger bridal party.

  • Hair and make-up will take a lot longer
  • Traveling to and from hotels, venues, photo locations, etc.
  • The ceremony processional and recessional
  • Receiving lines (if you are doing one)
  • Posed photos
  • Reception intros

Just budget extra time for all of those things if you have a bigger bridal party.

Our advice to you is to have as many as you are comfortable with.

7. Do you have to ask someone to be a bridesmaid if they asked you?

No, you do not have to feel obligated to ask someone to be a bridesmaid if you were one of their bridesmaids.

Every wedding is different. You do not need to feel pressured into adding more people to your bridal party just to make room for every previous bride that you stood up with.

Make your bridal party the exact group of friends and family that you want. This is your wedding day.

8. How do I ask my future sister-in-law to be my bridesmaid?

You can simply ask your sister-in-law to be your bridesmaid the same way that you are asking the other girls. If you want her to be a part of the bridal party, just include her in everything the same way you would if it was your real sister or one of your close friends.

You can give her a card that says something cute like: “Soon you will be my sister, but until then, will you be my bridesmaid?”

9. What should be in a maid of honor proposal? Should it be different than the bridesmaid proposal?

If you want to do something extra special for your maid of honor, you definitely should. Don’t feel bad about doing more for your maid of honor than the rest of your bridal party.

If you feel awkward about it, just do it on the side and not in front of the other girls.

For example, maybe you are only giving the bridesmaids a cute card asking them to be your bridesmaid.

You could give your maid of honor a special card but also include a piece of jewelry, a bottle of wine, or something really nice like a day at the spa together.

If you are having two Maids of Honor or a Maid of Honor and Matron of Honor, you could get them each something extra special.

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