17 Amazing Bridesmaid Proposal Ideas: A Guaranteed Yes

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by  Kate Parker | Last Updated: 
bridesmaid proposal ideas

You’ve had the fairy-tale engagement, the wedding date is set, and now it’s finally time to decide on your bridal party. 

Bridesmaids are a tradition as old as time and asking your closest friends to be yours will be a significant moment you’ll both never forget. 

Stuck for ideas to show just how to go about it? Here are 17 fun ways to pop the question. 

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17 Amazing Bridesmaid Proposal Ideas That are Impossible to Say “No” To

Because you will likely be asking a fair bit from your bridesmaids in the coming months, why not think about how you could make your bridesmaid proposals extra special – they are your best friends, after all.

Whether you go crafty or luxe, budget or DIY, there is a perfect bridesmaid proposal out there for you. The important thing here is to show your friends how much you mean to them…and make it impossible for them to refuse!

An Oldie but a Goodie – the Bridesmaid Box

Let’s start with the bridesmaid proposal idea you’ve probably already seen all over social media. And for good reason too, a bridesmaid box is extremely Instagram-able and can cater to any budget. 

A bridesmaid box is simply a box that you can personalize and fill with goodies that can be used on the day of your wedding, and also keepsake items to remind you both of your friendship. 

I love this particular idea because it can be completely customizable to your budget.

If you fancy splurging, there are plenty of online businesses that can create personalized packages, right down to the proposal stenciled on the outside and cute monogrammed silk robes on the inside. 

I love Kate Aspen’s pink and gold gift boxes for a classic girly look, complete with trinkets, magnets, sunglasses, and more. 

For a slightly more budget-friendly option, Etsy has lots of options for doing it yourself, right down to the flatpack boxes with personalized stickers to add on yourself. I love these little flax boxes for a creative touch, hey, sometimes the smaller the gift, the more sentimental.

Why not have fun with it and pick a theme for your bridesmaid boxes, depending on the duties your bridesmaids will be doing and the season you’re in. Here are some easy ideas to get you started.

  • Spa and wellness
  • Makeup
  • Pajamas and slipper set
  • Champagne and chocolate 

Sweet Treats to Sweeten the Deal

There are so many fun options to choose from here. Say ‘will you be my bridesmaid’ via their stomach. 

Do your future bridesmaids have a killer sweet tooth and a ‘dad joke’ sense of humor? These delicious glazed donuts come with ‘I donut what I’d do without you’ written into the icing. Cheesy, yes. Irresistible, also yes.

If puns aren’t your thing (and if that donut pun had you cringing) then how about something a little more sophisticated? These trays of macarons with stenciled piping have my tick of approval, and how about these butter cookies with personalized fondant icing? 

Unless you are a whizz with a food processor and a piping bag, I recommend leaving this one to the professionals and enlisting the help of a cake shop to make your sugary dreams a reality. 

Or, if you aren’t one for big gestures at all, consider a good old tub of Gold Belly’s ice cream tub packs for your proposal. They come with the question on the top of the tub and will guarantee to send your besties into a happy sugary coma shortly after opening. 

Something Small They’ll Treasure for Life

If you want to give something that will last beyond your wedding day, why not look into having personalized keyrings made up for each bridesmaid?

It’s something practical but also sentimental and will show your friends just how much thought went into their proposals.  

I love this macrame keyring with the question popped on the card for a sweet, boho look. 

Other materials like leather, platinum, and wood would make for lovely keepsake keyrings as well. 

A Candle for the Relaxing Vibes

Nothing says comfort and self-care like a candle. Get off on the right foot with your bridesmaids by making them feel relaxed and calm, because who knows how crazy things will get in the lead-up to the wedding.

Go a little bit extra by designing the label yourself and it’ll remind them of your friendship every time they light their candle. 

Pick a look and smell depending on what you both have in common, like a favorite scent you both share, or a style of the jar that fits in with your home aesthetics.

I love the look of these glass jars which are customizable via a sticker you can write yourself. 

Wine to Get Them in the Party Mood

Ask her with a bottle of wine or champagne in hand and it’ll surely be appreciated. Drink it together to celebrate or save it for the bachelorette party, either way, you’ll be sure to earn brownie points here.

This custom-label website gives you lots of designs to choose from and even lets you design your own from scratch to make for a unique and personal gift.

This idea makes for a great thank-you gift as well, so if you accidentally already blurted out the question, make it right by saying thank you with your personalized bottle of wine. 

Let the label do the talking for you and I’m sure the answer will be a resounding ‘yes’.

And for a slightly different take, these wine bottle sleeves also make for a funny, quirky proposal. 

A Tee for All Occasions

I love this idea for its simplicity. An oversized tee will get pulled out time and time again, long after it’s been used as the getting-ready top on the morning of your wedding. 

Make your bridesmaids feel like a proper girl gang with their matching tee, and you can all enjoy your very own Pink Ladies moment together.

This retro maid of honor shirt ticks all the boxes for being effortlessly cute, comfy, and fun. 

A Tote Bag for the Environmental Queens 

Why not say no to plastic and unnecessary packaging and invest in a set of reusable canvas tote bags. They guaranteed to last the test of time and are personalized to make each bridesmaid feel special.

I’m a big fan of these ones here because the message can be tucked away on the inside, giving your friends their own little surprise when they see your hidden question. 

Plus your bridesmaid will never get caught out at the supermarket or farmers market again without a reusable bag on hand.

Jewelry for a Delicate Touch

If you do want to gift a present they will treasure forever, why not matching necklaces or earrings?

This will likely come at a higher cost than other ideas but if those matching friendship bracelets you made in middle school could do with a revamp, then why not look at a piece of jewelry for your bridesmaid proposal? 

These little initial necklaces by Monday Monarch scream bridesmaid gift. If you want to spoil your friends with something they won’t want to take off, I say splurge on these beauties.  

For a cheaper but equally cute alternative, these little charm bracelets would make for a beautiful proposal gift.

Overnight Bags with Monogram Detailing

Planning to whisk your girls away for a night, or just want a matching bag for everyone to use on your wedding day to get ready with?

Monogrammed overnight bags are a stylish way to get your bridesmaids feeling excited about the wedding. 

These cotton canvas ones by SSWeddings have leather accents and a leather embossed personalized label and fit perfectly in the overhead bin. Bachelorette party in Las Vegas? Luggage for the crew is sorted.

Also, consider the type of wedding you’re having when deciding which bag would be most suitable. I once went to a destination wedding for my friend, and she gave us all beach bags with our initials on. They were such a hit!

If you’re near a beach, then why not go for these adorable retro jelly baskets for their throw-back feel. It’ll be like you’ve been transported back to summer times as a kid. You’ll just need the jelly shoes to match next.

Personalised Tumblers for a Chic Gift

Tumblers can get a bit of flak for being a bit basic, but don’t let that stop you from using them in your bridesmaid proposal. 

Rather than the ever so popular rose gold or marble designs, I recommend neutral shades and pastel colors, made from long-lasting ceramic, stainless steel or glass.

Whether you want to keep your girls hydrated or just keep their wine cool while you party in the sun, a personalized tumbler could be a great addition to your bridesmaid gift box, or as a standalone gift. 

Perfect to bring along to a night out together, I love these wine tumblers by the Bridesmaids Gifts Boutique. Each one of your bridesmaids is turned into a cartoon to appear on the front of the tumbler. There’ll be fits of laughter as your friends each discover themselves in caricature form.  

A Plant to Brighten Their Day

Not every bridesmaid proposal needs to be extravagant. How about a simple houseplant with the message ‘I Plant Get Married Without You’? 

It’s unique, your friends will probably be appreciative of some more greenery (who doesn’t love a house plant?) and it’s a sweet gesture of friendship. 

RallyandRoots sell beautiful handmade terracotta pots with your message painted on with acrylic paint. 

Message in a Bottle for a Timeless Throwback

How about taking notes from ancient philosophy with a message in a bottle

Your friends will be telling everyone for weeks about how cute your proposal was, and how they felt the moment they unwrapped the scroll to see the words ‘will you be my bridesmaid’. 

If you send a message in a bottle as your bridesmaid proposal, your friends will treasure it for years to come. 

Makeup Bag with a Secret Message 

Do you have friends who are always following the latest beauty trends? Maybe they would appreciate a makeup bag gift with the question tucked away beneath the zip?

I love Pink Positive’s brushed cotton canvas cosmetic bags for the large amount of personalization options and the beautiful scroll handwriting font used.

A Heartfelt Card to Tell Them How You Feel

More of a minimalist? Then how about just saying exactly how you feel in a card, with a photo of the two of you together? 

Sometimes the best proposal is the one from the heart and this simple card design from Star Seller will be sure to tug on the heartstrings, as your friends can reminisce on your amazing friendship through the ‘Will You Be My Bridesmaid’ photocard.

Pop A Balloon and the Question

For every minimalist, there’s that friend that loves the limelight and being the center of attention. If this sounds like your soon-to-be-bridesmaids, give them their moment by taking them all out to a girls lunch and presenting them each with a balloon. Have them pop the balloon to get to the scroll tucked inside so they can read your question. 

You’ll be popping the question in the most literal sense and get to watch your friend’s reaction as they follow the instructions. 

For a little bit of DIY, this package from A Little Something lets you create the box, card, and balloon message, right down to the pop me a sticker with a wooden pop stick. Surprise your bridesmaids with a proposal they’ll never forget. 

Handmade Keepsake Heart

There’s just something nice about supporting a small business, and that’s what makes this gift feel like a lovely touch. 

Holly Emily Designs have created these handmade keepsake hearts for brides to gift to their bridal party. Made from clay and paint, you can choose to have any message you like painted on, making them a totally unique way to surprise your friends. 

Each heart also comes with a jute hanging, so your bridesmaids will be able to hang their hearts where they can see them every day. 

 The Surprise at The End of the Drink

This is quite possibly the sweetest way to propose to your bridesmaids but will work only if you can ask the question in person. 

These plain white ceramic mugs from the Letter Loft don’t look like much at first glance, but after you pop the kettle on and make you and your soon-to-be bridesmaid a cup of tea, you get to sit back, relax, and wait. 

When your (hopefully unexpecting) friend finishes their drink, they’ll see the words ‘Will you Be My Bridesmaid’ on the bottom of the mug. Film their reaction and you’ll be laughing about it all the way to the bachelorette party.

These mugs are sure to create a special moment shared between you and your best friend and would make for the perfect way to ask the question to your maid of honor.


Figuring out how to propose to your bridesmaids can be a really exciting step in your wedding plans, and when you have them all by your side, you’ll feel capable of even the most stressful of wedding jobs.

Hopefully, you enjoyed these 17 bridesmaid proposal ideas and you’re now feeling full of inspiration to go out and ask the question. Good luck!

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