Say Yes To 59 Awesome Bridesmaid Proposal Ideas | Sandals (2024)

Planning a wedding can get pretty crazy. One minute you’ve got over 12 months to play with, and the next you’re practically walking down the aisle! Before getting to that point though, there are lots of things to think about, like decor, invites, venue, location, and so much more.

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Other than planning the logistics of the ceremony, if you’re the bride, you’ll also need to figure out who your bridesmaids will be and how you plan on asking them. Many brides don’t give much thought to popping the “Will you be my bridesmaid?” question – but it’s a question that requires finesse, and some level of charm. If you’re unsure of how to proceed, here are some practical bridesmaid proposal ideas we’ve compiled that are sure to help get your besties to come along for the most exciting ride of your life!

Insider tip: Still thinking about where to tie the knot? Consider a Sandals all-inclusive wedding which will take the planning out of your hands and put it into the hands of the experts!


Special hand-written or printed card proposals

Cards are a simple yet wonderful way of letting someone know how much they mean to you. They’re also great for proposals of just about any kind, including bridesmaid proposals. Here are a few ideas for cards that can help you to ask your friends the question of the day:

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1. Hand-made or custom card

A custom-made item is a nice way to add a personal touch to any gift or card. A handmade card is even better because then you get to select any style or design of your choice. This shows that you’ve invested some time into creating something you know will be appreciated.

2. Silly bridesmaid proposal card

A bridesmaid proposal card doesn’t always have to be formal and business-like. Lighten the mood by adding a silly line or two or even an “inside joke” only you and your bridesmaids-to-be would know about.

3. Let’s do this card

If you feel like cutting to the chase, a “Let’s do this” card gets straight to the point and lets your bridesmaids-to-be know that you mean business.

4. Creative bridesmaid invitation

A little creativity never hurt anyone. These might even be the cherry on top when it comes to your bridesmaid invite! Lure in those special women who’ll help ensure everything about your wedding day goes smoothly. Unique designs are cool, and you can also include a famous line or two from your favourite singer or actor.

5. Scratch-off card

This type of card builds up the excitement and fun by letting your bridesmaids put in a little work to finally uncover the big secret. Each lady will have to scratch her card to find out exactly what’s hidden underneath, and only then will the exciting news be revealed!

Bridesmaid proposal gift boxes

Who doesn’t like getting gifts? Giving one to your potential bridesmaids may be just what you need to coax them into saying yes. There are different bells and whistles you can include with these gift boxes. Here are some ideas:

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6. Goodie boxes

Gift boxes are another way to present your proposal to your closest friends. The best goodie boxes have room enough to include lots of treats, trinkets, and even jewellery while making a proposal of a lifetime.

7. Custom gift box

A customised gift box is a cute bridesmaid proposal idea. There are tons of designs you can reference to create your own or get one customised by a company. You can print the bridesmaid names on the outside and fill the inside with treats and snacks they’ll love.

8. Pop-up box

The pop-up box is a whole lot more exciting than a simple bridesmaid box. This type of box will leave your bridesmaid in awe when she opens it up and out pops a beautiful display in colour. As a bonus, you can fill it with whichever treats you think your bridesmaids will enjoy.

9. Gift with a secret message

If you want to add some mystery to your bridesmaid proposal, why not give your potential bridesmaid a present and slip your proposal in the package? You can gift her with a few bottles of wine or even a blouse you know she’s always wanted. You can slip an envelope inside with your request.

10. Proposal bomb box

Proposal bomb boxes are a fun way of popping the question. As soon as the recipient unwraps and opens the box, it pops open to reveal your secret. You can also personalise these bomb boxes to include the names of your beloved bridesmaids-to-be.

11. Engraved bridesmaid proposal box

Bridesmaid proposal boxes are simple and memorable, and an engraving at the top of each box will be a sweet gesture. These make great mementos and can even be used to store jewellery and other personal effects.

12. Treat them to some spa products (spa day box)

A gift of spa products inclusive of mineral masks, essential oils, shampoos, candles, and bath products is a sweet way to let your bridesmaids know you care about them. You can include your invite inside the box!

Insider tip: Got the wedding planning jitters? Go for a Caribbean resort like Sandals for an experience that comes with a dedicated Sandals Wedding Planner who’ll help you get everything you need in order ahead of your big day!


Propose to your bridesmaids with the best feel-good treats

Your pre-wedding shenanigans won’t be complete without a spa treatment to help you and your bridesmaids relax before the ceremony. Options include finding a great spa you can all go to or bringing the spa to your bridesmaids-to-be in an unexpected way. Here are some great options we like:

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13. Spa treatment

Spa days are great for connecting and relaxing. Find out when everyone is free and set up a day when you can all have a chill time together indulging in exotic spa treatments. After everyone is all pampered, you can make your special announcement and extend the invitation!

14. Spa-style face masks

If you don’t feel like heading to the spa, why not transform your home into one? To make this possible, you’ll need to head to the beauty store for some supplies. You can pick up lotions, essential oils, body scrubs, face masks, and other indulgent treats. You can also go the DIY route for face masks, which is something you can all do together. The next step, of course, will be popping the big question!

Insider tip: Speaking of spas, you and your wedding party will be in the lap of luxury and indulgence at the award-winning Sandals Red Lane® Spa. You’ll be able to find the rejuvenation and relaxation you and your bridesmaids need and so much more!


Things they can wear make a great bridesmaid proposal gift

Put some smiles on the faces of your future bridesmaids by gifting them with clothing items they might even be able to wear to your hen do! You can shop around for some comfy PJs – anything cute and cosy will do. Remember, a personalised touch is always well-received!

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15. Bridesmaid t-shirts

Gifting your bridesmaid with customised t-shirts is a neat way of helping them to support you during this important milestone in your life. You can include catchy slogans like ‘bridal duty’, ‘the bride tribe’ – basically anything that adds to the fun and excitement of your big day!

16. Silky satin robe

A smooth, silky satin robe can be a great gift for your bridesmaids-to-be. These are so soft and comfy that they will surely help your bridesmaids mellow out as they get their hair and makeup done for the wedding. You can gift one of these to each of your bridesmaids, along with a handwritten invitation!

17. Bridesmaid hair ties

All your bridesmaids should step out in style on your wedding day with their hair adorned with the latest and fanciest hair ties on the market. Remember, these ladies represent you so be sure to help them to represent you well!

18. Bridesmaid jacket

If you feel like switching up the traditional dress code, a bridesmaid jacket adds an edge to the regular bridesmaid dress. It’s both trendy and cute and the custom-made ones can feature any interesting quotes you come across.

19. Luxe sleep mask

Planning a wedding can be hectic and chances are your bridesmaid is going to want to get some shut eye whenever they can. Help them out a little by gifting them with a luxe sleep mask to help them relax and get some much-needed rest.

20. Temporary tattoos

Live on the edge (but not really) with some cool temporary tattoos you and your bridesmaids can rock at your hen weekend, or even at your wedding. You can all get in touch with your creative and somewhat rebellious selves with some rad temporary tattoos. This will definitely be the gift that keeps on giving, and a memory you won’t soon forget!

21. Personalised sunglasses (and box)

Imagine your girls stepping out in their very own pair of personalised sunglasses in honour of your wedding. Sounds pretty cool right? Box these up along with your invite. They will certainly make a statement at your hen do, so get yourself a pair as well!

22. Personalised pyjamas

Buying personalised pyjamas for your nearest and dearest is a sweet gift option that’ll show you care about the comfort of your bridesmaids-to-be! Make this gift complete by adding some sleep masks to the package.

Insider tip: Want to have a wedding and holiday in one? You can get a free Sandals wedding with a minimum 3-night stay inclusive of an amazing venue, a bouquet, a boutonniere, and even a gorgeous cake you’ll be able to cut against the backdrop of paradise!


Things they can eat will get you a quick ‘Yes!’

Your bridesmaids will surely get hungry along the way and, in between meals, they might want to have a few snacks to keep them going. Here are our top picks for sweet treats they’re sure to love:

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23. Cupcake mason jars

People find lots of fun ways to enjoy their favourite foods and cupcakes are no different. Rather than simply serving them in cupcake liners, you can put them in mason jars - this way they’ll be able to keep the jars (which hopefully are wedding customised!) when they’re done.

24. Biscuits with printed or icing messages on top

Can anyone really say no to some delicious cookies? Especially with icing on top with cute messages, these will be a delicious treat for your ladies to savour. The best part is that these can be made in different shapes, sizes, colours, and flavours. Go for red, heart-shaped biscuits for a touch of romance!

25. Custom M&M’s (sweets)

This treat can be made extra special in honour of your wedding day. Start by customising them with the faces of your friends or even phrases like “Best Friends” or “Friends Forever.”

26. Box of chocolate

Chocolate is a dessert item you can play around with, and it also makes a great gift for your bridesmaids. Take your pick of the many brands your troupe will love and include your proposal inside the box of chocolates!

27. Lollipops with a twist

Yummy treats on a stick – this is one gift just about anyone would be happy about receiving. Take your pick of the many vibrant colours, find a size that suits you, or even go for gourmet selections with a nicely sealed bridesmaid proposal envelope on the side!

Insider tip: A little inspiration never hurt anyone! Take a look at these amazing wedding inspiration ideas you might be able to incorporate into your big day.


Propose to your bridesmaids with things they can drink or drink from

28. Custom tumbler

Your bridesmaids should be able to enjoy a drink or two in style, and a fancy tumbler is just the way to do it. These come in a range of colours and can be customised to include any design of your choice. For the sake of holding onto memories, your bridesmaids will be able to keep these long after your wedding!

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29. Custom wine with a customised label

Let the wedding fun begin with a bottle of custom wine! Take things to another level by placing a label you and your future bridesmaids will love… perhaps the wine label can contain your proposal or something sweet you love about each lady? Find out whether they love red or white wine, and you’ll be good to start planning! Add a handwritten note for a personal touch.

30. Personalised shot glasses

A wedding is a celebration of love with friends, food, and, more than likely, alcohol. Make yours truly memorable by personalising some shot glasses before gifting them to your bridesmaids just ahead of them setting off on the journey with you to an amazing wedding day!

31. Personalised stemless flute

Fizzy drinks will definitely look (and perhaps even taste) better in a flute that has been customised for each of your bridesmaids. From your hen to your wedding, they’ll be able to enjoy their favourite sparkling drinks in this personalised gift.

32. Customised bridesmaid mug

A hot cup of tea or coffee is best enjoyed from an insulated mug that keeps the drink warm. Breakfast on the go, or rather, tea on the go, does not have to be a dull affair. Mugs can be customised to include inspiring or romantic messages on the side, and this is something your bridesmaids will for sure appreciate.

33. Custom drink sleeve

Drink sleeves are a convenient way to carry your favourite drink with you when you’re on the go. A customised version for your bridesmaids is a good way to inspire them to stay hydrated while planning the wedding with you.

34. Custom wine glasses

A customised wine glass will go great with a bottle of wine and the customised label we described earlier. This wine glass can include the bridesmaid’s name and even your wedding date – that way she’ll always remember the moment she shared with you.

35. Water bottle

A gift of a water bottle can help ensure your friends have a way of storing the most essential drink when they’re out and about. It’s easy to customise as well and is one of the most sensible presents you can give.

36. Mini champagne with custom labels

Champagne is one of the best drinks to have for any celebration. A bottle of mini champagne with a custom label designed by yours truly? Even better! Your bridesmaid might even choose to slip this into her bag to save a bit of fun for later!

Insider tip: At Sandals, five-star premium liquors are included in your all-inclusive package. There are as many as 11 bars per resort, including swim-up bars and over-the-water bars with expert bartenders waiting to serve signature co*cktails, and so much more!


Jewellery or something to keep it in works well for bridesmaid proposals

37. Personalised locket

A locket is a small but sentimental gift that allows you to wear your favourite memories around your neck. Have a little fun with a gift like this one by including pictures inside of you and your friends, or simply take the opportunity to pop the question.

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38. Earrings in a cute proposal box

Most women love the idea of receiving a pair of earrings as a gift. In this case, earrings can serve two different purposes: As a simple gift with your proposal inside the box, or as a jewellery item to match the bridesmaid dress. Either way, it’s a win.

39. Bridesmaid invitation bracelets

Bracelets are another item of jewellery you can give someone and be pretty confident they will like it. Again, the bracelet can match the wedding dress, and the box can be customised to include your proposal inside.

40. Handmade ring dish

Ring dishes are beautiful and elegant, and you can choose from unique, custom, or even handmade options. These can be used to store various jewellery items. Your bridesmaids will love the thoughtfulness of this proposal gift!

Propose to your bridesmaids with fun things for around the home

41. Bridesmaid bath bomb

Bath bombs for bridesmaids are all the rage. These often come pre-wrapped in a clear bag (glittery or not - your choice), and you can have your pick of the colour ribbon included with each individual gift. Pair this with a handwritten proposal card, and you’re likely to get many yeses!

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Photo credit: Kostikova Natalia/Shutterstock.com

42. Bridesmaid candle

Candles are often included in weddings. Even before the ceremony, you can set the tone by using some one-of-a-kind candles in your bridesmaid proposal. Try adding some fun phrases on the candle jar, or even asking the big question in bold print!

43. Mini succulent

Plants speak life and getting your bridesmaids small and easy-to-maintain plants like a succulent is a thoughtful way to go. You can choose between the real deal and artificial versions that are just as adorable as she is!

44. Bridesmaid hanger to go with their dress

What better way to add a little pizzazz to the closet of a bridesmaid-to-be than with a personalised bridesmaid hanger? This can be part of your proposal, and each hanger can include their name and title, for example: “Caroline: Bridesmaid.”

45. Bridesmaid tote bag

Tote bags are a must for every woman. When planning your wedding, you might want to give one of these as a gift to your bridesmaids-to-be. Custom totes (and your exciting news!) will definitely be something your bridesmaids will smile about.

46. Personalised bottle opener

A personalised version of a bottle opener can include your proposal on the handle or your bridesmaid’s name. Instead of simply gifting it by itself, you can add it to a gift box that includes wine or champagne.

47. Bridesmaid Christmas ornament

Two special occasions can be integrated with one special gift: a bridesmaid Christmas ornament. If your bridesmaid is a big fan of Christmas celebrations, then a gift like this would make her very happy and she will be glad to have a reminder of your special day too.

48. A floral delivery

A beautiful bouquet of flowers is a sweet and heartwarming gesture for your bridesmaids. Better yet, add a little note with your proposal so they know just what it is all about.

49. Framed photo

One can never have too many picture frames. Bring some pictures of you and your best gals from social media to life as you pop the question. You can encase each photo in a picture frame with your proposal etched along the borders. Your bridesmaids will be delighted with the memories this gift brings.

50. Bridesmaid proposal pillow

Pillows that have been customised to include your request are sure to be appreciated by the lovely ladies who’ll stand by your side on your wedding day. Long after the nuptials, this proposal pillow will serve as a fond memory that can also help with getting a good night’s rest.

51. Bridesmaid keychain

Similar to the personalised bottle opener, a bridesmaid keychain is a small but handy gift item. They can both be added to a bunch of keys and the bridesmaid keychain will serve as a reminder of her role in the nuptials.

52. Personalised luggage tags

If your wedding is taking place across the state or out of the country entirely, then a personalised luggage tag will be a cool gift for your bridesmaid-to-be. Personalising it to include “Bridesmaid” on the tag, is a way of instantly letting them know what the present is all about.

Insider tip: There’s hardly anything that can beat a destination wedding… except perhaps a destination wedding and honeymoon combo, which is entirely possible with Sandals Honeymoons! With a Sandals honeymoon, you’ll be able to enjoy gourmet dining at up to 16 specialty restaurants per resort, land and water sports galore, day and night entertainment, and luxurious suites created with romance in mind!


Other fun options to propose to your bridesmaids

53. Make bridesmaid recipes

A bridesmaid ‘recipe’ highlights what you love most about each bridesmaid and the friendship you share with them. This is something you can create yourself, and it is a great way of honouring the ladies who’ll serve as your bridesmaids.

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Photo credit: Gladius Stock/Shutterstock.com

54. Get matching mani/pedis in your wedding colours

A wedding is a perfect reason to be pampered. Get into a mode of comfort and style by heading out to get some matching manicures and pedicures with your bridesmaids before you pop the question. If you’d like, you can get them matching bottles of nail polish with the big question printed on the label.

55. A balloon proposal

Balloons are the ultimate celebratory item, so take advantage of this and literally pop the question with a couple of balloons. This will surely add to the excitement of the upcoming wedding.

56. Champagne mini piñata

Piñatas always add some excitement and fun, and you can make a champagne mini piñata to let your bridesmaids-to-be know how you would like them to be a part of your wedding. The piñata can be stuffed with all sorts of treats, and you can add your proposal to the mix.

57. Confetti poppers

Confetti poppers are those party items that are practically begging you to have a good time. Make good use of them and ask your bridesmaids-to-be all the questions you want and be prepared to answer a few from them too.

58. Unravelling ribbon

If you’re a lover of suspense, you’re going to love the eager looks on the faces of your future bridesmaids when they begin to unravel the mystery ribbon – this is the only way they’ll be able to read the secret message it holds. This process will be rewarding for all, and you will be ecstatic when they finally say yes!

59. Pop-me proposal balloon

Another element of suspense and surprise can be found in these unique pop-me proposal balloons. This will be an entertaining way of pitching your proposal and seeing the ladies all excited to share the moment with you!

Bridesmaid proposal ideas that will get you yeses all around!

Now that you have this comprehensive list to work with, we’re almost certain you have what it takes to win over the lucky ladies who’ll play a crucial role in getting you down the aisle. Match these ideas up with your budget and the personalities of the friends or family members you’ll be asking. Then, you’ll be all set.

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If you’re still not sure about a location, Sandals resorts in Jamaica, Sandals in The Bahamas, Sandals in Saint Lucia, Sandals in Antigua, Sandals in Grenada, and Sandals in Barbados are all amazing all-inclusive resort options for couples!

Insider tip: Amazing weddings and Sandals are almost synonymous. Take a look at these real Sandals weddings that came to life on the property – and ended with a happily ever after!

Say Yes To 59 Awesome Bridesmaid Proposal Ideas | Sandals (2024)
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