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48 Ways to Propose to Bridesmaids (and Groomsmen)

Posted by Lovepop Team on

Bride and Bridesmaids celebrating wedding at the beach

If you've ever been in a wedding party, you know it's a huge honor and a significant commitment. The role is an investment of time, money, and energy. From bridesmaid dresses to bachelor parties to emotional support on the big day, your wedding party will be doing a lot for you. 

Of course, most of these special people will be happy to help you; after all, it's an honor to stand beside a friend or family member on their wedding day. So, what are the best ways to ask your bridesmaids and groomsmen to join the inner circle, AKA your wedding party?

Make your wedding party proposals personal and valuable. Obviously, you won't give a gift as fancy as the engagement ring, but ideally, it will be a meaningful & practical gift. 

Bridesmaid Proposal Ideas

If you're looking for bridesmaid proposal ideas or ways to ask groomsmen to participate in your wedding, here are some sweet ideas to consider. 

  1. Custom makeup or toiletry bags 

Custom toiletry or makeup bags can be useful on the Big Day and helpful for travel. Plus, there are lots of adorable styles to choose from! For example, Etsy boasts various sweet monogrammed pouches made by independent artists, or you can search for sustainably made makeup bags & have them monogrammed by a local embroidery shop. 

  1. Make sure their luggage doesn't get lost 

Many people travel regularly, but most do not label their luggage correctly. Custom luggage tags are a perfect invitation to your bridesmaids or groomsmen to come along for the ride. Help them keep tabs on their bags as they travel to the wedding. Many shops sell engraved luggage tags, or you can personalize them.

  1. A customized cooler can

Koozies are good wedding favors, but ordering custom Yeti cups for the members of your wedding party is a terrific way to invite them to join in the fun (and imbibe while they're at it!) Choose cups & vinyl in your wedding colors or your bridesmaid's favorite colors. Then, write a note asking them to join you as you eat, DRINK, and get married! 

  1. A bottle of champagne

Simple but classic. How do you ask bridesmaids to celebrate with you through the entire journey of your wedding? Send a delivery of a fancy bottle of bubbly with an adorable Lovepop Champagne Celebration card. They'll be bubbling with excitement when you ask in this thoughtful & fun way. Get it? Bubbling? 

  1. Host a dinner for all the girls 

Another oldie but definitely a goodie. Maybe you're still trying to find the perfect way to share your bridesmaid proposal message. Invite your girlfriends to dinner or a night out for cocktails and "propose" to them all at once. Then, of course, pick up the tab! 

  1. A portable charger

Weddings suck the life out of people, and they also suck the life out of iPhone batteries. So, save the day by ordering cute portable chargers for your wedding crew when you ask if they'll join your big day. Create a small basket with a couple of spa items AND the charger with a note about recharging during wedding season! 

  1. A rose bouquet & a rosé

Play a riff on The Bachelorette's "Will you accept this rose?" You may want to deliver a Lovepop Rose Bouquet to each wedding party member. Better yet, pair it with a little bottle of pink drink that reads, "Will you accept this rosé, too?" They will enjoy the creative ask & undoubtedly feel the love! 

  1. A handmade customized gift box 

If you are crafty & enjoy curating unique gift packages, seek out some inspiration and create your own gift! Include customized items based on each bridesmaid's interests. Some ideas include a custom candle, a "You've Been Chosen" Toy Story pop-up card, an engraved necklace or bangle bracelet, and a bridal party t-shirt or "tie the knot" hair ties. 

  1. A budget-friendly gift under $15

Giving gifts to several of your closest friends can add up quickly. If you want to propose to your bridesmaids but keep it budget-friendly, try one of these cute ideas: 

  • A sprinkle donut in a box with a note saying, "I donut want to get married without you!"
  • A ModParty bridesmaid proposal candle
  • A bridesmaid balloon pop proposal box 
  • A personalized tumbler, keychain, or tote bag
  • A pop-up white flower basket with a meaningful note inside
  1. Bridal party apparel

Bridal parties love having adorable matching clothing just as much as they enjoy custom accessories. From jean jackets to slippers, there are so many apparel items that you can order & customize for your bridesmaids. If you want to give them a gift they can wear, try a sweet proposal card with a bridal party t-shirt, pajamas, or robe.

Bridesmaid Proposal Messages

Wondering what to write in a bridesmaid proposal card? We've got you covered with fabulous ideas for asking your bridesmaids to stand beside you. And we have the perfect cards to write them in, including a fizzy, fun champagne pop-up card and a romantic & whimsical hot air balloon card.

  1. Sisters share childhood wishes & grown-up dreams. I hope you'll stand beside me at my fairy tale wedding!
  2. I want to become a bride with you by my side! Will you be my bridesmaid? 
  3. You've always been like a sister to me. Will you stand beside me on my wedding day? 
  4. My turn to pop the question! Will you be my bridesmaid? Please say I do! 
  5. You've always said you'd be there for me if I fall. Will you hold the train of my dress so I won't?
  6. I can't wait to be sisters... but until then, will you be my bridesmaid?
  7. Will you be my bridesmaid if I promise there will be single groomsmen? *Wink*
  8. I can't make all of these decisions without you. The only detail I know is that I want you to be my Maid of Honor! 
  9. All you need is love and champagne! Will you celebrate by my side on my special day? 
  10. You think this party is fun, but wait until the main event! Will you be my bridesmaid? 
  11. You've been by my side through laughter and tears for so many years. Will you pretty please be my bridesmaid? 
  12. When I imagine wearing a wedding dress, I always imagine you beside me. Will you make my dream come true? 
  13. Something old, something blue, something borrowed, just need YOU! 
  14. You've been with me through thick and thin. Won't you please be there when I marry him? 
Champagne Bottle Pop-Up Greeting Card

Groomsmen Proposal Ideas

Proposing to your groomsmen is a trendy way to let them know you want them to join your wedding party. There are lots of fun gifts & unique ways to ask your favorite guys to stand by your side on your wedding day. 

  1. Take them golfing

Make some fun memories with the guys when you make the ask. You can bring personalized golf balls with their names on them. Once everyone arrives at the driving range or golf course, present them with their gifts. If you want to be funny about it, go ahead and get down on one knee!

  1. Create "wanted" signs

Create a "Wanted: Groomsman" or "Wanted: Best Man" sign with each guy's photo and the wedding details. You can find cool templates online or work with a designer on Etsy (or a local graphic designer). Some of these signs are designed to attach to a bottle of booze, so you should have a little less convincing to do! 

  1. Design themed shirts for the guys to wear under their suits

Not only will this idea unify the group, but it'll also make for some super cool photo ops! You can choose the theme based on your personal or individual interests. Choose your favorite superheroes, bands, sports teams, or tv shows. Or, you could have everyone's names or nicknames printed on the shirts. 

  1. Chug to accept

Invite the guys over for a backyard BBQ and present them with personalized coolers from Groovy Groomsmen Gifts. The coolers come with a removable sticker that says "chug to accept," so be sure to stock them with something they'll like to drink! Then, they can remove the stickers and enjoy the beer coolers for years.

  1. Help them pack with custom toiletry travel companions

If the wedding will require travel, help the guys pack. Groomsday makes a toiletry travel companion that can be customized with the favorite colors & initials of your groomsmen.

  1. Flasks, but make them funny

ToonedUpGifts on Etsy can hook you up with the best flasks ever! Have each groomsman's caricature and "Groomsman" title placed on stainless steel flasks. You'll also receive a digital image of each image to share on social media. So drink up and laugh for hours at each other's hilarious cartoon photo flasks. 

  1. Socks

It might not sound complicated, and that's because it's not. Consider fancy or funny matching socks if you want to give your groomsmen a budget-friendly proposal gift. You can also get them personalized for the groom, Best Man, and groomsmen. Keep their feet warm while they try to keep yours from getting cold! 

  1. Take them camping

Plan a weekend trip for your closest buddies and give them a thoughtful camping pop-up card with a message, "Happy trails, then tuxedo tails." Or a clever message of your own. This bonding time will be a great time to start looking forward to the wedding, making bachelor party plans, and enjoying adventures outside everyday life. 

  1. Talk about the time 

The author Leo Christopher said, "There's only one thing more precious than our time, and that's who we spend it on." Do you agree? Share the quote in a notecard asking each friend to be a groomsman; then, give each guy a wooden watch from Modply. These watches can be engraved with each groomsman's name and the wedding date.

  1. "Wood" you be my groomsman? 

One handmade shop in Tulsa, OK, the super classy TwoGuysBowties, makes the coolest Wooden bowties, wood-embellished pocket squares, and unique wooden lapel flowers. With a nice variety of styles, give each groomsman a different piece when you ask, "'Wood' you be my groomsman?" Find them on Etsy! Then, write a note about your friendship & pop the question on the back of a personalized postcard from Zazzle.

  1. Custom labels for literally anything

Find adorable custom labels for cigars, beer cartons, socks, or whatever other gifts you think would be perfect for giving your buddies. If you decide to put a creative label on any form of beer, write a message inside this pop-up beer card to ask the guys: "Will you beer my groomsman?" or "Will you beer my best man?" Of course, we recommend a different approach when you propose to the ring bearer. 

  1. Help cover the cost 

Maybe we should have put this at the top of this list, but if you want to save time and energy instead of spending it on groomsmen's proposals, offer to cover the cost of the groomsmen's suits or tuxes or travel costs. Of course, if you suggest helping with their expenses, you will undoubtedly receive a resounding yes from the get-go! 

Groomsmen Proposal Messages

What can you say or write in a card when you ask your buddies to be in your wedding party? You want to make the message meaningful and personal. If you can't splurge on a big gift for each guy, we recommend a Wolf Pack pop-up card or Stormtrooper Squad pop-up card to make a creative statement (and write a message inside). Here are some groomsmen proposal messages we think your friends will enjoy:

  1. Well, she said YES! So now, it's your turn. Will you be in my wedding? 
  2. I wanted to just send a text, but __________ (fiancée's name) said I had to give you this card. I am excited for you to be there on our big day! 
  3. Two words: Open Bar. Wanna be my groomsman? 
  4. You're my brother from another mother. Stand by me while I tie the knot? 
  5. I did this for you, so you don't have a choice. You're going to be in my wedding! Congrats! 
  6. Your service as a Groomsman is requested. (Or, your service is required. You choose, depending on your relationship.) 
  7. I think this might be the only choice I get to make. Will you be my groomsman? 
  8. _____________ (fiancée) said it would be "super cute" if I proposed to you. Can't wait to get hitched with you by my side. 
  9. Dust off your suit & your dancing shoes. I'm getting married, and I want you to be my groomsman!
  10. We've grown up together, and you've always been there for me. Will you be there for me when I say, "I do?" 
  11. Eat, drink, and suit up! It's time to celebrate the next stage of my life, and I want you to be by my side. 
  12. I need someone to give a funny speech at my wedding, so will you be my Best Man?
  13. Will you join my Wolf Pack as my groomsman? Howl appreciate it! 
  14. This isn't a drill. I'm getting married & I need you there! Will you be my groomsman? 

Bridesmaids & groomsmen make the wedding planning and events go smoothly. The right attendants will make your wedding go off (mostly) without a hitch! Not to mention, having your closest friends beside you on one of the biggest days of your life means the world. 

The creative way you ask them to join your wedding party will stick with them forever. Make it a story they enjoy telling. This is an opportunity to strengthen your friendship & make memories. So consider the bridesmaid & groomsmen proposals the big kickoff to your wedding season! 

Once you figure out how you want to ask your bridesmaids and groomsmen, the next step is to find a perfect card. There are lots of unique and artistic choices in Lovepop's Wedding Collection. Once you choose the card, decide what to write in your bridesmaid proposal card & think of the perfect proposal messages for your groomsmen. Then, with a creative proposal and memorable card, your wedding party will be thrilled to support you. Happy proposing & celebrating! 

 

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