Asking the Boys: 17 Creative Groomsmen Proposal Ideas

Updated on March 02, 2023 by Chris Bajda

So you're tying the knot and need to ask your boys to stand by you on your big day?

Look at you, all grown up and getting hitched. But let's be real, asking your best buds to be your groomsmen can be a tough task. Do you go with the standard text message? Nah, too boring. Maybe a singing telegram? Too corny.

Fear not, because we've got some comically genius ideas to make your groomsmen proposal unforgettable. Get ready to laugh, cry, and maybe even cringe a little as we take a dive into the wacky world of groomsmen proposals. Let's do this!

Read on to find the creative ways to win your groomsmen's hearts!

1. Pop The Proposal Bottle Opener

If you want a memorable way to ask your groomsmen to stand by your side on your special day, then these Pop The Proposal Bottle Opener groomsmen proposal gifts are perfect.

These groomsmen proposal ideas fit in any wallet or pocket and has a custom message etched into the stainless-steel surface.

This unique groomsmen gift makes your groomsmen's proposal even more meaningful!

2. Groomsmen Proposal Gift Box

One of the most popular ways to ask your groomsmen to be a part of your special day is with a Nana Studio Groomsmen Proposal Gift Box.

A groomsmen proposal gift box contains a personalized mug, wedding socks, a wooden bow, a foam rose, sunglasses, and raffia.

This groomsmen proposal box is usually decorated with the groomsmen's name or a wedding date they can keep as a memento of your wedding day.

3. Wooden Proposal Card

Wooden Proposal Card is a thoughtful and unique way to ask your groomsmen to stand by your side on the big day.

One famous example of these groomsmen proposal ideas is, "This could have been a text but she made me do it," which is a humorous way to get your friends involved in the bachelor party.

This groomsmen proposal gift can be made of cherry wood or any other type of wood, depending on your preference.

4. Basketball Personalized Tickets

Personalized Basketball Ticket can be a great way to ask your groomsmen to stand with you on your special day.

These best groomsmen proposal gifts are a perfect way to commemorate the day you asked them to join your wedding party.

Add the personalized wedding titles inside the ticket and include a groomsmen gift to make it even more meaningful.

5. Survival Groomsman Proposal Set

Make your groomsman feel ready for anything with a Survival Groomsman Proposal Set!

This groomsmen proposal box includes 14 tools in one and comes in a waterproof and durable case, so you don't have to worry about any of the contents getting damaged or wet.

This groomsmen proposal idea is excellent if your groomsmen are outdoorsy or enjoy camping and hiking trips. 

6. Groomsman Proposal Video

Proposal Video is a unique and creative way to ask your groomsmen to be part of your special day.

Digital downloads are the best way to make a groomsmen proposal video because it makes it easier for your groomsmen to share their reactions with their friends and family.

Your groomsman proposal gift video should be something special that reflects the bond between you and each of your groomsmen.

7. Chug to Accept Koozie

Chug to Accept Koozie is a great way to propose to your groomsmen!

This groomsmen proposal idea features double-walled vacuum insulation with a powder-coated finish and is made with quality stainless steel.

The groomsmen proposal gift also has an amusing phrase on the front, "Chug to Accept," so everyone will know exactly why you are offering this classy gift.

Related: 19 Funny Beer Koozies That Will Keep Your Friends Laughing (and Your Beer Cold)

8. Groomsmen Proposal Acrylic Plaque

Surprise your groomsmen with a unique and meaningful way of asking them to be part of your wedding party.

An Acrylic Plaque groomsmen proposal gift is an ideal way to show appreciation and gratitude for their friendship.

And what better way to say "I can't say I Do without you" than with these Best Groomsmen Proposal Gifts?

9. Custom Groomsmen Socks

If you want a unique way to propose to your groomsmen, why not consider Custom Photo Socks?

These groomsmen proposal socks are the perfect way to personalize your proposal and make it stand out for destination wedding.

Whether you print your best man's face on the socks or include your own personal message, this groomsmen proposal idea will surely be appreciated by your groomsmen.

Related: Best Groomsmen Socks

10. Groomsmen Cufflinks

Groomsmen Cufflinks are the perfect way to add a touch of class and sophistication to his wedding attire.

These groomsmen proposal ideas are an elegant way to show appreciation for your future groomsmen and help them look their best on your special day.

This groomsmen proposal box is an excellent way to show appreciation for your groomsmen's role in your wedding party and make a lasting impression you will treasure for years.

11. Video Game Funny Proposal Card

Are you looking for a unique way to ask your groomsmen to be part of your wedding day? This fun, playful Video Game, groomsmen proposal idea will surely win them over!

These groomsmen proposal ideas feature a video game controller design with the phrase "Game Over She Wins," perfect for your groomsmen proposal.

This unique groomsmen proposal card will show your groomsmen how much you appreciate them and how much they mean to you.

12. Personalized Engraved Hip Flask

For a truly classic and timeless groomsmen proposal idea, why not go for a Personalized Engraved Hip Flask? It will surely be appreciated by your groomsmen and will serve as a reminder of your special day.

These groomsmen proposal ideas can be personalized with your choice of wedding title or name, making it the perfect way to ask your groomsmen to be part of your wedding day.

This proposal gift has a classic design that will stand the test of time, perfect for a unique souvenir from your bachelor party.

13. Groomsmen Cigar Box

Groomsmen Cigar Box is a great way to propose to your groomsmen!

This groomsmen proposal gift box comes in various colors, making it the perfect option for any groom. It has a personalized engraving on the box, and you can fill it with two special cigars for each groomsman.

Your future groomsmen will be impressed with the thoughtfulness of your gesture, and it will be something they can keep forever.

Related: 23+ Unique Custom Cigar Boxes to Show Off Your Smoke

14. Groomsmen Beer Mug

Groomsmen Beer Mug is a great way to propose to your groomsmen in a fun and creative way.

These groomsmen proposal ideas are a fun way to thank them for their help and loyalty and to show them that you appreciate their friendship.

This groomsmen proposal idea is 22 ounces of fun, made with a sturdy wooden material that will last years.

15. Groomsman Scratch-off Card

It is an excellent idea for groomsmen proposals because it's simple, fun, and creative. You can make a Scratch-off Card from scratch or purchase one from an online store.

When your groomsman reveals the message beneath the scratch-off card, it will surely make them smile.

To make these groomsmen proposal ideas even more unique, you could include some small tokens that they can use to commemorate the occasion.

16. Whiskey Decanter

When looking for a unique way to propose to your groomsmen, consider giving them a Personalized Whiskey Decanter.

This groomsmen proposal gift is an elegant and stylish way to show appreciation for their friendship and ask them to be part of your special day.

This groomsmen proposal box holds 32oz of your favorite whiskey, while the accompanying rock glass holds 5oz.

Related: 17 Unique Whiskey Decanters That Will Up Your Drinking Game

17. Pocket Watch

If you want to give your groomsmen a timeless gift, consider a Pocket Watch.

This groomsmen proposal gift was once a traditional accessory for gentlemen and were often given to commemorate a special occasion.

These groomsmen proposal ideas are a classic way to show appreciation for the important men in your life.


47 Badass Groomsmen Gift Ideas


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