37 Creative Groomsmen Proposal Gifts and Ideas

Updated on May 29, 2024 by Chris Bajda

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. 

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 world of groomsmen proposals. Let's do this!

For Adventurous Spirits

1. Ultimate Groomsmen Proposal Set

Price: On Sale for $79.99

Create an unforgettable proposal with the Ultimate Groomsmen Proposal Set.

This comprehensive gift box includes a personalized wooden watch, a tactical pen with multiple functions, a triple torch lighter with a built-in cigar rest, and a sleek wallet. Each item is beautifully crafted and personalized, all housed in a custom wooden box lined with Spanish cedar.

Perfect for expressing your appreciation and making your proposal truly special, this set ensures your friends feel honored and excited to join you on your big day.

2. Survival Groomsman Proposal Set

Price: $39.99

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

This groomsmen proposal survival gift 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. 

3. Custom Proposal Axe

Price: $39.99

Ask your best buds the most important question with the Custom Proposal Axe.

This personalized battle axe features your friend's name on the handle and a special message on the blade. It's a unique and badass way to invite them to be your groomsmen. Crafted with a durable stainless steel blade and available in multiple handle options, this axe is both a memorable keepsake and a functional tool.

Perfect for making your proposal truly unforgettable and showing your appreciation in a distinctive way.

For Sports Lover

4. Golf Ball Proposal Box

Price: $14.99

Add a fun twist to your groomsmen proposal with the Golf Ball Proposal Box.

This unique set features a practice golf ball and a witty message, inviting your friends to "PAR TEE" and join you on your big day. The box pops open to reveal a personalized note and the practice ball, making it a playful and memorable way to ask your groomsmen to stand by your side.

Perfect for golf enthusiasts, this box combines humor and heartfelt sentiment.

5. Groomsmen Proposal Ticket - Golf

Price: Starting at $9.99+

TheGroomsmen Proposal Ticket - Golf is a creative way to invite your groomsmen with a golf-themed ticket. These personalized Masters-style tickets can be customized with wedding details and roles. 

You can choose between a digital copy for home printing or physical tickets in medium gloss or premium matte. They are perfect for golf enthusiasts and add a classy touch to your groomsmen proposals.

6. Personalized Football

Price: $34.99

ThePersonalized Football is an ideal gift for football enthusiasts in your wedding party. 

This genuine Rawlings Official League OLB3 football comes in three sizes and features a white top with a traditional football bottom. It can be custom engraved with three lines of text, allowing for personalization with names, dates, or special messages. 

The warm brown engraving contrasts beautifully against the ball, making it a standout sports-themed groomsmen gift.

7. Baseball Groomsmen Proposal

Price: $16.99

TheBaseball Groomsmen Proposal is a unique and sporty way to ask your friends to join your wedding party. These best groomsmen proposal gifts feature real Rawlings Official League OLB3 baseballs, which can be engraved with a custom message like "Suit up, will you be my groomsman?" 

You can choose between a tuxedo or a bowtie design, making it a personalized and memorable proposal for any baseball enthusiast.

8. Basketball Personalized Tickets

Price: Staring at $9.99+

A 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.

For Drink Enthusiasts

9. Coolest Beer Cooler

Price: $44.99

TheCoolest Proposal is a fun and functional cooler gift set. This 600-Denier Polyester cooler, with a PEVA (PVC free) lining, can hold up to 12 bottles or 18 cans. It features an adjustable shoulder strap, a front storage pocket, and a side bottle opener. 

This groomsman proposal gift can be personalized with two initials and is ideal for events like tailgating and BBQs. Upon receiving, groomsmen can find a label inside, making it a unique proposal gift.

10. Pop The Proposal Bottle Opener

Price: $12.99

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. It makes your groomsmen's proposal even more meaningful!

11. Groomsman Proposal Video

Price: $9.01

A 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.

12. Chug to Accept Koozie

Price: $19.99

A 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)

13. Personalized Engraved Hip Flask

Price: Starting at $12.52+

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

14. Groomsmen Beer Mug

Price: Starting at $31.34+

A 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.

It is 22 ounces of fun, made with a sturdy wooden material that will last years.

For Cigar Lovers

15. Classic Cigar Proposal Gift Box

Price: $79.99

For the cigar-loving gentlemen in your life, this luxurious proposal groomsmen gift box is the ultimate way to ask them to stand by your side. Featuring premium cigars, a sleek cutter, and a personalized lighter, this set is designed to impress and delight.

Perfect for creating an unforgettable and classy proposal moment, it’s a gift your friends will truly appreciate and enjoy.

16. Cigar Travel Case with Flask

Price: $34.99

Combine style and convenience with this Cigar Travel Case with Flask, the perfect proposal gift for your groomsmen.

Featuring a durable case for their favorite cigars and a built-in flask for their preferred drink, this gift is ideal for the discerning gentleman. Propose in a sophisticated way that ensures your friends will feel appreciated and ready to celebrate with you in style.

17. Groomsmen Cigar Box

Price: $7.99

A 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. It makes great bachelor party favors!

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

For Gaming Enthusiasts

18. Custom Call of Duty Inspired Proposal Card

Price: $30.00

TheCustom Call of Duty Inspired Proposal Card is a unique and playful groomsmen proposal idea, especially suitable for video game enthusiasts. 

This thoughtful groomsmen proposal gift replicates a Call of Duty game cover, tailored to your wedding details. It allows personalization of the bride and groom's names, wedding date, state, and recipient's role and name. 

These best groomsmen proposal ideas offer a fun twist on traditional groomsmen proposals, combining a beloved video game theme with wedding festivities.

Alongside this option, you can also find a variety of other game-themed proposal DVD covers:

These diverse options cater to different gaming preferences, adding a fun and personalized touch to your groomsmen proposals.

19. Video Game Funny Proposal Card

Price: $5.20

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.

Proposal Gifts as Wedding Day Accessories

20. Bowtie Groomsmen Proposal

Price: $14.99

It's time to suit up! This stylish proposal card comes with a bowtie for your groomsmen to wear on your wedding day.

Invite your best friends to stand by your side with this classy and thoughtful gesture, ensuring they look as sharp as the occasion. They’ll love the personalized touch and the opportunity to dress to impress.

Related: Easy Shop Men's Accessories for any Occasion! 

21. Time to Suit Up Gift Box

Price: $59.99

It's time to suit up! This elegant gift box includes a stylish watch, a sleek wallet, and a heartfelt groomsmen proposal card.

Perfect for asking your friends to stand by your side on your big day, this gift set combines practicality with a touch of class, ensuring they'll feel appreciated and excited to join the celebration.

They’ll value this thoughtful gift and the special role they’ll play.

22. Custom Groomsmen Socks

Price: $27.00

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

23. Groomsmen Group Chat Proposal Wallet

Price: $39.99

TheGroomsmen Group Chat Proposal Wallet is a sleek, stylish wallet designed for the modern groomsman. Made from a combination of aluminum, wood, and stainless steel, this groomsmen proposal idea features a money clip and RFID protection for security. 

The wallet, along with the keepsake box it comes in, can be personalized with names or initials. The inside of the box is ideal for a special message, making it a unique proposal gift.

24. Groomsmen Cufflinks

Price: $19.99

The 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.

25. Proposal Bi-fold Leather Wallet

Price: $24.99

Pop the question in style with this Proposal Bi-fold Leather Wallet. Crafted from premium leather, this wallet features a special message to ask your friend to be your groomsman.

Combining practicality with a heartfelt gesture, this wallet is the perfect keepsake for your big day and a lasting memento of your special bond. Your friend will treasure this meaningful and functional gift.

26. Groomsmen's Gratitude Proposal Box

Price: $44.99

Express your appreciation with the Groomsmen's Gratitude Proposal Box.

This sophisticated gift set includes a personalized wooden watch, a versatile keychain with a built-in bottle opener, and an elegant set of wooden cufflinks and tie clip. Presented in a custom pinewood keepsake box with an acrylic window, each item is meticulously engraved with your groomsman's initials.

Perfect for making your proposal both memorable and heartfelt, this box ensures your friends feel valued and excited to be part of your special day.

Groomsmen Proposal Cards

27. Funny Face Groomsmen Proposal Card

Price: $6.99

Surprise your groomsmen with a laugh and a little shock! This bold, hilarious card is packed with humor and more "F" words than they can count.

Perfect for proposing to your groomsmen in a memorable, funny, and slightly rude way, ensuring they'll never forget the moment they were asked to stand by your side. Prepare for some unforgettable reactions!

28. Indecent Proposal Card

Price: $7.99

For your best friends only! This Indecent Proposal Card uses humor and a bit of cheekiness by calling your groomsmen the "D" word, making it a perfect, funny way to pop the question.

Designed to bring out laughs and knowing smiles, this card ensures your proposal is as unforgettable as your friendship. Brace yourself for some hilarious reactions and a memorable moment they’ll never forget!

29. Uncle Sam-Themed Groomsmen Proposal Card

Price: $6.99

Uncle Sam wants YOU...to be my groomsman! This unique and humorous proposal card takes the iconic Uncle Sam recruitment poster and gives it a twist, inviting your best friends to join you on your big day.

Perfect for a fun and memorable way to ask your buddies to stand by your side, this card ensures they'll feel honored and amused by your clever proposal.

Expect some patriotic laughs and enthusiastic agreements!

30. Open Bar Groomsmen Proposal Card

Price: $7.99

Mark the date for the best party ever! This Open Bar Groomsmen Proposal Card invites your friends to join you on your big day with the promise of a great time and free drinks.

Perfect for adding a fun and enticing twist to your groomsmen proposal, this card ensures they'll be excited and ready to celebrate. Anticipate some enthusiastic responses and unforgettable memories!

31. Still Need My Boys Card

Price: $7.99

I got my girl, but I still need my boys! This heartfelt and fun proposal card is the perfect way to ask your closest friends to stand by your side on your big day.

Show your appreciation and make them feel special with this memorable invitation. They’ll be thrilled to share this special moment with you.

32. Groomsmen Suit Up Card

Price: $7.99

Suit up, gentlemen! This custom proposal card features your friends' faces on groomsmen suits, making it a fun and personalized way to ask them to stand by your side.

Perfect for a memorable and unique proposal, this card ensures your buddies will be excited to join in the celebration. Your friends will cherish this personalized keepsake and eagerly anticipate the big day.

33. Mustache Groomsman Proposal Box

Price: $14.99

TheMustache Groomsman Proposal Box offers a unique and playful way to ask your friends to join your wedding party. 

This compact 3.5" x 3.5" x 3.5" box reveals a surprise when opened, a suit image in the center and four playful statements, including a request for the recipient to wear a mustache as a sign of acceptance. 

The groomsman proposal gift box set also features a personalized name tag and black & white twine closure, adding a personal touch to your proposal.

34. Food, Booze, Cake, Girls Proposal Card

Price: $7.99

TheFood, Booze, Cake, Girls Proposal Card is a fun and humorous way to ask your groomsmen to be a part of your wedding. This personalized card captures the excitement of the occasion with its catchy phrase, reminding them of the good times ahead. 

It can be customized with the wedding name, date, and role, making it a memorable keepsake. This card is a lighthearted and charming choice for your groomsmen proposals.

35. Wooden Proposal Card

Price: $11.99

A 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.

36. Groomsmen Proposal Acrylic Plaque

Price: Starting at $30.17+

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?

37. Groomsman Scratch-off Card

Price: Starting at $3.99+

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.

RELATED: More Unique Groomsmen Proposal Ideas

How to Avoid Groomsmen Proposal Pitfalls?

When it comes to planning your groomsmen proposal, it's important to create an experience that's memorable, respectful, and enjoyable for everyone involved. Here are some common pitfalls to avoid:

1. Overly Complicated Proposals

While it's great to be creative, overly complicated proposals can become stressful and confusing. Keep it simple and focus on the sentiment rather than elaborate schemes that may go awry.

2. Lack of Personalization

A generic proposal can feel impersonal. Make sure to incorporate elements that reflect your relationship with each groomsman. Personalized cards, gifts, or messages can go a long way in showing your appreciation.

3. Ignoring Individual Preferences

Consider the preferences and personalities of your groomsmen. Not everyone may appreciate the same type of humor or style. Tailor your proposal to suit each person's taste to ensure it resonates well.

4. Overlooking Timing

Timing is crucial. Ensure you propose to your groomsmen well in advance of the wedding to give them ample time to plan and make arrangements. Avoid last-minute proposals that can add unnecessary pressure.

5. Budget Overspending

While it's tempting to go all out, remember to stick to a budget that is reasonable for you. Extravagant proposals can put a strain on your finances and may not necessarily be appreciated more than thoughtful, budget-friendly gestures.

6. Inappropriate Themes or Jokes

Be mindful of the themes and jokes you incorporate into your proposal. What may seem funny to one person could be offensive to another. Keep the tone respectful and considerate to avoid any awkwardness or hurt feelings.

7. Forgetting Practical Details

In the excitement of planning your proposal, don't forget practical details. Ensure your groomsmen know what's expected of them, the timeline, and any other important information related to their role in the wedding.

8. Neglecting a Personal Touch

Adding a personal touch to your proposal can make it even more special. Handwritten notes, inside jokes, or references to shared memories can make your groomsmen feel truly valued.

9. Underestimating Logistics

Consider the logistics of your proposal. If you're planning a surprise event, make sure all the details are well-organized and that everyone involved knows their role to avoid any confusion or mishaps.

10. Failing to Show Appreciation

Your groomsmen are taking on an important role in your wedding. Make sure your proposal expresses genuine appreciation for their friendship and commitment. A heartfelt message can make all the difference.

By avoiding these common pitfalls, you can create a groomsmen proposal that is meaningful, respectful, and enjoyable for everyone involved.

Related: More Groomsmen Proposal Gift Box Ideas

Chris Bajda

About the Author

Chris Bajda is a renowned expert in gift selection, with a 15 year history of finding unique gifts. His insight into the art of gifting and staying on top of trends by his consistent presence at major gifting trade shows, including his annual participation in NY Now trade show in New York City and several other trade shows throughout the United States. Chris has built a reputation for his knowledge in finding gifts that leave a lasting impression.



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