29 Creative Groomsmen Proposal Gifts and Ideas

December 13, 2023 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!

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

2. Time to Suit Up Gift Box

TheTime to Suit Up groomsmen proposal gift is a thoughtfully curated box set, perfect for extending a special invitation to your groomsmen. 

This unique groomsmen gift set includes a custom low-ball glass, a 4 oz. premium soy candle with a masculine scent, maple bourbon flavored toothpicks, a gold credit card style bottle opener, playing cards, and a custom liquor label (alcohol not included). 

The box and contents can be personalized, making it a unique and memorable way to ask your friends to be part of your wedding.

3. Mustache Groomsman Proposal Box

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.

4. Man of the Hour

TheMan of the Hour groomsmen gift box set is an all-inclusive package for your wedding party. 

This groomsmen proposal gift box set includes a matte black flask, a sleek knife, a functional wallet with RFID blocking protection, and a stylish black humidor box. Each item offers both practicality and elegance, making it a perfect way to honor your groomsmen. 

The box and contents can be personalized for each groomsman, adding a unique touch to this thoughtful gift.

5. Paul Bunyan Gift Box

ThePaul Bunyan Gift Box is a rugged and unique groomsmen proposal set. It includes an ax, a shot glass, and a personalized label for a pint bottle (bottle not included). The ax, measuring 9 inches in length with a 3-inch blade, is a standout feature. 

These groomsmen gifts come in a sleek black box, which can be personalized with names and wedding details. These personalized groomsmen gifts are perfect for outdoorsy and adventurous groomsmen.

Related: Delight your groomsmen with our specially curated collection of groomsmen gift boxes, perfect for showing your appreciation in style.

6. Food, Booze, Cake, Girls Proposal Card

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.

7. Baseball Groomsmen Proposal

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. Groomsmen Group Chat Proposal Wallet

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.

9. Personalized Football

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.

10. Coolest Proposal

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.

11. Groomsmen Proposal Golf Ball Proposal

TheGroomsmen Proposal Golf Ball Proposal is a charming and sporty way to invite your groomsmen. It includes a customizable golf ball, which can be engraved with up to three lines of text, offering options like name, title, or date. 

The set also comes with a gift box, personalized lid, and display insert. You can add a tee for a complete golf-themed proposal.

Related: Swing into style with our collection of golf-themed groomsmen gifts, perfect for those who love the green.

12. Custom Call of Duty Inspired Proposal Card

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.

13. Groomsmen Proposal Ticket - Golf

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.

14. 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.

15. 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.

16. 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.

17. Survival Groomsman Proposal Set

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. 

18. 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.

19. 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)

20. 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?

21. 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

22. 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.

23. 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.

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

25. 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. It makes great bachelor party favors!

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

26. 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.

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

27. 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.

28. 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

29. 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.

More Groomsmen Proposal Ideas

When it comes to proposing to groomsmen, creativity can go a long way.

Here are some fun ideas that will get your friends excited about being part of your big day.

The Classic Beer Proposal

For the beer-loving groom, a classic beer proposal is always a hit. Get some personalized beer mugs or pint glasses and fill them with their favorite brew. Add a note asking them to be your groomsmen and cheers to the future.

The Sports Fanatic Proposal

For the sports fanatics in your life, consider proposing with tickets to a game or a personalized jersey. You could also get creative with a sports-themed gift basket filled with snacks and gear. Don't forget to include a note asking them to be a part of your team.

The Adventure Seeker Proposal

For the groomsmen who love the outdoors, consider proposing with a camping or hiking trip. You could also get them personalized water bottles or backpacks with a note asking them to join you on your wedding adventure.

The Foodie Proposal

For the foodies in your life, consider proposing with a personalized cookbook or a gift card to their favorite restaurant. You could also get creative and put together a food-themed gift basket with their favorite snacks and treats. Add a note asking them to be your foodie partner in crime.

The Gamer Proposal

For the gamers in your life, consider proposing with a new game or a gaming-themed gift basket. You could also get them personalized gaming controllers or headsets. Add a note asking them to be your player two on your wedding day.

Remember, the most important part of proposing to your groomsmen is to make it personal and fun.

Customizing Your Proposal

When it comes to proposing to your groomsmen, the possibilities are endless. Why not get creative and customize your proposal to make it extra special? Here are some ideas to get you started:

  • Personalized Gifts: Everyone loves a thoughtful gift, so why not personalize it to make it even more special? Consider getting each groomsman a customized flask, a monogrammed watch, or a personalized beer mug.

  • Inside Jokes: If you and your groomsmen have a lot of inside jokes, why not incorporate them into your proposal? For example, you could create a scavenger hunt that includes clues that only your groomsmen would understand.

  • Favorite Things: Show your groomsmen how much you appreciate them by incorporating their favorite things into your proposal. If one of your groomsmen loves cigars, for example, consider getting him a personalized cigar cutter.

  • Unique Experiences: If you're looking for something really special, consider giving your groomsmen a unique experience. This could be anything from a day of golfing to a weekend getaway.

No matter how you choose to customize your proposal, the most important thing is to make it personal and heartfelt. Your groomsmen are some of the most important people in your life, so take the time to show them how much they mean to you.

Avoiding Proposal Pitfalls

Groomsmen proposals can be tricky to navigate. While it's important to make your groomsmen feel special and appreciated, it's also easy to fall into some common proposal pitfalls.

Here are a few tips to help you avoid them:

1. Managing Expectations

Firstly, don't assume that everyone will say yes. While it's tempting to ask all of your closest friends to be your groomsmen, it's important to remember that not everyone will be able to commit. Be prepared for the possibility of some rejections, and don't take it personally if someone declines.

2. Keeping It Real

Secondly, don't put too much pressure on your groomsmen. While it is great to have a fun and creative proposal, don't make it so elaborate that your friends feel obligated to say yes. Keep it simple and sincere and remember that the most important thing is the friendship you share.

3. Financial Consideration

Thirdly, don't forget to consider your budget. Groomsmen proposals can quickly become expensive, especially if you're planning on giving gifts or hosting a celebration. Set a budget and stick to it, and don't feel like you need to go overboard to impress your friends.

The Aftermath of The Proposal

Now that the groomsmen have been successfully proposed to, what's next? The aftermath can be just as important as the proposal itself. Here are a few things to keep in mind:

1. Give Them Time to Respond

It's important to remember that not everyone will be able to say yes right away. Maybe they need to check their schedule, talk to their significant other, or just take some time to think about it. Don't be too pushy or demanding. Give them the time and space they need to make a decision.

2. Be Prepared for Some Rejection

Unfortunately, not everyone will be able to be a part of the wedding party. Maybe they have other commitments or just don't feel comfortable with the role. Whatever the reason, don't take it personally. It's better to have someone decline than to have them feel obligated and unhappy.

3. Keep Them Involved

Once the groomsmen have accepted the proposal, it's important to keep them involved in the planning process. Make sure they know what's expected of them and when. Keep them updated on any changes or updates. And don't forget to show your appreciation for their help and support.


Explore our exclusive selection of groomsmen gifts to find the perfect way to thank your wedding party.

Discover the ideal way to ask your best man with our curated collection of unique and thoughtful proposal gifts.

Browse our top-rated collection of best man gifts, each thoughtfully selected to honor your right-hand man on your big day.

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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