On your wedding day, you know who you want by your side. Now is the time to ask them to serve as your best men at your upcoming wedding. We’ve witnessed a rise in the number of full-blown wedding party proposals recently.

When it comes to asking your friends and family to participate in your wedding, couples are getting more creative—and we’re here to show you how to do the same.

Listed here are some of the most creative (and well-received) ideas for a groomsmen proposal. Thanks in advance for each gentleman’s support are expressed in these cards and gifts.

Groomsmen proposal


Groomsmen Proposal Box/ Groomsmen proposal ideas

“Will you be a groomsman for me?” coupled with a gift set full of treats, it sounds even better. If you don’t have a lot of time to go all out on gifts for your guys, these proposal boxes are a great option.

Assorted “Cheers” Gift Packages

A proposal gift box for the groomsmen

With this groomsmen proposal box, you can go big or go home. Everything you need to celebrate your big day is included in the box, including a “cheers” cup, a cigar cutter, an insulated bottle opener, and sunglasses for the groom.

When they open it, they’ll know what it’s for and get excited about the big event.

Wedding box are available for $34 apiece.

Boxes of Proposal for Groomsmen Customized

Personalized proposal box for the groomsmen

You can personalize these gorgeous wooden boxes, which read “Your service is requested,” with their names. You get to choose the tiny liquor bottle to go with each groomsmen’s proposal present, which includes a whiskey glass and shot glass inside.

For $50 per, David’s Bridal offers a personalized spirit gift box set with shot glasses inside.

Gift Sets for Groomsmen’s Accessories

A proposal tie box for the groomsmen

Is there a foolproof groomsmen proposal idea? They’ll be able to use this tie and pocket square for years to come. This set includes a matching tie bar as well. Add a “suit up” card to the groomsmen’s proposal box.

Purchase a $50 gift set for yourself!

Proposal package with a flask and a watch

You can’t go wrong with this stylish pair: a matching flask and black watch. It’s a brilliant method to let them know it’s time to toast. (Have you figured it out yet?)

Watch and hip flask set, $51 each.

Boxes for Golf Groomsmen gifts to Propose with in wedding party

Proposal box for golfing best groomsmen

As a “will you be my personalized groomsmen?” present, this package includes a personalized golf ball and an amusingly-named golf tee. The best man proposal is also available if you’re planning a separate proposal.

Seller offers golf-themed best man and groomsman proposals for $7 per package of cards.

Gifts for the Groomsmen as a Proposal Present/groomsmen proposal box

You can, of course, pick separate gifts for the groomsmen (or best man) in your life. As spectacular as these gifts still are, they’re the perfect mementos for this one-of-a-kind occasion.

Mugs with a baseball bat on the side

Proposal gift: a baseball bat mug for the best groomsmen

These mugs are fashioned as baseball bats! Isn’t that amazing? Personalize each one, such as “Will you be my groomsman?” by having it engraved. For a group of sports-obsessed guys, this is an ideal proposal present.

Made-to-order Dress groomsmen proposal Sock

Personalized socks for the guys as a proposal groomsmen gift that resembles a wedding title

Itching feet? It’s a no-brainer with these socks for groomsmen gift. “Will you be my groomsman?” is the question printed on the label of each pair.

A variety of colors and patterns are available for this proposal idea. Wearing them on their wedding day will earn them extra points.

Get them that proposal idea wedding title with a personalized label and wedding fashion touch.

Personalized socks

Puzzles for the groomsmen proposal ideas

Personalize your groomsmen proposal ideas by thinking outside the box. “[Groomsman’s name], your assistance as a groomsman is required— [groom name].” Send the parts to each person to place together and discover the message.

Will You Be My Best Man Gift Puzzle $6 each?

Custom Watches for the Pocket

Personalized pocket watches falls under the man’s wardrobe collection for the groomsmen proposal gift as a proposal at the bachelor party

They’ve been there for you every step of the way, so these personalized pocket watches are a subtle reminder of that.

The monogrammed timepieces will make your friends feel even more handsome on an important day.

Travel Toiletry Bags

Some of the best groomsmen proposal gifts are the most practical—and this is especially true on the big day.

Get them set for the dressing room with these personalized Dopp kits wedding title

Ingenious Cufflinks with a Personality

Groomsmen proposal gift: bourbon barrel cufflinks custom made

These cufflinks are a standout among the rest of the groomsmen proposal gifts. They are made from bourbon barrels because that is where the wood comes from.

After all, the groomsmen proposal box should be just as memorable as the occasion itself.

 Bourbon barrel cufflinks custom made

Fisherman’s Specialty Lures

Groomsmen proposal gift ideas: personalized fishing lures

Honor their interests with a groomsmen proposal gifts for your groomsmen.

These “groom,” “best man,” and “groomsman” fishing hooks are perfect for your next outing to the lake with your best friends’ family members!

Personalized fishing lures

Knives Designed by You

Proposal gift: personalized fishing lures for the groomsman proposal card

It comes with a fire starter and LED torch, so they’ll be prepared for anything. This proposal presented for the groomsmen shouts “bachelor party camping.”

Personalized pocket knives with lights are $20 each.

Personalized fishing lures

Beer Mugs That Make You Laugh

Proposal present for the personalized groomsmen proposal: a custom beer cup

You might use your sense of humor to show how much you care. You might like these “great brains drink similar” beer mugs if that is the case for you. Because your wedding party is made up of only the best.

Large glass beer mugs are $9 per.

 A custom beer cup

Proposal Coolers for Groomsmen(groomsmen proposal ideas)

Groomsmen gifts for the proposal-gift box

“You have to be my groomsman for the…” is written on the box of these drink sleeves. There are “brews and the I Do’s” printed on the sleeves.

They’re all the fun and budget-friendly choice for the groomsmen proposal idea.

Coffee Mugs Personalized

Proposal gift for groomsmen: a personalized coffee mug

The drinkware that groomsmen present to the bride and groomsmen do not have to be tied to drinking. Coffee aficionados and those who prefer to camp will enjoy these thermally insulated camp mugs. For the wedding, they’ll encourage the males to get pumped up and ready to go.

The proposal idea is available for purchase for a total of $28.

Coffee mugs personalized

Weekender Bags with a Personal Touch

This is a custom gym bag for men’s wedding proposal gifts

Using these bespoke duffles for the bachelor party and the wedding day will be a huge help. Inquire about their interest in joining you on your “next big adventure” by sending them a note.

Every weekender bag costs $20.

Do you have what it takes to be my best man?

Weekender bags with a personal Touch

For the groomsmen proposal idea, a wooden bowtie

This artist creates wacky wooden bow ties for groomsmen proposal that are packaged as gifts. This cowboy boot-inspired design is ideal for a raucous Southern or Western gathering. The clips can be worn, but they can also be kept as a memento.

Gifts for the groomsmen proposal: $25 apiece for Rustic Love and Wood country bow ties.

Proposal Cards for the Groomsmen proposal

Send out a proposal card with each of your groomsmen’s gifts, or give them out on their own. Both options are OK!

The Groomsmen Proposal gift Feature Mustaches

Groomsmen Proposal card with a mustache for the groomsmen

Tell them you’ve got a mustache and ask if they’ll be your best man. Using the provided fake facial hair, they are encouraged to pose for a picture with the groom and send it along with the card.

Groomsmen proposal card tarting at $5 per.

Groomsmen Proposal Cards That Say “Suit Up”

Proposal card for the groomsmen: Suit Up

These straightforward cards read, “My brother. It’s all over now. Get ready. Do you want to be my best man?”

For $13 a set of 10, you can have Forever Studio groomsmen proposal card.

Proposal Cards for Groomsmen with a Twist

Proposal card for the groomsmen proposal

With an open bar at your wedding reception, you can bribe them just a bit. Make it clear that you’re inviting them to a “grand celebration” and that you want to offer them a unique role.

From $4 per card, Mrs. Case’s shop, Will You Be My Groomsman or Best Man

Groomsmen Proposal gift Inspired by Hogwarts

A Harry Potter-themed proposal card for all the guys

Have a bunch of Potterheads you’d like to buy? “Mischief will be managed—would you be my groomsman?” is the message on these groomsmen proposal gift. A Harry Potter-inspired typeface.

Mrs. Case’s Shop Is There a Groomsman or Best Man for My Wedding? Is selling Harry Potter-themed cards for as little as $4 apiece.

Proposal Scratch-Off Tickets for Groomsmen gift ideas on wedding day

Proposal lottery tickets for the groomsmen proposal gifts

Be sure to tell them how lucky they are to have been chosen as one of your guests. You and your future groomsman or best man can design these lottery ticket-inspired cards with your picture and the question “Will you be my best man?” What about serving as a groomsman for me?

Wedding party scratchers will set you back $4 each.

Spiral Groomsmen Proposal

Put a little gridiron in your gifting with a gift that won’t fumble on your big weekend. Your groomsman will feel like a Super Bowl MVP when you toss your groomsmen a perfect spiral with this cool personalized football. How many gifts can you ask your man to run a deep slant to receive? Throw some laces in his hand with a gift that won’t disappoint.

This idea is social distance friendly and an especially good groomsmen proposal idea if any of you guys are freaked out by Covid and does not want to get anywhere near you.

To pull this groomsmen proposal idea off on the same page, do the following:

Chug beer

Put the labels and photographs below on one of their favorite brews, and force them to drink it if they accept your invitation to be in your wedding party as a groomsman or best man. This groomsmen proposal idea can be pulled off in person with your group, or it can be sent to them via mail. Enjoy life’s biggest moments in the sporting event of chug beer and other third party products since its a lifetime event for all potential groomsmen

Proposal for a beer label from the groomsmen

Do the steps to pull off this groomsmen proposal:

A bonus: Once you’ve got a video of everyone, combine them all into one film that you can distribute to everyone and cherish as a memento forever.

Have fun with it and tag us in the video on social media.


To begin brainstorming ideas for a groomsmen proposal, keep it simple. Send a card asking, “Will you be my groomsman?” You can do better than a simple notice with names, dates, and a request for a groomsman.

Make your card stand out with a little flair. Assume that your groomsmen will accept the “ball and chain,” and send them a “your mission” card. Make it appear as if it is being sent to a covert operative.

Alternatively, you could send them a card with step-by-step instructions on how to knot a tie. While they’re with you, they’ll have to put their best foot forward. “I found my wife, but I’ll always need my lads” is always a safe bet if you prefer a more straightforward approach.

Most of the time, simple approaches are the greatest ways to invite your groomsmen to be part of your big day.

Incorporate a second step by including event tickets. A concert, a poker night, a wine tasting tour, or a short road trip are all excellent ideas.

A night or weekend out to enjoy the camaraderie of being a Groomsman or Best Man is highly suggested. As a special thank you, or as a way to “pop the question” to your groomsmen, you can provide this great gift on the wedding date.

Some outstanding beer-themed groomsmen proposal ideas are needed to round out this list. Even though event-based groomsmen proposals might be great, adding some memorabilia to the occasion gives it that little extra punch that most grooms are looking for these days.

An etched beer mug is a popular accompaniment to this type of proposal. It is possible to incorporate a few of the names of the bride and groom as well as a date and place on a groomsmen engraver.

A personalized bottle of beer or spirit or pint glass can also benefit from these details. Beer or whiskey that has been made especially for you is a special treat that will always be appreciated.

A liquor bouquet is a great way to show your men how much you appreciate them.

Although gender stereotypes might be slippery ground, we’re convinced that most groomsmen would prefer a sample-sized assortment of vodka and cognac to the genuine thing during the one knee event.

It is always a pleasant surprise to see these liquor bouquets on display. You can guarantee that a surprise delivery to his home or business will bring a grin of bonus points on his face and make him remember it.