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Will You Be My Groomsman? 24 Groomsmen Proposal Ideas

Here's how to pop the *other* question.
Emily Platt
by Emily Platt
Updated Dec 13, 2019
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You know who you want by your side on the wedding day. Now it's time to ask them to be your groomsmen. Sure, you can just phone your guys, but lately, we've seen an uptick in full-blown wedding party proposals. Complete with funny cards and personalized gifts that really go the extra mile, couples are getting more creative with how they ask their friends and family to participate—and we're showing you how you can too. Below, shop for some of the most unique (and well-received!) groomsmen proposal ideas on the market. These notes and presents make the moment extra-memorable and say "thanks" in advance for each gentleman's support.

Groomsmen proposal ideas in this article:

Groomsmen Proposal Boxes

"Will you be my groomsman?" sounds even sweeter paired with an entire gift set full of goodies. These groomsmen proposal boxes are perfect if you rarely get a chance to go all out on gifts for your crew. 

"Cheers" Gift Sets

Groomsmen proposal gift box

If your motto is "go big or go home," this is the groomsmen proposal box for you. It comes with a "cheers" mug, a tuxedo-inspired cigar cutter, a "groomsman" koozie, a leather bottle opener and "groomsman" sunglasses. As soon as they open it up, they'll realize what it's for and get pumped for the big day. 

Kate Aspen Groomsmen Box wedding kit, $34 each, Target.com

Personalized Groomsmen Proposal Boxes

Personalized groomsmen proposal box

Get these elegant wooden boxes, which read "your service is required," customized with their names. Each groomsmen proposal gift comes with a whiskey glass and shot glass—you round it out with your choice of a mini liquor bottle.

David's Bridal personalized spirit gift box set, $50 each, DavidsBridal.com 

Groomsmen Accessories Gift Sets

Groomsmen proposal tie gift box

A foolproof groomsmen proposal idea? A pocket square and tie they can wear on the wedding day—and well beyond. This set even comes with a coordinating tie bar. Pair the groomsmen proposal box with a card that asks them to "suit up." 

BHLDN Blush Dot gift set, $50 each, TheTieBar.com

Flask and Watch Gift Boxes

Flask and watch groomsmen proposal box

Check out this dynamic duo: a sleek black watch and a matching flask. It's a genius way to tell them it's time to toast. (Get it?)

ASOS DESIGN gift watch with black hip flask, $51 a set, ASOS.com 

Golf Groomsmen Proposal Boxes

Golf groomsmen proposal box

This "will you be my groomsmen?" gift includes a customized golf ball and golf tee inside a box that (hilariously) says, "let's par-tee." If you're planning a separate best man proposal, there's also a best man version.

One19 Stationery golf best man and groomsmen proposal, from $7 per box, Etsy.com

Groomsmen Proposal Gifts

Of course, you can also opt for standalone groomsmen proposal (or best man proposal) gifts. These presents are still undeniably impressive and the perfect keepsakes for this unique moment.

Baseball Bat Mugs

Baseball bat mug groomsmen proposal gift

These mugs are made from baseball bats—yes baseball bats! How cool is that? Get each one engraved with a personalized message, like—you guessed it—"will you be my groomsman?" This is a great, go-to groomsmen proposal gift for a group of major sports fans.

Lumberlend customizable baseball bat mugs groomsmen gift idea, from $60 each, Etsy.com

Custom Dress Socks

Custom groomsmen proposal socks

Cold feet? Not a chance with these groomsmen proposal socks. Each pair comes with a personalized label that asks, "will you stand with me as my groomsman?" Choose from a mix of colors and prints. Bonus points if they wear them on the wedding day.

No Cold Feet Co Will You Be My Groomsman proposal socks and custom sock labels, from $6 per pair, Etsy.com 

"Will You Be My Groomsman?" Puzzles

Custom groomsmen proposal puzzle

Think outside the box with these personalized groomsmen proposal puzzles. Send the pieces to each guy for him to put together and uncover the message: "[Groomsman's name], your service as groomsman is required - [groom's name]." 

XOXO Kristen Will You Be My Groomsman gift puzzle, $6 each, Amazon.com

Custom Pocket Watches

Personalized groomsmen proposal pocket watch

They've been your support system around the clock, which makes these personalized pocket watches subtly symbolic. Your buddies will feel extra-dapper carrying the monogrammed timepieces on the big day.

The Knot Shop personalized gold frame gunmetal pocket watch & fob, $30 each, TheKnotShop.com 

Travel Toiletry Bags

Groomsmen proposal gift custom toiletry bag

Some of the best groomsmen proposal gifts are the most useful—and especially when the big day rolls around. Get them prepped for the getting-ready suite with these cool, personalized dopp kits.

The Knot Shop personalized men's hanging travel toiletry bag, $20 each, TheKnotShop.com 

Custom bourbon barrel cufflinks groomsmen proposal gift

Cufflinks are classic groomsmen gifts, but these stand out from the pack. That's because the wooden accessories are crafted from bourbon barrels. After all, groomsmen proposal gifts should be as special as the occasion. 

Donald J. Fuss groomsmen gift cufflinks crafted from a bourbon barrel, $45 per pair, Etsy.com 

Personalized Fishing Lures

Custom fishing lures groomsmen proposal gifts

Honor their hobbies with your groomsmen proposal gift. You can use these "groom," "best man" and "groomsman" fish hooks on your next group trip to the lake. 

Moe's Handcrafted personalized usable groom, groomsman or best man fishing lure, $13 each, Etsy.com 

Custom Pocket Knives

Custom pocket knife groomsmen proposal gift

They'll feel prepared for anything with this handy survival knife, which comes with a fire starter and LED flashlight. This groomsmen proposal gift screams "camping bachelor party."  

The Knot Shop personalized black & silver pocket knife with light, $20 each, TheKnotShop.com 

Funny Beer Mugs

Custom beer mug groomsmen proposal gift

Maybe you express your love with your sense of humor. If that's the case, try these fun "great minds drink alike" beer mugs. Because only the greatest made it into your wedding party. 

The Knot Shop personalized large glass beer mug in Great Minds Drink Alike engraving, $9 each, TheKnotShop.com

Groomsmen Proposal Koozies

Koozie groomsmen proposal gift

These drink sleeves come in a box that says, "you have to be my groomsman for the…" The sleeves themselves say, "brews & the I Do's." They're a playful and affordable option for the groomsmen proposal.

Everly Grayce groomsmen proposal Will You Be My Groomsman Brews and I Do's can coolers, $10 each, Amazon.com 

Custom Coffee Mugs

Custom coffee mug groomsmen proposal gift

Groomsmen proposal drinkware doesn't have to be booze-related. Rustic types and coffee drinkers alike will appreciate these insulated camp mugs. They'll nudge the guys to get energized for the wedding festivities.

ODYSEA Store groomsmen mug camping mug, $28 each, Etsy.com 

Personalized Weekender Bags

Personalized gym bag groomsmen proposal gift

These custom duffles will come in clutch for the bachelor party and even for transporting stuff around on the wedding day. Gift them with cards that ask the gents to join you on your "next big adventure."

The Knot Shop weekender bag, $20 each, TheKnotShop.com 

"Will You Be My Groomsman" Bow Ties

Wooden bowtie groomsmen proposal gift

This artist makes quirky wooden bow ties packaged as groomsmen proposals. Choose the design that best suits your crew—like this cowboy boot version for the rowdy Southern or Western crowd. The clips are totally wearable, but also work as keepsakes.

Rustic Love and Wood country bow tie groomsmen gifts, $25 each, Etsy.com

Groomsmen Proposal Cards

Pair a groomsmen proposal card with each guy's gift, or send them out all by themselves. Either option is A-okay! 

Mustache Groomsmen Proposal Cards

Mustache groomsmen proposal card

Tell them you mustache them a question: Will they be your groomsmen? This funny card challenges them to accept the role by sending the groom a pic of them wearing the included faux facial hair.

Nessy's Treasure Shop groomsmen proposal, from $5 each, Etsy.com

"Suit Up" Groomsmen Proposal Cards

Suit Up groomsmen proposal card

These simple cards read, "Bro. This is it. Suit up. Will you be my groomsman?" 

There Forever Studio groomsmen proposal cards, $13 for a set of 10, Amazon.com

Funny Groomsmen Proposal Cards

Funny groomsmen proposal card

It's okay to bribe them just a little—like with an open bar at your reception. Tell them you "know of a great party"—then tell them they're invited and you want to give them a special role.

Mrs. Case's Shop Will You Be My Groomsman or Best Man card, from $4 each, Etsy.com 

Hogwarts-Inspired Groomsmen Proposal Cards

Harry Potter-themed groomsmen proposal card

Shopping for a bunch of Potterheads? These groomsmen proposal cards say, "mischief will be managed—will you be my groomsman?" in a Harry Potter-themed font. 

Mrs. Case's Shop Will You Be My Groomsman or Best Man Harry Potter-style cards, from $4 each, Amazon.com 

Groomsmen Proposal Scratch-Off Tickets

Groomsmen proposal lottery ticket cards

Let them know they've won big getting chosen as one of your attendants. These awesome lottery ticket-inspired cards come personalized with your face, your future groomsman or best man's face, and the "prize" of "will you be my best man?" or "will you be my groomsman?" 

Tanly Designs wedding party Will You Be My scratchers, $4 each, Etsy.com 

To-the-Point Groomsmen Proposal Card

Funny groomsmen proposal card

Wondering how to ask your groomsmen if you're not one for words? This silly proposal card says it all, succinctly: "You're going to be my groomsman. Ok good talk."

Sucky Cards funny groomsmen proposal card, $5 each, Etsy.com

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