10 Groomsmen Proposal Ideas They'll Love



One of the best parts of your wedding day is having your closest friends and family stand beside you as you say I do. It’s a deeply personal decision, and no two lineups are decided the same way. You might opt for a bevy of your closest friends, or stick to just family—or a combination of the two. The most important thing to remember is this: A groomsman is an honored position that you want to fill with the best of the best.

But how exactly are you supposed to ask them to join in as more than just a wedding guest? When it comes to how soon is too soon to ask, the sooner the better, and once you have the list confirmed (it’s always good to run it by your other half so everyone’s on the same page), it’s time to start thinking just exactly how to pop the question. Whether you’re down for an all-out guy’s trip or would rather opt for a gift full of personalization, the moment can be memorable and still communicate the significance of their role.

We’ve compiled 10 ways to ask that will definitely have your groomsmen saying "yes!"

01 of 10

Do It With Cufflinks

Send your groomsmen down the aisle in style with the final piece of their look: cufflinks! The ultimate accessory, cufflinks tie an entire look together. Take it one step further by personalizing each set with their monogram or nickname, providing something they can wear over and over again.

02 of 10

Monogram It

Weddings and monograms go hand-in-hand—groomsmen included. Opt for a full 3-letter monogram, or keep it simple with just their first initial on anything from a baseball cap to a tie clip you’d like them to sport on the wedding day. 

03 of 10

Plan a Trip

Whether next-level luxury accommodations, a low-key camping trip, or somewhere in between, we love the idea of rallying with your crew together. Plan an extended stay in a place that holds sentimental value for an extra special punch.

04 of 10

Make It a DIY Project

Assemble an assortment of all of their favorites in a do-it-yourself gift box. Toss in some snack options, a six-pack of their favorite beverage, and maybe even something they’ll need on the wedding day, from cologne to comfortable slippers or shoes. 

05 of 10

Customize It

Socks are the perfect opportunity for groomsmen to show off their personality, so gift them with a pair upon proposal. Go fully personalized with a unique pair for each friend or keep it super easy by having a coordinated look with the same design for each.

06 of 10

Play Up the Accessories

If you’ve planned well-enough ahead, gift each groomsman with the accessories you’d like them to don on the big day: bowties, pocket squares, or even a pair of suspenders are a great way to do the big reveal. Put everything together in one gift box for a foolproof way to pop the question; add in a personal note of please and thanks to really seal the deal.

07 of 10

Incorporate Your Destination

Build your own pack of must-try snacks for a proposal special delivery. Planning a destination wedding? Incorporate snacks from your final destination and put together a meal kit they can cook themselves to get them in the mood—and wish them bon appetit!

08 of 10

Keep It Personal

Choose from a variety of practical gifts like a duffle bag, backpack, or dopp kit. Regardless of the gift, the extra step of personalization will take your appreciation for your friends and desire to have them stand beside you a long way—straight to the aisle, in fact.

09 of 10

Say It With Words

Keep it simple and easy but still meaningful with a handwritten card. There are a variety of options for groomsmen proposal cards, from sentimental to witty and everything in between. Just remember, while the card might say it best, no one can say it better than you can, Give a nod to good times past, present, and future, and finish things off with the question you really need the answer to.

10 of 10

Prepare Them Ahead of Time

Being prepared is one of the rules of tying the knot, and that should absolutely extend to the wedding party! Gift a wedding day prep kit as your proposal that covers every portion of your day: getting ready must-haves like shaving cream and a razor and a pair of sunnies for pictures (or the ceremony if held out of doors).

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