5 Groomsmen Proposal Ideas They’ll Love

She said “Yes!” and now you’ll both say “I do!”, but before any of that can happen, you need to make the most important decision you’ll have to make. You must decide on and ask your most trusted friends to take this journey with you, right up to the altar— to stand by your side.



This won’t be an easy decision nor should it be. This is an important milestone and to really make this as memorable as it rightfully should be—we’ve got ideas to help you create a one-of-a-kind proposal.



How do you propose and make it unique, memorable—all the things? Without further ado, let’s jump right into 5 unforgettable groomsmen proposal ideas.



1. Sports Fan


bowling bowls on rack


Whether it’s football, soccer, basketball, or bowling—you can make this a groomsman proposal for the ages! Choose which sport you want to go with and get a ball. Then write the big question on the ball in permanent marker—the big question being “Will you be my groomsman?”.



Text or call your friend and ask them to meet you outside. Ideally you will have someone else filming on their phone while you drive up. Toss them the ball (carefully) and watch their face as their expressions go from curious to ecstatic!



A twist on this idea would be to invite them to a basketball court, football field, or bowling alley. Kick back, relax, and when the time is right, break out the ball (which you’d already have stashed at the location) and get ready for some high fives!



2. Outdoor Enthusiast


two men fishing off the shore 


For that outdoor loving friend, a Personalized Compass Rose Gift Box can be engraved with any coordinates, from a favorite fishing hole to camping spot. If you’re looking for incredible groomsmen gift ideas, these beautifully-made custom gift boxes are sublime.



Present the gift box while asking them to be your groomsman. This is a unique, meaningful way to propose to that friend that’s been by your side and will continue to be by your side as you cross this momentous milestone.



3. Beer Lover


man pouring beer out of draught tap


For the friend that’s the life of the party, or the go-to beer connoisseur in the group. A Personalized Beer Growler and Pint Glass Set along with a heartfelt message of appreciation for years of friendship and loyalty will go a long way when asking them to serve as your groomsman. You can see why this is a crowd favorite for groomsmen proposal ideas. 



4. Trend-setter


engraved money clip on whiskey barrell


We all have that friend that dresses to impress and makes a concerted effort to look their best, even if they’re just hanging out at home watching football. Propose a toast to friendship and present them with a Personalized Leather Money Clips or a stunning Personalized Watch Set.



Watch their jaw-dropping reaction as they open the gift and look inside. Put a handwritten notecard on the bottom of the groomsmen gift box so that when they lift the money clip or watch out of the box they’ll see the note asking them to be a groomsman.



5. Comic Relief 

reel viewer


This is a groomsman proposal for the friend that provides comic relief and intuitively knows how to get people to relax and have fun, maybe they’re often told they’re a kid at heart. This is the perfect proposal.



Do you remember View-Master? You look into the red goggle-shaped device and click thru the pictures? It would almost look 3D.



Create Your Own Reel Viewer using your favorite photos and memories of your funny friend. Then, work in a question on the slides: “Will You Be My Groomsman?”. When he opens the gift, he’ll without a doubt be surprised. You’ll get a quizzical look and laugh.



Encourage him to put in the disc and click through the images. As he clicks through the images, you’ll see your friend’s amusement turn to amazement and joy!



Stuck on what to engrave?



You’ve chosen your groomsmen, you’ve got ideas for groomsmen gifts and groomsmen boxes, you’ve decided how you want to propose. But now you’re stuck on what to engrave on the items you want personalized. For ideas and inspiration click here. Looking for even more ideas for one-of-a-kind, unique groomsmen gifts? For recommendations, click here.



Can’t decide between these groomsmen proposal ideas?


We get it. When it comes to finding the perfect wedding gifts, Grain+Oak knows a thing or two about how to make quality unique gifts feel special. Between our personalized groomsmen boxes, genuine wood watches, and unique accessories - there are a lot of great products to choose from. 



For more great gifts and ideas be sure to follow us at @grainandoak to stay up to date on our newest product launches and giveaways!




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Still, have questions? Email our team and we will respond within 24 hours.


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