Congratulations on taking the first steps on your journey down the aisle! With the love of your life by your side and a date set, you’re ready to assemble your crew: your groomsmen. These men will stand by your side as you tie the knot, celebrating the joyful occasion and creating memories to last a lifetime. Asking them should be just as memorable as the day itself, but how can you do that without breaking the bank? Here are some fun, creative, and affordable DIY groomsmen proposals ideas.

1. Customized Labels

A popular, cost-effective way to ask your friends to be groomsmen is by using personalized beer or wine bottle labels. These can be printed at home or ordered online at a low cost. Write a heartfelt message, a humorous quote, or a simple “Will you be my groomsman?” on the label. To complete the package, add their favorite bottle of brew or vino, and you’ve got yourself a charming and personalized proposal.

2. DIY Cigar Boxes

If your friends enjoy a good cigar, why not incorporate that into your proposal? A DIY cigar box is an elegant, masculine option that won’t break the bank. Purchase plain wooden boxes and craft supplies from your local dollar store or online. Decorate each box with the recipient’s initials, filling them with a quality cigar and a small note asking them to stand by your side. This stylish yet straightforward proposal is a classy way to pop the question.

3. Sports Themed Proposals

If your crew is into sports, channel that passion into your proposal. For baseball fans, consider writing your question on a new baseball: “Will you be on my wedding team?” For football enthusiasts, a mini football with a similar message works great. You can even include a jersey or a hat from their favorite team to make it more special.

4. Handwritten Letters

In this age of digital communication, a handwritten letter can be a meaningful and touching surprise. Invest some time in writing a personalized note to each of your prospective groomsmen. Share memories, express gratitude for their friendship, and articulate why you want them to be part of your big day. To add a bit of flair, use sealing wax to close the envelope, giving your proposal a vintage charm.

5. DIY Survival Kits

Another creative idea is to assemble DIY “Wedding Day Survival Kits.” Fill a box or bag with items that could come in handy on the day of the wedding: mini bottles of alcohol, breath mints, a tie clip, or even headache medicine for the morning after. Include a funny note that reads something like, “In preparation for surviving my wedding, will you be my groomsman?” It’s a thoughtful, practical, and fun way to propose.

6. Customized Puzzles

For the puzzle lovers in your life, consider a customized jigsaw puzzle. These can be designed and ordered online without a hefty price tag. Have a photo of you and your friend printed on the puzzle with the words, “Will you be my groomsman?” hidden within the image. As they complete the puzzle, they’ll uncover your proposal, making for a fun and unique surprise.

7. DIY BBQ Sauce or Hot Sauce

If your groomsmen are foodies or love to grill, a DIY BBQ sauce or hot sauce could be a hit. There are plenty of recipes online that can guide you in making these sauces at home. Pour your homemade concoction into a bottle, create a personalized label, and voila! You have a delicious and original proposal.

8. Personalized Socks

A pair of personalized socks can be an amusing and practical groomsmen proposal. With a plethora of online retailers selling custom socks, you can easily find a pair that suits each friend’s personality. Add a witty message like, “In case you get cold feet” or “So you don’t get cold feet, will you be my groomsman?”

9. DIY Video Game Proposal

If your friends are gamers, incorporate that into your proposal. Create a custom level on a game like Minecraft or Fortnite that leads to a sign asking, “Will you be my groomsman?” This creative and personalized proposal will certainly be memorable for your gaming buddies.

10. Custom Engraved Tools

For the handyman in your life, consider a custom-engraved tool as a groomsmen proposal. Engrave a small message or your friend’s initials onto a practical tool, like a pocket knife or multi-tool. Every time they use it, they’ll be reminded of your special day.

11. DIY Coffee Lover’s Package

If your prospective groomsmen are coffee aficionados, assemble a coffee lover’s package. Include a bag of their favorite gourmet coffee, a personalized mug, and a note asking them to be your groomsman. This simple and thoughtful proposal is sure to warm their hearts.

12. DIY Movie Night Kit

Assemble a movie night kit with their favorite snacks, a DVD or Blu-Ray of a film you both love, and a note proposing your question. It’s a fun, inexpensive proposal idea that your friends are sure to appreciate.


Remember, the best groomsmen proposals are those that truly reflect the unique bond you share with each of your friends. It’s not about how much money you spend, but the thought, creativity, and love you put into each proposal. No matter which DIY idea you choose, what matters most is the genuine sentiment behind it, making your friends feel special and appreciated.

Your wedding day is one of the most important days of your life, and having your closest friends by your side makes it all the more special. By crafting unique and personal groomsmen proposals, you’re not just asking your friends to stand with you; you’re creating memories that both you and your groomsmen will cherish for a lifetime. Happy planning!

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Our boxes can be personalized to match each of your friends’ unique personalities and tastes. Whether they’re a sports fan, a wine connoisseur, a gamer, or a coffee lover, we have the perfect box to wow them.

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So why wait? Make your groomsmen proposal an unforgettable experience with our high-quality, customizable groomsmen proposal gift boxes. Click here to browse our collection and place your order today. Don’t just ask your friends to stand with you on your big day – make it a memory to cherish forever with our unique groomsmen proposal gift boxes. Your friends deserve nothing but the best, and we’re here to help you deliver just that.