How to Ask Groomsmen to Be in Wedding (25 Ideas)

Inviting your closest friends to be part of your wedding as groomsmen is a special moment, and finding a memorable way to ask them adds to the excitement.

Whether you’re looking for something meaningful, fun, or a little over-the-top, there are countless creative groomsmen proposal ideas to make the occasion unforgettable.

Here are 15 unique ways to ask your groomsmen to stand by your side on your big day.

1. Personalized Gift Boxes

Create a custom gift box filled with items your friend loves, such as small bottles of alcohol, snacks, or grooming products. Including a handwritten note about why you want them as a groomsman makes the gesture even more heartfelt, showing them just how much they mean to you. This gift box is a great keepsake and adds a touch of class to your proposal.

2. Groomsmen Proposal Cards

Sometimes, a well-thought-out card is all you need. Write a funny or touching message inside a “Will You Be My Groomsman?” card to set the right tone for your proposal. You can go for a humorous message if your friendship is more playful or a heartfelt note to express your appreciation. Pair the card with a small keepsake, like a tie clip or cufflinks, to make the gesture feel extra special.

3. Customized Whiskey or Beer Glasses

Give your friend a personalized glass engraved with their name and "Groomsman." Pair it with their favorite drink for a classy, memorable ask that they can keep long after the wedding. Not only is this a practical gift, but it’s also a thoughtful way to toast to your friendship and the special memories to come.

4. Miniature Bottles of Favorite Spirits with Tags

Attach a small “Will You Be My Groomsman?” tag to miniature bottles of their favorite spirit. This is an affordable, fun, and easily personalized gift, especially if you select a spirit that has meaning for your friendship or reflects their personality. This is a simple yet memorable way to ask them to stand by your side.

5. A Box of Cigars

For a classic touch, gift your friend a cigar box with a personalized lighter or cutter and a note asking them to be your groomsman. It’s a thoughtful gift they can enjoy and share with you on the big day, creating a memorable moment and marking the occasion in style. Add a card with a personal message to make it extra special.

6. Event or Activity Invite

Invite your friend to a fun activity like a round of golf, a sports game, or a brewery tour, and make your groomsman proposal part of the experience. This approach makes the ask more about shared memories and quality time, and it’s perfect for friends who love activities. Use a personalized gift, card, or drink label to pop the question to your groomsman during the event.

7. Custom Clothing or Accessories

Gift your friend an item like cufflinks, a tie, or socks with a personalized message. It’s a practical gift they can add to their wedding attire, adding sentimental value and ensuring they’ll be reminded of the special role they play in your life. Personalizing the classy gift with their initials or “Groomsman” makes it even more meaningful.

8. Engraved Multi-Tool or Pocket Knife

For an outdoorsy or handy friend, give a personalized multi-tool or pocket knife. Engrave it with their name or “Groomsman,” creating a useful keepsake they can cherish long after the wedding ceremony. This is an especially thoughtful choice for friends who value practicality and outdoor activities.

9. Photo Memory Book

Compile a small album of favorite photos together, with captions or stories that capture your friendship. On the final page, add a message asking them to stand by your side. This heartfelt approach is ideal for future groomsmen, close friends, or family members, as it shows the journey of your relationship and makes them feel appreciated.

10. Customized Bobblehead or Action Figure

For a humorous, unique touch, create a custom bobblehead or action figure of your friend. Attach a speech bubble with “Will You Be My Groomsman?” for a fun keepsake they’ll treasure. This groomsmen proposal gift is perfect for friends with a good sense of humor, and it’s sure to make them smile every time they see it.

11. Retro Video Game Proposal

If you share a love for video games, gift a classic cartridge with a custom label reading, “Will You Be My Player 2?” It’s nostalgic, playful, and personal, especially if you and your friend spent hours gaming together. You could even invite them over for a gaming night to make the proposal even more memorable.

12. Groomsman Survival Kit

Assemble a “survival kit” as part of personalized groomsmen gift boxes with essentials like mints, Advil, a small bottle of spirits, and a tie. Label each item with a funny note, and package it as a “Groomsman Survival Kit” for a lighthearted touch that can break the ice. These gift boxes add a sense of humor to your proposal while also providing practical items all your groomsmen might need on the big day, making them both fun and useful keepsakes.

13. Customized Mini Jersey or Sports Memorabilia

For a sports fan, give them a mini jersey or sports cap with their name, “Groomsman,” and even a hint about the upcoming bachelor party on it. This thoughtful gesture shows you know what matters to them, and it’s something they can proudly display or wear. If your friend is a major sports enthusiast, they’ll love this personalized approach to asking them to be in your wedding while looking forward to the bachelor party festivities.

14. An Adventure or Road Trip Invitation

Plan a special outing or adventure like a hike or camping trip, and ask them during a scenic or meaningful moment. This way, the setting adds an extra layer to the memory, making it a special and unforgettable experience. This idea is perfect for friends who enjoy the outdoors and value meaningful shared experiences.

15. A Lighthearted “Contract”

Draft a playful “Groomsman Contract” that humorously outlines their responsibilities, such as keeping you calm, ensuring the rings are safe, and being ready to hit the dance floor. It’s a funny, creative way to show them you value their role in your big day. Add a signature line and have them sign, creating a keepsake they’ll laugh about for years.

16. Groomsman Scratch-Off Cards

Add an element of mystery to your proposal with personalized scratch-off cards. Under the scratch-off area, reveal a message like “Will You Be My Groomsman?” or something tailored to your friendship, making the moment feel even more special. It’s a creative way to pop the question, and the card becomes a sentimental keepsake they can cherish, reminding them of the unique way you asked them to be part of your big day.

17. Customized Pop-Open Champagne or Beer Bottle

Send a bottle of champagne or beer with a custom label saying something playful like “Pop me open to find out!” or “Cheers to being my groomsman.” Inside the cap or attached to the bottle, include an invitation with the official question, adding an element of surprise. This interactive approach not only delivers your message in a celebratory way but also gives them a reason to toast with you in spirit, kicking off the wedding festivities early.

18. Map to the Wedding Day

For friends who love travel and adventure, a custom map with your destination wedding location and key spots tied to your friendship is a thoughtful touch. Mark the location for “Best Man” or “Groomsman” and include a note that explains this is where they’ll stand on your big day, adding a layer of sentimentality. This personalized map turns a simple question into a journey through your shared memories, making it a meaningful keepsake they’ll treasure.

19. Personalized Sports Gear

For your sports-loving best friends, personalized baseballs, custom golf balls, or footballs engraved with “Will You Be My Groomsman?” or their name is a perfect choice. You can even play a game with them and ask mid-throw for an unforgettable moment. This unique keepsake not only reflects their interests but also adds a playful, memorable twist to your proposal.

20. QR Code Surprise

Bring some tech-savvy flair to your proposal by creating a QR code that leads to a custom formal invitation video message, website, or online photo album. You can film a heartfelt message, share funny moments, or just ask them to be part of your wedding, making it a personal and interactive experience. This creative approach blends sentiment with technology, making it a standout invitation that they can revisit anytime for a quick smile.

21. Personalized Puzzle

Create a customized puzzle with a picture of you and your friend or a fun design that spells out “Will You Be My Groomsman?” as they complete it. This interactive approach adds a sense of mystery and enjoyment, allowing them to put the pieces together to reveal your special request. It’s a lighthearted yet memorable gesture they’ll appreciate.

22. Groomsman Sock Surprise

Gift your friend a pair of custom socks with a note saying, “In case you get cold feet!” or “Stand with me, one step at a time.” These can be worn at a wedding party, making it both practical and sentimental. Plus, it’s a small gift that adds a humorous touch to your proposal while giving them something to hold onto for years.

23. Movie or Pop Culture-Inspired Proposal

If you and your friend share a love for a specific movie or TV show, incorporate a quote or scene from it into your proposal. For example, a Star Wars fan could say, “Will you be the Chewbacca to my Han Solo?” Adding a bit of pop culture makes the invitation personal and taps into shared interests, making it extra special.

24. Personalized Keychain with Engraving

Gift a simple but meaningful item like a keychain engraved with “Groomsman” or “Best Man,” along with their initials or a meaningful date. Every time they use their keys, they’ll be reminded of your friendship and the role they’ll play in your big day. This small, practical gift combines sentiment and function.

25. A Classic Watch with an Engraving

If you’re looking to give a more timeless gift, a classic watch engraved with a message like “Time to be my Groomsman?” can make a lasting impression. It’s a meaningful gesture that they can wear on the wedding day and keep for years, commemorating the special bond you share.