17 Fun Groomsmen Proposal Ideas That Feel Totally You

Asking your best friends to stand by your side on your wedding day is one of those once-in-a-lifetime moments that deserves a little thought—and a lot of heart. Whether you’re going for something funny, meaningful, or somewhere in between, there are endless ways to make your groomsmen proposals memorable. Here are 17 thoughtful and fun groomsmen proposal ideas to help you pop the question in a way that feels completely your own.

14 Groomsmen Proposal Ideas

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1. Groomsmen Proposal Gift Box

A custom gift box is a classic for a reason. Fill it with small, meaningful items like mini bottles of tequila, personalized socks, a cigar, or even a note asking, “Will you be my groomsman?” It’s a chance to include a mix of practical items they’ll use for the wedding and playful touches that reflect your friendship. Tailor each box to the individual for a thoughtful surprise they won’t forget.

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2. Film a Confessional-Style Video

Channel your inner documentary star and record a confessional-style video, reality-show style or like “The Office”. Talk about your wedding planning process, why you need your crew, and what role each guy plays in your life. Keep it funny, sincere, or totally offbeat—whatever feels most like you.

3. Use Your Save the Date

Turn your save-the-date into more than just a wedding announcement. When you hand deliver it, write a note on the back or include a slip of paper that reads, “You’re not just invited… you’re my groomsman.” It’s a simple yet charming way to deliver the proposal during a moment that already carries meaning.

4. Write a Letter

A handwritten letter may seem old-fashioned, but that’s what makes it so impactful. Share a few favorite memories, express why their friendship matters, and ask them to stand beside you on your big day. Whether you keep it lighthearted or sentimental, a letter makes the moment feel personal and real.

5. Shot Bottle with a Note

A small shot bottle makes a fun, no-fuss gift, but it’s the note that really brings it home. Whether you go sincere or sarcastic, it’s the perfect place to thank them for being part of your life and ask them to join your wedding day lineup. You can keep it classic with “Take a shot—then take a tux,” or customize it with an inside joke they’ll instantly recognize. Wrap it all up in a box or hand it over in person for a moment that feels personal without being over the top.

6. Plan a Surprise Announcement During an Event

Whether you’re at a tailgate, a weekend getaway, or just a night out with your crew, use the moment to make a surprise announcement. Wait for a break in the action and casually ask your future groomsmen. It feels spontaneous, memorable, and totally in the moment—plus you get to see their reactions firsthand.

Read More: 38 Creative And Unique Bridesmaid Proposal Gift Ideas

7. Ask During Game Night

Next time you host a poker night or video game session, work your proposal into the evening. Maybe the winner gets a surprise envelope, or you write it on a card and reveal it during the game. It’s low-pressure, laid-back, and fits seamlessly into your usual hangout vibe.

8. Record a Movie Trailer

If you want to go big, record a fake movie trailer starring—you guessed it—your wedding crew. Use dramatic music, fake action scenes, and over-the-top narration that ends with your ask. Something like: “Coming soon… to a wedding near you… [Friend’s Name] as the Best Man.” Funny and unforgettable.

9. Fake Summons Letter

Surprise your groomsmen with a letter that looks suspiciously like legal trouble—until they read the fine print. A fake summons letter, complete with official language and dramatic tone, sets the stage for a laugh-out-loud reveal: they’ve been “officially requested” to serve as your groomsman. It’s unexpected, clever, and perfect for a group that doesn’t take themselves too seriously. Bonus points if you print and seal it in a formal envelope for full effect.

10. Include It in a Toast

If you’re already together for dinner or drinks, wait until everyone has a glass in hand and give a quick toast. Mention how important these guys are to you, thank them for being part of your life, and then ask if they’ll stand with you on your wedding day. It’s casual but heartfelt, and it turns a normal night into something special.

11. Bottle Cap Message

Add a secret twist to a round of beers by customizing the underside of a bottle cap to reveal the message: “Be my groomsman?” You can order personalized caps or make your own. Hand them their drink, let them pop it open, and enjoy the moment when they discover what’s underneath.

12. Scratch-Off Card Surprise

A scratch-off card adds a fun, interactive twist to your proposal. You can order them online or create custom ones with your own message hidden beneath the surface. It’s quick, playful, and works perfectly for mailing or handing off during a casual hangout.

13. Fake Video Game Covers

For the gamer crew, a fake video game cover turns your wedding into the ultimate co-op quest. Design a personalized game case like “Call To Duty”. This strikes the perfect tone between goofy and nostalgic. Pair it with a little controller keychain or a snack from your gaming nights to complete the gift.

14. Tickets to a Shared Experience

Instead of a gift, give the promise of time together. Buy tickets to a game, concert, or comedy show you both love, and ask them to be your groomsman before or during the event. The shared experience becomes part of the proposal, which makes it that much more memorable.

15. Funny Proposal Cards

Sometimes a good laugh says it best. Give your guys a funny card with a joke, pun, or inside reference. It’s a simple gesture, but if the humor hits home, it’ll feel just right.

16. Nice Dinner with a Twist

Invite your friends to a laid-back dinner—nothing fancy, just good food and good company. At some point between courses (or maybe over dessert), thank them for being part of your life and pop the question. It’s an easygoing but thoughtful setting that feels authentic and real.

17. During a Golf Outing

If you and your friends love to golf, turn your next round into a subtle proposal moment. You can ask during the back nine, make a joke about “teeing up” your wedding party, or surprise them at the clubhouse. It’s a great way to blend the ask into something you already enjoy together.

Concluding Thoughts: Your groomsmen proposal doesn’t need to be over-the-top to be unforgettable. Whether it’s through humor, heartfelt words, or a shared moment, what matters most is that your ask feels like you. These ideas offer a mix of thoughtful gestures and fun moments to help you create a proposal that reflects your personality—and your bond with the guys who’ll stand beside you.