15 Ideas to Ask Groomsmen to Be in Your Wedding Creatively

15 Ideas to Ask Groomsmen to Be in Your Wedding Creatively

ByBells Of Joy Team Reading Time: 5 minutes

Choosing your groomsmen is a big part of planning your wedding. These are the friends or family who’ll stand by your side, so asking them in a memorable way really matters.

A groom giving personalized boxes to his friends outdoors as he asks them to be his groomsmen.

Finding creative ways to ask your groomsmen shows you truly value their support. Whether you want something simple or a bit more out there, the important thing is making it personal.

1) Send a formal groomsmen invitation card

A formal groomsmen invitation card on a wooden table surrounded by a bow tie, cufflink, boutonniere, and fountain pen.

Send a formal card to invite your friends to be your groomsmen. It shows you’ve put some thought into it.

A nice card makes things feel special. Toss in the date and a few details about your wedding day.

Check out formal invitation examples online if you’re stuck for ideas.

2) Gift a personalized flask with their initials

A personalized metal flask with engraved initials on a wooden table surrounded by a bow tie, cufflink, and handkerchief.

A personalized flask is a classic way to ask your groomsmen. Go for stainless steel, leather, or cork—whatever suits your crew.

Engrave their initials to make it unique. It’s practical and doubles as a keepsake.

Add a small note for a personal touch. You can browse engraved flasks with initials for more inspiration.

3) Ask them with a custom engraved pocket watch

Close-up of an open engraved pocket watch on a wooden table surrounded by a suit jacket sleeve, boutonniere, and a partially visible note.

Give your groomsmen a custom engraved pocket watch. It’s a special gift they can keep long after the wedding.

Add a meaningful message or their initials. It’s both stylish and practical.

If you want more ideas, check out unique pocket watch gifts.

4) Present a ‘Will You Be My Groomsman?’ whiskey bottle

A whiskey bottle on a wooden surface surrounded by a wristwatch, cufflinks, and a notebook in a warm, cozy setting.

Hand your groomsmen a special whiskey bottle with a custom label that pops the question. It’s a simple, thoughtful move.

Pair it with a note or card for a nice touch. Sometimes, the little things make the biggest impact.

For more personalized whiskey gifts, check out this collection.

5) Organize a surprise game night proposal

A man smiling and holding a ring box while surrounded by friends playing board games in a cozy living room.

Invite your friends for a game night. Keep it relaxed and fun.

When the time feels right, pause the games and ask them. You can even hand out small gifts or notes with your proposal.

6) Slip a note inside their favorite book

An open book on a wooden table with a folded note slipped inside, surrounded by a boutonniere, ribbon, and a fountain pen.

Surprise your groomsmen by hiding a little note inside a book they love. When they find it, they’ll get your message.

It’s personal and proves you know what they enjoy.

7) Create a custom puzzle revealing the question

Close-up of hands assembling a custom jigsaw puzzle on a wooden table with wedding-themed icons and stationery nearby.

Give them a puzzle to solve. Each piece reveals part of your question.

It’s fun and interactive—and who doesn’t love a puzzle? You can find creative options online.

8) Send a funny personalized meme via text

Four men laughing and looking at a smartphone together in a cozy living room with wedding decorations.

Send a funny meme that fits your inside jokes. Add their name or a quick message asking them to join your wedding.

It’s a lighthearted way to ask and takes almost no time at all.

9) Gift a grooming kit with a handwritten card

A grooming kit with shaving tools and a handwritten card placed on a wooden surface, with wedding-related decorations nearby.

Hand your groomsmen a grooming kit with essentials like a razor, comb, and lotion. It’s something they’ll actually use.

Add a handwritten card to ask them to be part of your day. That personal note really matters.

10) Invite them to a BBQ and pop the question

A group of men outdoors around a barbecue grill, smiling and talking as one man holds a small gift box.

Host a relaxed BBQ. Everyone loves good food and good company.

While you’re hanging out, ask them to be your groomsmen. No pressure, just a genuine moment.

11) Use a custom bobblehead of the groom as a gift

A custom groom bobblehead on a wooden table surrounded by wedding invitations and gift boxes.

Give your groomsmen a custom bobblehead of yourself. It’s quirky and personal.

They’ll probably laugh—and remember your wedding every time they see it. You can customize these to match your style.

12) Give a custom leather keychain with the date

A custom leather keychain on a wooden surface surrounded by wedding-related items.

Hand out custom leather keychains with your wedding date. They’re practical and look good.

Every time your friends grab their keys, they’ll think of your big day. It’s thoughtful without being over the top.

13) Record a heartfelt video message

A groom sitting in a living room recording a heartfelt video message on his phone.

Record a sincere video message. Just speak from the heart and say why you want them with you.

A video’s perfect if you can’t ask in person. It feels honest and real.

14) Send a craft beer set with a personal tag

A craft beer gift set with personalized tags arranged in a wooden box alongside wedding accessories like a boutonniere and bottle opener.

Send your groomsmen a craft beer set. Add a tag with their name and a quick message.

It’s a simple gesture, but it goes a long way. Plus, who says no to beer?

Personalized beer tags make your invite stand out. You can find ideas for custom groomsmen beer labels.

15) Ask with a pair of matching cufflinks

Close-up of matching silver cufflinks resting on a wooden surface next to a folded white dress shirt with French cuffs.

You can ask your groomsmen by handing them a pair of matching cufflinks. It’s a classic move that says you want everyone to look sharp and coordinated on the big day.

Matching cufflinks make a simple but thoughtful gift. Plus, they can pull them out for other formal events later—so they’re practical, not just a one-time thing.

Pick cufflinks that work with your wedding’s style or colors to make the gesture feel more personal. If you need ideas, check out some wedding cufflinks for inspiration.

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