How to ask your groomsmen
The groomsman proposal is a newer tradition than the bridesmaid box, and plenty of guys still just ask over a beer. That's completely fine. If you want to make it a little more memorable, follow three rules:
- Fit the guy, not the trend. Your college roommate and your future brother-in-law probably want different things. A shared hobby or running joke is the best starting point.
- Say the words. Even if the gift does the asking, add one or two sentences about why he matters. It's the part people remember.
- Ask everyone within a few days. Group chats move fast. Nobody wants to find out he was asked third.
Groomsmen proposal ideas
From simple to a little more effort. Most of these cost very little and a few are free.
1. Custom bottle labels
- Budgetlow
- Best forbeer or whiskey fans
Print labels for a six-pack of his favorite beer and put a different line on each bottle: "We've had good nights", "We've had bad nights", "We've had nights we don't talk about" and on the last one "Will you be my groomsman?" A bottle of whiskey with a custom label works the same way for one guy.
Tip: Not everyone drinks. For a friend who doesn't, use hot sauce, cold brew or a fancy soda instead.
2. The draft pick card
- Budgetlow
- Best forsports fans
Make a trading card with his photo, "stats" from your friendship and the line "First round pick: groomsman". Hand it over in a card sleeve during a game. For hockey, soccer or cricket fans, adapt the language.
3. A jersey with his name
- Budgetmedium
- Best forteam players
A jersey of your team with "Groomsman" on the back and the wedding year as the number. He'll wear it long after the wedding, probably to the bachelor party first.
4. A pint at your old spot
- Budgetlow
- Best forold friends, UK and Australia
The pub you went to at uni, the bar near your first apartment. Order the drink you always had and ask him there. No props needed, and in the UK and Australia it's about as classic as it gets.
5. Engraved flask
- Budgetmedium
- Best forclassic gentlemen
His initials on one side and the wedding date on the other, with a card that asks the question. Fill it with something he likes before you hand it over.
6. A multitool or pocket knife
- Budgetmedium
- Best forhandy friends
Something he'll carry for years. Engrave "Groomsman" and the year, or keep it plain and put the question on a tag. Check local rules if you plan to travel with it.
7. Socks or a tie for the day
- Budgetlow
- Best forany groomsman
Fun socks with a card: "I can't do this without you knocking my socks off." Or a tie in your wedding colors with the line "I can't tie the knot without you." Cheesy, yes. That's the point.
8. A fishing or golf morning
- Budgetlow to medium
- Best foroutdoor friends
Plan a morning on the water or a round of nine holes. Write the question on a golf ball or hide a card in the tackle box. The quiet time beforehand makes the ask easy.
9. Backyard barbecue
- Budgetlow
- Best fora group of friends
Invite all your groomsmen for a cookout. Before the food comes off the grill, hand each one a beer or a sauce bottle with the question. A good way to ask several guys at once without a formal brunch.
10. Ask during game night
- Budgetfree
- Best forgamers
Name your online lobby or team "Will you be my groomsman?" and wait for him to notice. Or slip the question into a board game card. Works across time zones if you play online together.
11. A mini figure of him
- Budgetlow
- Best forcollectors and builders
Build a little figure in a suit with a tiny sign. Collectible building brick sets make it easy to create a groom and groomsmen lineup that sits on a shelf afterward.
12. A playlist from your years
- Budgetfree
- Best formusic friends
The songs from your road trips, the band you saw together, that one terrible song from senior year. The last track title or the playlist name asks the question.
13. Breakfast at the diner
- Budgetlow
- Best forearly birds
Bacon, coffee, a booth and no pressure. Ask before the food arrives, so you both have something to celebrate with. Easy to do with each groomsman on a different morning.
14. A story on his phone
- Budgetfree
- Best forfriends far away
For the friend who moved across the country: a link that opens into a tiny story with the question, a big Yes button and a short letter. Add a quiz about your friendship ("What did we name the car?") if you like. He answers right there and gets a little ticket with his new role.
Ask the questionTemplate: The big questionBest man proposal ideas
The best man has the biggest job in the groom's party. Ask him first and on his own.
15. An empty ring box
- Budgetlow
- Best foryour best man
Hand him a ring box. He'll panic for a second. Inside: a note that says "You'll be holding the real ones. Will you be my best man?" It points straight to one of his key tasks.
16. A card with his first speech line
- Budgetfree
- Best forfunny friends
Write the first line of his best man speech for him, something like "I've known this guy since he thought cargo shorts were formal wear." Underneath: "The rest is up to you. Will you be my best man?"
17. A real letter
- Budgetfree
- Best forbrothers and lifelong friends
For a brother or someone you've known since childhood, nothing beats a letter. Tell him one memory, what he's meant to you and why you need him next to you. Read it to him or let him read it alone.
18. A weekend away
- Budgetmedium to higher
- Best foradventure friends
Camping, a cabin or a city break. Ask him on the first evening. Good if you want time to also talk about the bachelor party or stag do plans right away.
What to tell them: role and costs
| Topic | Groomsmen | Best man |
|---|---|---|
| Suit or tux | Who pays, rental or buy, when fittings are | Same, sometimes a slightly different look |
| Bachelor party or stag do | Attend, maybe help plan | Usually plans it |
| On the day | Ushering guests, helping with logistics | Holding the rings, keeping the groom on time |
| Speech | Not usually | Often expected, check if he's comfortable |
| Travel | Flights and rooms for a destination wedding | Same |
Planning the party next? See our bachelor party ideas or, for the UK and Australia, stag do ideas.
Will you be my groomsman? Wording to copy
You've been there for every dumb idea I've had. This is my best one yet. Will you be my groomsman?
Requirements: wear a suit, look sharp, don't lose the rings (that's not even your job). Perks: open bar and my eternal gratitude. Will you be my groomsman?
We shared a room, a car and way too many arguments. I want to share this day with you too. Will you be my groomsman?
There's only one guy I trust with the rings, the speech and keeping me calm. Will you be my best man?
You've been my best friend since [year]. It doesn't matter what it's called, I want you up there with me. Will you be my best woman?
Will you be my groomsman? Before you say yes: it's [date] in [place], suits are [rental or buy, who pays] and we're thinking about [bachelor party plan]. Take a day to think about it. Either way, you're stuck with me.
psst … this makes it easier
Ask your groomsmen with a tiny story
A short story on his phone: the big question and a letter from you, with a quiz about your friendship first if you like.
- Add inside jokes and a ridiculous quiz question only he can answer
- He answers with one tap and gets a little ticket with his new role
- Free, no account, no tracking in the invite
More wedding party ideas
Your partner is asking bridesmaids? Our bridesmaid proposal ideas and maid of honor proposal ideas have plenty to steal from. Haven't popped the question yet? Start with our marriage proposal ideas. And when the next big question is "will you be my godfather?", there are godparent proposal ideas too. Everything else is in the occasions guide.
Frequently asked questions
How do you ask someone to be your groomsman?
Pick a moment that suits your friendship, like a beer, a round of golf or a game night, and ask him directly. Add a small gift or card if you like, but the words matter more: tell him why you want him there. Then mention the basics (date, suit, bachelor party) so he knows what he's agreeing to.
What do you put in a groomsman proposal box?
One thing he'll use on the wedding day (socks, a tie or cufflinks), one thing for fun (his favorite beer or snacks) and a card with the question. Three items done well are better than a box stuffed with things he'll never touch.
How do you ask someone to be your best man?
Ask him on his own, before the other groomsmen, and make it clear this is a bigger role. A dinner, a drink at a place that matters to you both or a short letter works well. Tell him what you hope for, like holding the rings and giving a speech, and what's optional.
Who pays for the groomsmen's suits?
It varies. Often groomsmen pay for their own suit or tux rental, while some couples cover it or contribute. Whatever you decide, say it when you ask so nobody gets a surprise bill.
Can a woman be a groomsman or best man?
Yes. A best woman or groomswoman is common and the role works the same way. Ask her what she'd like to wear and what title she likes, and adjust the gift to her.