Best Man Invitation: Groomsman Proposal Cards

So You Need Groomsman Proposal Cards

Okay so groomsman proposal cards are basically a thing now and honestly they’re kinda fun but also you can totally overthink them which I see happen ALL the time. The concept is simple – instead of just texting your buddy “hey wanna be my groomsman” you give them an actual card or box that asks the question in a more formal way. It’s like the wedding industry version of a promposal but for grown men.

I had this groom back in spring 2023 who spent THREE WEEKS agonizing over these cards and I’m like dude your wedding is in eight months we have actual problems to solve here but whatever makes you happy I guess. He ended up going with custom leather keychains inside each card which was actually pretty nice but the point is you don’t need to make this your entire personality.

When to Give Them Out

Timing matters more than you’d think. You wanna do this like 8-12 months before the wedding ideally. Earlier is fine too if you’re one of those super organized people (I’m not judging but also I am a little bit). The reason is your groomsmen need time to budget for their tux rental or purchase, bachelor party, travel if it’s a destination wedding, and all that stuff.

Don’t do it too early though because I’ve seen friendships change or people move across the country and then it gets awkward. Like you asked someone 18 months out and now you barely talk to them but they already posted about it on Instagram so now what.

Also consider if you’re gonna do them all at once or separately. Most grooms do them around the same time which makes sense logistically but some guys like to make it individual moments. Your call really.

What Actually Goes On The Card

The wording doesn’t need to be shakespeare or whatever. Keep it straightforward. Something like “Will you be my best man?” or “I can’t say I do without you” or “Groomsman?” with a question mark. That’s literally it.

Some cards get super sentimental and that’s fine if that’s your vibe but honestly most guys I work with keep it simple. You can add a personal note inside if you want – like a specific memory or inside joke – but the front should be clear about what you’re asking.

What drives me absolutely nuts is when people make the card SO decorative and fancy that you can’t even tell what it’s asking. I’ve seen cards that are all geometric patterns and gold foil and nowhere does it actually say “will you be my groomsman” until you open it and read three paragraphs. Just… make it clear from the start.

Design Options That Actually Work

You’ve got options here and it depends on your budget and how crafty you’re feeling:

• Printed cards from Etsy or Minted – This is the easiest route. You can find templates for like $3-15 per card depending on how fancy you go. They usually come as digital downloads you print yourself or you can pay extra for printing.
• Custom designed cards – If you want something that matches your wedding stationery exactly I can help with that (shameless plug sorry) or any stationer can design something custom. Costs more obviously.
• DIY cards – Hit up Michaels or Hobby Lobby, get some cardstock, print your own. Takes time but saves money.
• Boxed proposals – These come with the card plus some gifts inside. More on that in a sec.

The style should kinda match your wedding vibe if possible but honestly nobody’s gonna be like “wow this card doesn’t match the wedding aesthetic” so don’t stress too much. Rustic weddings usually go with kraft paper and twine, formal weddings might do letterpress or foil, beach weddings might have nautical themes. You get the idea.

The Whole Box Situation

So somewhere along the way these proposals evolved from just cards to entire gift boxes and now that’s like the expected thing which is… a lot. But if you wanna do it here’s what people typically include:

• The actual proposal card
• A small bottle of liquor (mini whiskey bottles are super popular)
• Socks with funny sayings
• Sunglasses for the wedding day
• A flask or bottle opener
• Cigars
• Gift cards to places like Amazon or Starbucks
• Personalized items like cufflinks or tie clips

My cat knocked over an entire box of these mini whiskey bottles I was organizing for a client once and it was a whole disaster but that’s beside the point.

You don’t need to include gifts though. Seriously. The card itself is enough. The gifts are nice but they also add like $30-50 per person to your cost and you’re already spending a fortune on this wedding so maybe save your money for the open bar.

Budget Breakdown

Let’s talk actual numbers because I think people don’t realize how this adds up:

Budget option: $5-10 per person. This is a printed card from Etsy that you print at home or at FedEx, maybe in a nice envelope with a handwritten note inside.

Mid-range option: $20-40 per person. Professionally printed card, maybe in a small box with one thoughtful gift like a personalized beer glass or a nice bottle opener.

Fancy option: $50-100+ per person. Custom designed card, wooden box, multiple gifts, personalized everything, the works.

Multiply that by however many groomsmen you have and yeah it adds up quick. I had a groom spend $600 on these proposals and then complain about the cost of reception napkins which was… a choice.

Personalization Ideas

If you wanna make each card unique to each guy that’s actually pretty cool. You could reference:

• How you met
• A specific memory together
• An inside joke
• Their role in your friendship
• Why you specifically want them standing next to you

For your best man the card should probably be a little different than the groomsmen cards. Maybe it says “best man” specifically or has a different design or comes with a slightly nicer gift. He’s got more responsibilities than the other guys so acknowledging that is good.

Some grooms do different colored cards for each person or different quotes or whatever. That’s gonna take more effort and planning but if you’re into that sorta thing go for it.

Presentation Matters Kinda

How you actually give these out is up to you. Some ideas:

• Mail them if people live far away
• Hand deliver them individually
• Give them out at a group hangout
• Leave them on their doorstep with a knock
• Include them in a bachelor party invitation

I personally think individual moments are nicer because it feels more personal but I also know that’s not always realistic if you’ve got like 8 groomsmen and they’re scattered across different states. Do what makes sense for your situation.

If you’re doing it in person you don’t need to make a huge production out of it unless that’s your thing. Just be like “hey man I wanted to ask you something” and hand them the card. They’ll figure it out.

What If Someone Says No

This is awkward but it happens. Maybe they can’t afford it, maybe they’re dealing with personal stuff, maybe they just don’t wanna be in a wedding. It’s gonna sting but try not to take it personally.

This is why you don’t post about your groomsmen on social media until everyone has accepted. I’ve seen situations where a groom announces his whole wedding party and then someone backs out and it’s messy.

Have a backup person in mind just in case but don’t like, tell them they’re a backup obviously. That’s not a great feeling for anyone.

DIY Instructions If You’re Going That Route

Alright so if you wanna make these yourself here’s basically what you do:

Get cardstock from any craft store – 5×7 is a standard size that’s easy to work with. You can buy pre-scored cards that fold or just use flat cardstock.

Design your card in Canva or Word or whatever. Keep it simple – your name, their name maybe, the question, the wedding date if you want. Print it at home or take the file to FedEx/Staples for nicer printing.

If you want a box, small kraft boxes or wooden boxes are on Amazon for cheap. Line them with tissue paper or crinkle paper.

Add whatever gifts you want, tuck the card on top or attach it to the inside of the lid.

Seal it up with a sticker or twine or just hand it over as is.

The whole process takes maybe 2-3 hours if you’re doing like 6 of them. More if you’re doing fancy calligraphy or something but who has time for that.

Things That Don’t Matter As Much As You Think

Perfect matching – your boxes don’t all need to be identical down to the millimeter

Expensive gifts – a $5 bottle opener is just as meaningful as a $50 flask

Professional photos – you don’t need to hire a photographer to capture the moment unless you really want to

Fancy calligraphy – your regular handwriting is fine

Matching your wedding colors exactly – close enough is good enough

Real Talk About The Whole Trend

Look, these cards are fun and they make a nice keepsake but they’re also kinda gotten out of hand. I see grooms stressing about them when they should be worried about actually planning their wedding or I dunno, their marriage.

The card doesn’t make someone more or less likely to be a good groomsman. Your friendship does that. The card is just a nice gesture.

Also like, we didn’t have these ten years ago and weddings still happened and groomsmen still showed up. So if you don’t wanna do them that’s totally fine too. A phone call or a conversation over beers is just as valid as a fancy box.

Where To Buy Ready-Made Options

If you’re not into DIY here’s where to look:

• Etsy has thousands of options, both digital downloads and physical cards
• Minted and Shutterfly have proposal card sections
• Amazon has pre-made boxes with cards included
• Paper Source if you want something in person
• Local stationers (like me) can design custom ones

Read reviews before you buy because quality varies a lot. Some Etsy sellers are amazing and some send you pixelated junk so just check before you commit.

Timing With Other Wedding Stuff

You should probably ask your groomsmen before you book tux rentals obviously. But you don’t need to wait until every single wedding detail is planned. Like you don’t need your venue booked or your flowers chosen or whatever to ask your buddies to stand with you.

Some grooms wait until after they’re engaged for a few months so the initial chaos dies down. Others do it right away. There’s no wrong answer here.

Just make sure you have your wedding date locked in before you ask because people need to know if they can actually commit to that date. Asking someone to be your groomsman and then changing your wedding date three times is gonna annoy people.

The Best Man Card Specifically

Your best man proposal should be a little different. Not necessarily more expensive but different. Maybe it says “best man” instead of “groomsman” which seems obvious but you’d be surprised. Or maybe it has a different quote or comes with a personal letter explaining why you chose him.

The best man has actual responsibilities – planning the bachelor party, giving a speech, holding the rings, wrangling the other groomsmen. So acknowledging that role specifically is good.

Some grooms give their best man a nicer gift with the proposal. Like if the groomsmen get beer glasses the best man gets a decanter set or something. Not required but it’s a nice touch.

What To Do After They Say Yes

Once everyone accepts, group text time. Get everybody connected so they can start planning the bachelor party and coordinating tuxes and all that.

Send them information about what you need from them – measurements for tuxes, availability for fittings, ideas for bachelor party, whatever. Don’t assume they know what being a groomsman entails because lots of guys have never done it before.

Also be clear about costs upfront. Let them know they’ll need to pay for their tux rental, travel, lodging if applicable, bachelor party costs. Nobody likes financial surprises.

Keep the cards if they give them back to you because they make nice wedding keepsakes. Or don’t, whatever. I’m not your mom.