Best Man & Groomsmen Proposal Box Ideas

Looking for ideas for a groomsmen proposal box or a a will-you-be-my-best-man gift? These boxes are thoughtful, heartfelt, and personal.

Need groomsmen gifts & groomsmen proposal ideas? Here is an example of a groomsman proposal box

It’s no secret that I love to make things and will accept almost any opportunity to craft! So I volunteered my DIY services to Lawrence when it came time to propose to his groomsmen. He gladly accepted.

I used a similar concept for these be-my-best-man ideas that I used for the maid of honor box and bridesmaid boxes I made.

But of course I made the asking-groomsmen proposal boxes and will-you-be-my-best-man box more masculine!

I said “yes” to Lawrence’s sweet proposal back in November. He then proposed to his wedding party at our engagement party in March. No matter who you’re asking to take part in your wedding day, you’ll want to make the proposal special. 

Because you may be on a wedding budget, I’m including what I spent on the DIY best man proposal box and each of the groomsmen proposal boxes, plus the links for everything I purchased.

Lawrence proposed to his best man, Tom, at our engagement party in March.
Lawrence proposed to his best man, Tom, at our engagement party in March.

I hope you find these ideas helpful, and I’d love for you to add your own ideas (including any will-you-be-my-best-man ideas!) to this post in the comments section.

What to put in a proposal box

When it comes to groomsmen proposal box ideas, I wanted each gift to be a little different so it would suit the unique interests and personalities of each member of the wedding party.

But the overall look of each box was the same, and here are the supplies I used to create the base for each box:

Gift box with coffee and candy inside

Photo boxes

When it comes to asking groomsmen to be in your wedding, some sort of box is required. I found plain black photo boxes and used watercolor pens to write out all the guys’ names on card stock. I then glued the names onto the boxes.

Proposal stickers

I found super cute designs on Amazon for the groomsmen proposal boxes. The proposal stickers are meant to be stuck onto liquor bottles, but I attached them onto the inside of the boxes. When a groomsman opened the box, he was proposed to!

Tissue paper

I bought a giant bag of tissue paper and used this as the base for each box. Because I wanted to “fill up” space at the bottom of the box, I placed crumpled-up plastic grocery bags underneath the tissue paper.

Ring Pops, Hershey’s Kisses, and Hershey’s Hugs

I had made DIY engagement favors for our engagement party, so each guy got a bag of candy (with a Ring Pop!) with his proposal gift. Find out how we had an engagement party on a budget.

Lawrence with his groomsman, groomswoman, and best man.
Lawrence with his groomsman, groomswoman, and best man.

Unique groomsmen gift ideas

Next up is the part of the will-you-be-my groomsman ideas that are unique to each guy. The great groomsmen will love receivingthe unique groomsmen proposal boxes.


This is a no brainer for a groomsman proposal, right? Lawrence’s best man, Tom, loves Fireball and Jameson, so he got little bottles of each in his be-my-best-man box.

Whatever your guys love, get a bottle of their favorite alcohol. I paired the alcohol with little shot glasses.

No doubt these shot glasses will make it to the bachelor party! FYI that while I picked up the bottles at a local liquor store, you can also buy smaller liquor bottles online.

Martini shaker

I saw this little shaker and thought it would make a cute addition to one of the guy’s boxes!

Beer cooler

Tom loves beer. When I saw this reusable beer cooler, I thought he would love it. And he did. When Tom opened his will-you-be-my-best-man gift, he said, “it’s a box of all my favorite things!”

I thought about also including a cute bottle opener with the groomsman gift, and you totally could, but I know that Tom already has one.

Candy jar

When it came to thinking of asking-groomsmen ideas, I had some alcohol-free visions up my sleeve. Kode doesn’t drink, so Lawrence and I thought of the candy jar idea together.

We filled a glass jar with Werther’s candies. For Frank, we filled a candy jar with caramel creams, as well.

Tea and honey

I wanted every box to contain a celebratory beverage. So for Kode, I added caffeine-free herbal tea and mini honey jars. The honey is from the United Kingdom, where Lawrence and I will be getting married.


Frank prefers coffee to tea, and we wanted his proposal box to match the coffee-themed bridesmaid box that his wife, Sara, got. So I added Starbucks Breakfast Blend ground coffee to his box.

Lawrence proposed to his brother-in-law, Frank, on Christmas.
Lawrence proposed to his brother-in-law, Frank, on Christmas.


What’s coffee without a mug to go with it? I like how the message of this mug literally is “happy” but that it still looks masculine. The Rae Dunn line also makes adorable “Dad” mugs and “good morning” mugs.


Kode enjoys traveling (and we are having a destination wedding), so I thought he would enjoy a travel-inspired journal.

Groomsman proposal box with assorted items inside

Staying on budget

All in all, each proposal box cost an average of $39. That’s not so bad for asking your best man and your closest friends to be a part of your wedding!

Kode doesn\'t drink alcohol, so he got a special box of hand-picked culinary selections.
Kode doesn’t drink alcohol, so he got a special box of hand-picked culinary selections.

More groomsmen gift ideas

If you need even more gift ideas for the big day proposal, here you go!

Our bridal party consists of one best man, two groomsmen, and one female groomsman. I made Tara’s box a cross between a bridesmaid proposal box and a groomsman proposal box. I’ll be sharing the contents of her box soon.

Groomsman proposal box with tea and candies inside

Supplies to make each proposal box

Here are the supplies I bought to make each of the groomsmen proposal boxes, as well as the will-you-be-my-best-man box:

*If you’d like to do all your shopping in one place, here are similar items I found on Amazon:

Groomsman proposal box listicle

Bottom line

You can easily create heartfelt groomsmen proposal boxes for your wedding party. You can craft each box to reflect the personality and preferences of each guy.

More wedding planning help

Proposing to your bridal party? Get suggestions on what to put in a bridesmaid box

For more wedding-related content, check out my website. In particular, I think you’ll enjoy these posts:

Looking for ideas for a will-you-be-my-best-man gift? Or how about groomsman proposal ideas? These ways to ask groomsmen are thoughtful, heartfelt, and personal.

I’d love to hear from you! What ideas do you have for a groomsmen proposal ideas or a will-you-be-my-best-man gift? Have you or your significant other received a heartfelt best-man proposal box? How did you pop the question and add a personal touch or two?

Weddings |

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