17 Great Groomsmen Proposal Gifts for Your Best Men

Updated on March 02, 2022 by Chris Bajda

The hard part is over, your lady said “yes”, and now it’s time to plan the wedding. In doing so, you will need your groom crew, so the first step on the list is completing the roster of awesome dudes you call brothers and make them agree to be your groomsmen or best man. While you may simply just ask and get it over with, the asking part will be more meaningful and memorable if you will put more effort into finding them great gifts to go along with your proposal. Below are ideas that might jumpstart more clever actions as you ask those men to stand by you as you wait for your bride.

Check out these 17 groomsmen groposal gifts and ideas along with items you may use:


17. The “Greasy” Card Proposal

The first step to this proposal is inviting your bros to a casual baseball watching, beer, and pizza night. Make them all believe that it is nothing more than a hangout of friends. Volunteer to buy the pizza and slip in the cards that say “You’re going to be my groomsmen. Okay, good talk. “So upon lifting every piece, which they might do at the same time, the message will be revealed and they will just as casually respond to it as you told, and not asked them to be your groomsmen. This is such a slippery and sure way to getting their “yes” through a card covered mostly in pizza sauce.

16. Scratch and Reveal

The trick is simple and does not need so much effort. Just do a random meet-up with each of your groomsmen or your best man and be sure to come to a moment of complete silence. Then randomly ask for a coin as you forgot to check the scratch card you got earlier that day. As they look for a coin, be ready to bring this card out. If at any point they insist that they don’t have a penny or what, have a spare hidden in the deepest parts of your pocket. Bring the scratch card out and have them scratch the three covered circles. Surely, even before the words are completely revealed they would have already said “okay” to you.

15. Knock for an Answer

Knock on the door of your groomsman or best man to be holding a plain white envelop with a card inside and theatrically add on a cryptic smile and look. Remember that the whole scenario will be dependent on your acting ability. Then, as your friend opens the door tell him you saw the envelope in front of his house and since it does not have any label you just picked it up. Make him believe that you think he just missed it on the porch. As he curiously opens it, he will slowly lose suspicions and gain excitement to say yes to rendering his service as your groomsman or best man.

14. A Home Run Groomsmen Proposal

The feeling of having hit the home run has been in your system since your fiance’ said “YES” to you. Now bring that same thrill as you hand over this MLB-inspired groomsmen proposal ticket and make their hearts leap for joy with the thought of having a front seat of all the fun and action. Well, they will have a front seat, your wedding! While this may be a nice and sporty trick for your best buds, you may level up your proposal by attaching an actual baseball game ticket along with this pseudo version.


13. A New Smoker Set on Display

Ask that smoking buddy of yours to join you as you check the latest smoker set in your favorite tobacco store. Of course, ahead of time, you will ask that store to place this set on display for him to see. And as you reach that place and as he sees the box, he will immediately notice his initials on the box and each item inside. Do your magic and tell him that this smoker gift set is specifically made for this best man or one of his groomsmen. He will take home a box filled with nice stuff and you shall bring home a “yes” from him.

Bet on a gift box set. Whether men would like to admit it or not, a proposal box or gift set of handpicked delights make their happiness meter rise and push them further to say “Of course, Bro!” to your proposal.

12. Chess to His “Yes”

Challenge your buddy to a friendly chess match and whoever loses gets to do a favor for the winner. Use this chessboard set without revealing its other contents. Towards the end of the game, whoever wins, opens the chess box and shows the inscribed flask with his initials. Winner or not, ask him to be your groomsmen and take home the chess set together with a flask, funnel, and shot glasses. Since his initials are already in the set, you are sure to play this chess in confidence that he will say “yes” in the end.

11. Tailor Fit your Proposal

Go to your favorite tailor shop to hand over this gift box and conspire with the staff. Ask your best man to join you as you have yourself measured for your wedding tux. As you are inside the curtained room fitting, have a staff hand over a black box and say that these are the accessories that might match your coat or tux of choice. Upon opening the box, he will see all the accessories a man will need for a wedding event, but the twist is, the box holds a card saying that those are for your best man who is holding the one reading the words.

NEVER SAY NEVER WITH SOMETHING CLEVER. Always include fun in your proposal as it may not only get you a “yes” but it will gain you a laughing buddy for life.

10. Wanted! Groomsmen/Best Man

First, use this dagger to pin a paper in a tree with your friend’s face drawn into it like a wanted villain with the words “Groomsman or Best man” below it. On top of the face must be a glaring “WANTED!” sign. Second, put a REWARD sign and the words “My friendship and brotherhood for life” across it. Then, take a photo of that scene and send it to your groomsmen or best man. Don’t forget to give a deadline saying, I need a “yes” or a “yes” before noon. (or be creative) Finally, wait for a yes and then give the dagger to those who did.

9. The Perfect Fit

Men do not usually give undergarments to each other, so the deed of handing this piece of garment will already be awkward and funny enough for your groom crew. Casually give it to them and make them open it in a public place and allow them to see that on the back it says “best man or groomsman”. The shame of flaunting a boxer briefin the crowd will immediately turn to pride and laughter as they realize your efforts to asking them to be a part of your wedding.

8. A Mischievous Addition

Just to add spice and clever touch to any funny proposal gifts you have in mind, place this card with a misleading message on top. Surely it will bring a shock and delight at the same time to your best buds as they get tricked into finally being allowed to get you a stripper only to be awakened by the tiny font messages that negate the idea. Make this an add-on or hand it solo to your groom crew in a public place, either way, it will be hard to say “NO” to this proposal card.

7. The “Naked Lady” Pitch

Some of your pals will just believe anything you say or show them, so for your proposal, leverage on that. First, on a normal sunny day, ask your buddy for a stroll. Second, tell him you bought a new set of shades and wear them immediately on the side that does not show the inscriptions. Upon placing it in your eyes, pretend that you are seeing something different. Create a story that you are seeing ladies in bikinis and trick your friend into checking it for himself. Once he wore it, reveal the point. Say that the shades fit him and he cannot take it off anymore as he is already your groomsman. That is like getting a “go” without even asking.

GO NEAT AND SWEET. Admit it, asking your pals to be your groomsmen and best man is a nice gesture. Try the consistency of asking them while handing over great  proposal gifts.  

6. Hook the “Go” from your Bro

If you and your friends love fishing, ask them on a fishing trip and offer to fix their hooks. Before throwing it on the sea, ask them to look closely at the inscription as you have it made specifically for the most amazing men in your life that you want to be in your groom crew. If it is a “yes”, challenge them to catch a fish using the hooks. Whether they do so or not, their agreement is already on your net.

5. “Yes” from the Wrist

Wear this square wooden watch and take a walk with your buddy. Along the way ask him if it fits you because it seems like it doesn’t and then quickly take it off. Ask him to give it a try and wear it. Even before he does, he will see the inscription behind it that says “best man or groomsman”. When he does, do your trick in asking him if he will say “yes”.

4. Horn Your Way to His “Yes!”

The deed is simple. Place this Buffalo Horn Mug in his ref or table and wait for him to notice it. Surely this intricately designed mug will stand out as he is not familiar with it as well. The curiosity will lead him to lift it and read the message at the bottom “Will you be my groomsman?” Write your name after so he will know who to say yes to.

3. Puzzle-in Your Proposal

If you ask your friends to solve this puzzle sober, there will be no fun in that. So ask them to drink a little before engaging in a nice puzzle-solving competition. Give each of your buddies their actual pieces so that towards the end it shall reveal an upfront proposal message. This neat and smooth way of asking them will need no more follow-ups but a straightforward answer, if they can.

2. Pour and Go

This one needs no dramatic asking or answering. On a baseball game, hand over these Baseball Bat Mugs to your pals and once they allowed beer to be poured down to it, that means it is already a “Go” to being in your groom squad. Using this every time they drink especially at your wedding will add a special touch to being a member of your elite crew.

1. Par-Tee for your Party

For your golfer buds, this is a unique and sweet proposal gift and gesture. Before the game, tell your friend that you bought a new set of golf balls and tee. Ask him if he thinks you must use it on the game that day. Whether he says yes or no, hand him the box and let him open it. The asking will be clear as day. So the next part is the answering. Tell him to use the ball and make a birdie and that will mean a “YES”. If he did not make it, well his name is on the box and the word “groomsman” is on the ball so, I believe you just pushed him into giving his groomsmen services a “go”.

Chris Bajda

About the Author

Chris Bajda is a renowned expert in gift selection, with a 15 year history of finding unique gifts. His insight into the art of gifting and staying on top of trends by his consistent presence at major gifting trade shows, including his annual participation in NY Now trade show in New York City and several other trade shows throughout the United States. Chris has built a reputation for his knowledge in finding gifts that leave a lasting impression.

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