Pop the groomsmen proposal with these "Will you be my groomsmen?" gifts. The hard part was finding the right girl, the easy part is finding a proposal idea that will get your best man and groomsmen to say ‘yes”.
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46 Best Groomsmen Proposal Gift Ideas in 2024

Trying to come up with a great groomsmen proposal idea?

Just when you thought you could finally take a deep breath and relax for a moment, it’s time to move on to your next job as the groom, coming up with a great groomsmen proposal idea

You came up with a great way to propose to your girl, now its time to figure out how you will ask your groomsmen.  From proposal boxes to funny cards, we have all the goods to make asking your guys in a fun and memorable way.

Below are 46 of the best groomsmen proposal gifts and ideas:

46. Spiral Your Groomsmen Proposal 

Groomsmen Proposal Football

Put a little gridiron in your gifting with a gift that won't fumble on your big weekend. Your groomsman will feel like a Super Bowl MVP when you toss your groomsmen a perfect spiral with this personalized football. How many gifts can you ask your man to run a deep slant to receive? Throw some laces in his hand with a gift that won't disappoint. 

To pull this groomsmen proposal idea off,  do the following:

  1. Buy the personalized football and have it customized with your groomsmen's names and "Will You Be My Groomsman (or Best Man)"
  2. Hop in your car and drive to your groomsmen's house.
  3. Send your groomsmen / best man a text that tells them to go outside
  4. Throw him the football.  (try to throw a spiral so your groomsman does not make fun of you)  
  5. Watch the smile on his face when he reads it (try to have someone ride with you to capture it on video)
  6. Hashtag #GroovyGroomsmen on social media when you post the video so we can share in the celebration with you! 

To see this groomsmen proposal idea in action, check out how @alleyrose5 pulled it off in this video on Tik Tok. 


Groomsmen Proposal Football

45. Chug to Accept Groomsmen Proposal

Another fun way to pull off a groomsmen proposal is put the labels and pictures below on a beer and make them chug a beer if they accept their role as a groomsmen (or best man) in your wedding party.  You can pull this groomsmen proposal idea off by getting together with your squad in person, or you can send them the beer in the mail.

Groomsmen proposal beer label

To pull this groomsmen proposal off,  do the following:

  1.  Buy the groomsmen proposal beer labels shown in the picture above, customize them with each guys name and "will you be my groomsman?" or "will you be my best man?" depending on their role in your wedding party..
  2. Go to the liquor store and buy your groomsmen's favorite beer (pick one that he can chug).
  3. Put the beer labels on the beer.
  4. Send the beer to your your groomsmen in the mail. Put a note in the package that tells them to chug the beer if they accept, and take a video of it.
  5. Ask your groomsmen to send you a video of him chugging so you know he has accepted your groomsmen proposal.
  6. Bonus: Once you get each guys video edit them all together and make 1 video that you can send to all of them and have as a memory for the rest of your life.  Hashtag #GroovyGroomsmen on social media when you post the video so we can share in the celebration with you!  

Check out the video below to see this idea in action.


Related: If you don't want to send a beer in the mail, grab them a groomsman shot glass and have them do a shot instead of chug a beer.

44. Put His Face On a Flask


Groomsmen Proposal Idea Caricature on Flask

How could anyone possibly say no to being your groomsman when you’ve gifted something like this personalized caricature flask? It doesn't get much cooler than throwing your groomsman’s caricature on a flask for your groomsmen proposal. Face on a Flask is a custom drawn caricature of your intended groomsman printed on a traditional 7-ounce stainless steel flask. This is the perfect way to ask the important guys in your life to be by your side for the big day.

43. Time To Suit Up Groomsmen Proposal

Groomsmen Proposal Watch


    With an accessory he can readily wear for your wedding day, you’re sure to get a resounding yes to make him one of your groomsmen. This personalized wooden watch groomsmen proposal box set is made of 100% authentic wood with no added chemicals. It features a Japanese quartz movement with a classic and simple design. It’s durable and long lasting you can be sure your groomsman will be able to use this for a long time on any occasion. It even has a 12-month warranty and offers repair services. Each watch comes in an eco-friendly box and personalized for each groomsman. You can't go wrong with this groomsmen proposal box set. 

    42. Take Your Groomsmen Axe Throwing

    Groomsmen Proposal Ax

    Take your future groomsmen out for a night of axe throwing and drinks. This  will allow your guys to relieve some stress while catching up with friends and reminiscing on good memories you’ve had together. Take your proposal to the next level and axe to the max by also purchasing engraved axes that you give your guys on the night you propose to them so they have a memento to help them remember your groomsmen proposal. Ask the employees to switch out their axes with these handsome hatchets. While it’s unlikely your groomsmen ever apply the throttle of this handheld howitzer.

    41. Groomsmen Proposal Scratch Off Card

     Groomsmen Proposal Card Idea

     It’s no ordinary card. The creative side is that you’re giving him a clue that it’s time to suit up with that scratch off groomsmen proposal card that will do the asking for you. It’s really one unique and classy way of asking him to be by your side on your wedding day. The card is made of white smooth heavy card stock and a black paper bow tie is attached to the front of the card with volume stickers. Watch the look on his face as he scratches off and read what’s written on this card. 

    Related: See more groomsmen proposal card ideas.

    40. Groomsman Proposal Rotating Box with Cufflinks

    groomsmen proposal cufflinks

    Your not crying, he's crying. Bring some man tears to your buddies eyes with this dressed up groomsmen proposal gift. With this rotating cuff link proposal box, you will be able to "pop the question" easier than ever before. Get your guys geared up for your big day in style with this high class groomsmen gift. Bonus points for getting down on one knee.


    39. Ice Breaker Groomsmen Proposal

    Ice Breaker Groomsmen Proposal Gift Idea

    Asking your Groomsmen to step up and join you on your big day can make you nervous.  This groomsmen proposal gift set is a great way to break the ice, literally!  Roll up this Time To Suit Up T-shirt with your preferred bottle of alcohol that you expect your buddy to "Chug to Accept" once opened! Get your groomsmen ready for what is to come with this fun gift that is sure to get the party started!

    38. Groomsmen Proposal Bomb

    Fun Groomsmen Proposal Set

    Fun, simple, and effective, the Groomsmen Proposal Bomb is a great way to propose to your wedding party.  Grab this set, that comes with a personalized shot glass and a label inside a cool black box.  Go to the liquor store and pick up a half pint of your buddy's favorite booze, and then slap the provided label on the bottle and do a shot with him the next time you see him.

    37. Golf Ball Groomsmen Proposal

    Golf Groomsmen Proposal

    This "will you be my groomsmen?" gift set includes a customized golf ball inside the box that says, “let's par-tee” on it.  It is an awesome groomsmen proposal idea if we bonded over our mutual enthusiasm for golf.

    36. Groomsmen Proposal Gift Box

    Fun Groomsmen Proposal Gift Box

    Fill the flask with his go to liquor, send him the box or hand deliver it and make sure someone is recording for the record. This groomsmen proposal gift set will hit just the right note between you and the guys. They will know how much you mean to them while being called for duty.  For an added punch, get all the guys together, have the closed boxes (with their names on top) there and have them open them together.  Be sure to have a bottle of your favorite booze handy to fill up the shot glasses with for a toast that you will remember for the rest of your life.

    Related: See more groomsmen proposal gift boxes.

    35. Home Run Groomsmen Proposal

    Baseball Groomsmen Proposal Gift Idea

    Hit a home- run with guys of all ages! Whether they are helping you out on your big day as the Usher, Groomsman or just a constant shoulder to lean on, commemorate their contribution with our I Do Crew Baseball. No guy can resist this gift.

    34. Put It In A Cooler

    groomsmen proposal cooler

    In the words of the great Ciara a cold one brings all the boys to the yard, and damn right this one is better than most. This insulated and personalized cooler will keep his drinks cold and your groomsmen happy. Just fill it up with some of his favorite beverages, present it, and wait for the screams of joy.

    33. Tie the Knot Groomsmen Proposal

    Tie the Knot Groomsmen Proposal

    Get your groomsmen together for the most important knots of your life! The Knotty Groomsmen Proposal is simple, elegant, and stylish! There is no better way to ask them 'will you be by groomsmen' than to provide them with this great gift set that they can continue to use!


    32. Tell Them It's Time to Suit Up

    groomsmen proposal gift set

    Kill two birds with one slick groomsmen set. Pop the question to your favorite guys while making sure they don't look like slobs on your big day. No guy will be able to resist the idea of joining your debonaire looking squad. Watch the smile grow ear to ear as you pop this groomsmen set in front of him.

    31. Never Let Him Forget an Embarrassing Moment

    Fun Groomsmen Proposal Idea


    You've been through a lot with your buddies, odds are there are a few moments in time that you guys always go back to when you need a good laugh.  If you were lucky enough to snag a picture of that time, the Pic on the Pint is a great way to get a great laugh out of him before you get sentimental and pop the "will you be my groomsmen" question to him.  

    Another great option is the just get a pic of your buddy or even a picture of the two of you together.  The makers of this item can put any text that you want to put on the glasses on them.  

    30. Send Them Groomsman Underwear


    Grab these boxers that have "groomsman" or "best man" on them and send them to you guys in the mail and attach a card that asks them to be your groomsmen. It will undoubtedly get a good laugh out of them and you can ask your guys to wear them on your wedding day, which will make for some funny pictures.

    29. Put A Koozie On It

    groomsmen proposal Koozie

    What guy can so no to this indecent groomsmen proposal!? Like the Nick Fury of Grooms to be assemble your squad. Only the best and brightest for your big day. So can they hang?  Your groomsmen will be toasting you and your leading lady for years to come with this awesome groomsmen proposal gift. This stainless steel koozie is double walled ensuring dry hands and cold beers all around.

    Related: If you like the idea of getting a groomsmen proposal card but want to see a few more, check out these groomsmen koozies.

    28. Draft Your Groomsmen 

    This is you chance to show these men how much you value their friendship and how grateful you are for the chance to journey with them through life's ups and downs. . Go from round to round drafting your friends by listing their talents and strength as groomsmen. This is a good way to roast your friends by drafting them late and coming up with fun nicknames and numbers for their jerseys. Ask them in a most unique way through an Ultimate NBA Draft

    Check out this video to give you the idea: 

    27. Propose To Him With a Gift Box Set

    Groomsmen Proposal Gift Box

    Like a groomsmen gift from the gods, this groomsmen proposal gift set has it all. This custom-made gift set will equip your groomsman to be prepared for whatever the night has in store for him. With a variety of items packed neatly inside this round matte black box, you'll thank your groomsmen for their service with a sampler style list of items he'll use no matter the occasion. The only thing missing is a knife, (that's probably for the best).

    26. Make Them a Groomsmen Caricature

    For a hit groomsmen proposal gift make them a custom group groomsmen caricature that will be sure to give them a good laugh and either ask them by texting the picture to them or printing it and delivering it in person.

    Another super way to ask your boys to have your back at the altar is to send each of them asuperhero undershirt. Think long and hard about each of their “abilities” and assign them to the superhero they most identify. Which Groomsman is quick with one liners.... Tony Stark. Which Groomsman do the ladies all love but he doesn't even know it...Thor. The possibilities are endless!  Attach a note describing how they’ve used their powers to enhance your life, and “Pow!” you’ve just saved the day! Personalize the back of these shirts with their last name or wedding title and they’re sure to be a hit.

    Related: See more funny groomsmen gift ideas.

    25. Enlist Your Groomsmen Card

    Groomsmen Draft Card

    EXTRA EXTRA READ ALL ABOUT IT!!! Single man getting married, groomsmen service required. Propose to your groomsmen in style, with this groomsmen proposal cardthat will complement any of our groovy gifts or just a great way to ask your guys to be in your wedding party.Don't stand alone in front of the crowd, enlist a great team to stand by your side on your wedding day.  

    Related: If you like the idea of getting a groomsmen proposal card but don't love this one, check out these groomsmen proposal cards.

    24. Groomsmen Leather Personalized Poker Set

    Nothing says "Boys Night" like poker night. Your future husband and his groomsmen can enjoy many fun-filled nights of poker and celebrations when they play out of our Personalized Groomsmen Leather Poker Set. Personalize this poker set with any title, initial, any name and any date.

    23. A Bottle of Booze with a Custom Groomsmen Proposal Label


    Groomsmen Proposal Booze Label



    A bottle by itself is the most pedestrian of gifts, but slap on a label that personalizes the flask like it’s only meant for your groomsmen and shazaam, you have gift magic! The BroLabel is the perfect way to ask your buddy that important question. Treat your favorite guys to a bottle of their favorite sauce, but with a message they can’t ignore. This flask is going to find a special spot in their man cave bar and be used for years to come.

    Related: See more fun groomsmen labels.

    22. Make A Video for Them

    Make a funny video and then send it to all your groomsmen. A great touch is to figure out a fun way to make fun of each of your groomsmen in the video. There are a few different angles you can take with your video, below are two good examples.

    You all love watching movies. So why not make your groomsmen proposal as cinematic as possible by coming up with a short film and ask your favorite buddies to have your back on your wedding day. 

    21. Do a Shot Together

    Groomsmen Proposal Shot Glass

    Presenting your best man and groomsmen with these personalized shot glasses would be an ideal way to ask them to be an essential part of your big day. Or better yet, present the shot glass to him in a personalized box set and put a pint of your favorite alcohol in it.  Once they receive these shooters you can all toast to your bachelorhood one last time before tying the knot. 

    20. The Indecent Groomsmen Proposal Gift

    Blue Groomsmen Proposal Box Set

    You popped the question once, now you need to get down on one knee for your guys. No sweaty palms about this proposal though, no guy can say no to this groomsmen boxed set. Filled with items your groomsmen can you use from the bachelor party to the big day and beyond, this 5 piece set is the perfect way to get your best friends to stand beside you as you marry the girl of your dreams.

    19. Send Them a Funny Text Message

    Great Groomsmen Proposal Texts

    You can get this over with even faster, if you so choose: you aren't proposing to your girlfriend again, after all. Send a text message if you are really a man of few words, be sure to confirm that he's around during the date you've set for the wedding. Below are a few ideas for text messages you can send:

    1. I know you don’t know how to tie a bow-tie, but will you be my groomsman anyways?
    2. I need you to hold my hair while I throw up at my wedding. Will you be my groomsman?
    3. Make them a meme using ImgFlip
    4. I know you like free food, liquor, and parties. Be my groomsman for access to all three?
    5. This is me, asking you, to be my Groomsman. There will be beer.
    6. You've always been great at spotting me in the gym, I was wondering if you would be able to spot me on my wedding day?
    7. Bro, I only get one decision at this wedding, will you be my groomsman?
    8. I found my woman, but I still need my boys. Will you be my groomsman?
    9. Hey man, its time to suit up. I'm getting married, will you be my best man?

    18. Suprise Them at the Golf Course 

    Just when he thought it's just another day with you at the golf course, he'd be happy to say yes to your surprising and of all the places way of proposing to him to be one of your groomsmen. 

    Check out this fun video: 

    17. Create a Mini Bar Boom


    jar of nips

    He enjoys the occasional drink, so help support his habit.  Make sure you choose his favorite drinks and he will never forget this unique way of asking him to be your groomsmen, he'll thank you once he is drunk. Ask him to be your groomsman by giving him this minibar in a jar

    16. Tickets to a Sporting Event

    I know earlier we downplayed the whole jumbotron idea, but assembling your guy gang for your favorite concert or to root on your local sports team is a great way for male bonding. So grab some tickets and bring the most critical men in your life together for an event and it's a fun and easy way to pop the question to all of them at once.  

    15. Take them to a Cigar Lounge

    Invite the guys out to a cigar lounge and ask the proprietor to add a note to each of their cigar choices, asking them to be your groomsman. Having all the guys in one spot without any distractions will allow you to relive old memories, and thank them for always being by your side. To make it even more classy, get them a personalized cigar gift to present to them and thanking them for always being there for you.

    14. Setup a Pub Crawl

    Pick a day or one for each of them with the perk of drinks at your local bars and you have the best way to ask your buddies to be your groomsmen. You can access multiple bars with one party pas and take advantage of drink specials at the same time. Pub Crawl are organized in cities all over, you won’t have a hard time choosing the perfect bar to ask them once they are all drunk.  

    13Fun Groomsmen Bottle Opener

    bullet groomsmen bottle opener

    Take the squad out hunting or to the range and bro pose with a literal shot.Then pop the question with an engraved bullet bottle opener.  Each one is made from a once-fired .50 caliber military bullet.  No guy can resist this testosterone filled groomsmen proposal.

     Related: If you like the idea of a bottle opener for your groomsmen but would like to see more options check out some of our favorites here.

    12. A Cigar with a Custom Label

    Will You Be My Groomsman Cigar Ring

    Gather your man group for an outing on the links and gift a cigar for the day. The message will be as clear as the greens on an approach shot when they read the personalized label wrapping their stogie. Pick your favorite colors, and label them according to their names and wedding titles. This is a groomsmen proposal gift that will turn heads and get the boys revved up for the big day.

    11. Class It Up With A Decanter

    groomsmen personalized decanter

    This is for the gents or wanna be gents. Gone are the days of him pounding his jack and coke out of red solo cups and proudly displaying his cheap liquor bottles, help your groomsmen out  while popping the question. A quality decanter will set the tone for the main event, personalize it for bonus points. They will definitely be ready to rock their suit and ties after toasting you and your lady with a few pours from this. Go the extra mile and fill it for them and you will be hearing "I do's" all around.

    Check out the video below to see this groomsmen proposal gift in action:


     10. Its Time To Suit Up Proposal Box

    Every guy loves boxes, and when your guys open this groomsman proposal bomb box they will have a message waiting for them that asks them to be your groomsman or best man.  They will be pumped you are proposing to them, and even more psyched to find an awesome knife and shot glass inside the box. For an added punch, get all the guys together, have the closed boxes (with their names on top) there and have them open them together.  Be sure to have a bottle of your favorite booze handy to fill up the shot glasses with for a toast that you will remember for the rest of your life.


    9. Drafted Groomsmen Proposal Beer Mug

    Drafted Groomsmen Proposal Beer Mug

    Do you hang with a real beer drinking crowd? If so, these personalized beer mugs will do the trick. Invite your boys over and slide these 25-ounce steins across your man cave bar to each of them. Their smiles will be enough for you to know “They’re in!” What’s better than having a drink with the boys? Celebrate your big news with an ice cold beverage from one of these bad boys.


    8. Cuff Links to Wear on Wedding Day

    Will You Be My Groomsman Cuff Links

    What better way to ask your loved ones to be your groomsmen or best man than with this box and cuffs. This is a heartfelt thank you to be worn the day of the event and then cherished for years to come. These Personalized Silver Oval Cuff Links will add that subtle touch to the men's formal wear on the day of your wedding, and they serve as a wonderful gift that can be used in the future for other special events. So ask your men in style with these traditional wedding cufflinks that are silver plated and feature a non-tarnish finish.

    7.  Humidor with Cigars that You Can Smoke Together

    Cigar Groomsmen Proposal Idea

    It’s not every day that he will have the luxury of lighting up a cigar, not alone, but with his best buddies. Imagine the delight in his face seeing these cigars! Let him have that luxury with this gift as you ask him to be your groomsman with a note that says "Wait to light these up till my wedding day." Your wedding is a perfect occasion to indulge himself with his favorite friends in the world. Have the box engraved with his name, role, and wedding date to make it extra special for him. It’s one thoughtful groomsmen proposal gift he will surely remember you by.   

    6.Will You Be My Groomsman Mug

     groomsmen proposal funny mug

    Looking for a creative and funny groomsmen gift?  If you want to pat your groomsman on the back with a thank you for being a friend, then do it with a gesture that counts.  A stein is a stein is a stein, but not when you put a super cool likeness of your buddy on it.  It's only then that your tall gorgeous drinking glass becomes a stage for self-adoration, all while chugging down your favorite frosty one.  Who knew one could enjoy man's favorite past time out of a mini version of themselves.  Now that, men, is a super cool groomsmen gift idea.  

    5. Get Down On a Knee (Again)

    Get stupid and get down on one knee and ask them to be your groomsmen just like you did when you asked your fiancee. If executed correctly it will make for a funny memory. Check out the video below to see it in action.



    4. Grooms Crew Shirt 

    Groomsmen Crew Shirt

    This Groom Squad Sweatshirt is perfect for groomsmen and ushers. The best man tasked with getting wedding attire for the bachelor party will love these grooms wedding designs. Perfect for ring bearers, ushers and father of the bride. 

    Related: See more fun groomsmen shirts.

    3. Sing To Your Groomsmen

    Got a gift for rhyme and rhythm? Write a quick, possibly silly song that chronicles something funny you know about your friend or some of the dumbest things you've done together. Even if you keep it light, writing a song is a pretty great way to show your groomsman that you value their friendship and want to keep him around. Extra points if you can figure out something that rhymes with "groomsman"... "You're the best at playing Doom, man... will you consider being my groomsman?"

    It might be hard to pull off something with this product quality, but if you and your fiance are up for it you can use the video below for inspiration.

    2. A Celebrity Shout Out

    For $95, give your groomsman the celebrity treatment by using Cameo to pop the question! This app allows you to book a celebrity of your choosing to record themselves reading the text you provide. The celebrity will record the video and send it back to you. All that’s left is to send the videos to your groomsmen of the celebrity asking the big question. With celebrities like Antonio Brown, Ice T, and Matt Hasselbeck, you’ll take the cake for best groomsmen proposal of all time.

    1. Wearable Groomsmen Proposal Box Set

    Wearable Groomsmen Proposal Gift Box

    Asking him to be your groomsman will be as natural as possible as you present him with this personalized proposal box set that has him covered for his all-day everyday needs. This set comes with 5 gifts neatly placed in a personalized VIP box.

    Related: See more groomsmen box sets.

    Memorable 'Will You Be My Groomsmen' Ideas

    No matter how you choose your groomsmen proposal, make sure you find the best gifts possible for them - they deserve it! Whether you use gifts to get the guys on board with joining your wedding party or save the gifts for thank-yous after the reception is shut down, they'll appreciate whatever you choose for them, in addition to free food, getting to look really classy for a day, and hanging out together afterlife and adulthood makes it harder to find time to do so.

     And if all else fails, hold an audition for a role as a groomsman in your wedding party:


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