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10 of the Best Groomsmen Proposal Ideas

You've done the hard work, you were able to get your lady to say yes, its time to ask your wolf pack if they'll stand by your side on your wedding day.  Giving each of your guys a token gift when you propose to them is a great way to pop them the question.  Get your future groomsmen one of these gifts and come up with a fun way to propose to them, and you'll be sure to impress your guys and get a yes out of them too.  While it never hurts to break the bank and get your groomsmen an extravagant gift, a small gesture like a bottle opener or bottle of booze will do the trick. Below are 10 of our favorite groomsmen proposal ideas:

1. Print out a screenshot of a suit shop near your groomsmen.

It definitely is a unique way of asking him to be your groomsman. Just make sure this does not end up making him think it’s just another marketing strategy of the nearest suit shop in his place. It sure not need to end up in the trash just make sure you write at the back of the screenshot. Let him know why you want him to be standing with you on your wedding day. Don't forget to give him a timeline to suit up. You certainly want him to be stylish and punctual. This may be an informal yet funny way to ask your groomsman.

2. Send them a humidor of cigars.

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 gift he will surely remember you by.   

3. Create your own comic book. 

This is one fun and unique way to ask your groomsman by creating your own comic book. Fill it with you and your friend’s best moments and have it finish with him standing next to you on your wedding day. Let your creative juices flow by writing stories, adventures and even sketching out masterpieces. It comes with plenty of room for drawing at size 8.5x11. It is designed as a sketchbook but comes with a lot of templates for drawing your own picture and adding details. It also has several pages with conversation bubbles and sayings you can cut out and include in your book.      

4. Create a Mini Bar Boom

He enjoys the occasional drink and giving him this gift will certainly satisfy that craving. Make sure you choose his favorite drinks and you can be sure he will never forget this unique way of asking him to be your groomsmen. Every one of your groomsmen gets to select his preferred drink and just enjoy each other’s company on your wedding day. Ask him to be your groomsman by giving him this minibar in a jar. You can even come up with a themed mini bar in a jar that can match your wedding. Don’t forget to indicate the date when the bar can be opened.   

    5. Send your groomsmen a fun wedding shirt.

    Define cool as he wears this groomsmen shirt. Whether he’s relaxing at home or going out, this trendy tee would absolutely make him feel good and look better. Paired with his favorite jeans and shades, he’s ready to just hang out with friends or party all night. He will never have to think twice if this accentuates his cool choice. “Cool” has never been this stylish and comfortable. 

    6. Send your guys a drink Advent Calendar leading up to the wedding day.

    How fun is this gift? With your groomsmen given a chance to take a shot each day leading up to your wedding day, he will be the happiest guy to be asked as one of your groomsmen. The wine advent calendar is all kinds of luxurious. Each window holds a different quarter bottle of wine (or bubbles) from all over the world. It’s one expensive gift, so save it for the nearest and dearest people who’ll really appreciate it.


    7. Create a pub crawl for a guys weekend.

    Choose a specific day or one for each of them with the perk of drink specials at your local top bars and you have the best way to ask your buddies to be your groomsmen. You can access multiple venues with one party pas and take advantage of drink specials at the same time. Events of Pub Crawl are organized in cities all over the country so you won’t have a hard time choosing the perfect venue to ask.  


    8. Create a hangover kit for your groomsmen. 

    Ask your favorite buddy with a note that says "Your service is required as a Best Man, this kit may be needed afterward.” This hangover set includes custom printed “Team Grooms-Name” socks (obsessed) from sock prints, a cigar, spicy nuts, a little alcohol, of course, the Hangover Kit and a Zippo.


    9. Send your groomsmen a Barber box.

    He would really be needing a clean-cut, dapper look soon. But first, ask him to be one of the chosen few who would be standing beside him as he says “I do.” Add a note that your guys need to be cleaned up and looking classy by your wedding date and your proposal gift is here to help. This set includes an Edwin Jagger DE89bl razors, Van Der Hagen shave kit, empty cigar box, and mini bottles. It also comes complete with engraving.

      10. Tell them you want them like Uncle Sam

      He will certainly be surprised getting a door to door delivery from you when there’ really no occasion at all. Ask him to be your groomsmen as you let your creative juices flow by coming up with this “Uncle Sam, I Want You” poster. This unique and tech-savvy way of asking him will definitely not be forgotten easily and one he could always remember as he makes this poster a permanent collection on his wall.