The Bro Proposal: How to Ask Your Groomsmen To Be Part Of Your Wedding Day

While your wedding day may seem far off, the time leading up to your big day goes by faster than you think. Grooms should start planning on selecting, and proposing to, their wedding party about 8-10 months prior to the wedding. This gives your best man and groomsmen plenty of time to get everything in order for your big day, from making sure he has his suit to planning and booking your bachelor party. 

When planning your groomsmen’s proposal, you’ll want to consider what type of relationship you have with each of them. Are you a big group of friends that hangs together often? Are you all passionate about a particular activity or sport? Do you all live in the same area or are you spread apart? Whatever the situation, we’ve got great ideas for how to ask your groomsmen to be in your wedding. 

GROOMSMEN PROPOSAL GIFT IDEAS

The Proposal Kit 

This is a personalized box that says all things “groomsmen.” You can include traditional items like a flask (loaded with his favorite liquor, of course), a cigar, wallet, leather-bound notebook or journal, a fancy pen, koozie, and a bottle opener. Make it even more special by personalizing each item with their initials. If you want to veer from tradition, consider what you all have in common. Are your guys all about golf? Mountain or road biking? Poker? Load up the Proposal Kit with items that match the theme. 

The Starter Kit 

Similar to the Proposal Kit, the Starter Kit contains items that your groomsmen will need on your wedding day. Starter kits can include personalized cuff links, ties, tie clips, watches, and pocket squares. If you’re planning a destination wedding, your Groomsmen’s Starter Kit may include items specific to the area you’re going to. Think sunscreen, bug spray, sunglasses, a hat, koozie, swim trunks, and sandals or flip flops. 

The Personalized Flask and Premium Cigar 

For the sophisticated and traditional groom, you can never lose with a simple engraved flask and an elegant cigar. Consider filling the flask with a premium whisky that you know he’ll love. Pair the cigar with the liquor and your gift is complete. 

The Personalized Invitation

If your groomsmen live too far away to have an in-person proposal, or you just need to save some coin for the wedding, send a groomsmen-specific invitation. Include punchy fun lines like “Get Ready to Suit Up,” “Help Wanted,” or something more casual like, “Hey Man, Let’s do This.” Include the wedding date, location, and the name of your bride. If your wedding will take place at the beach or on a mountain, have your invitation match. You can send your invitation solo, or complete it with a groomsmen gift, like a personalized bottle opener or cigar. 

HOW TO MAKE YOUR GROOMSMEN PROPOSAL UNIQUE 

The Group Outing 

If all of your potential groomsmen live in the same area, consider a group outing that everyone enjoys. This can be as simple as a boys’ night out at your favorite bar. Or, if your group bonds over a specific activity, plan a day out to play. Book 18 holes at your favorite course, hit up your favorite mountain biking trail, plan a surf excursion, or go the extra mile with a weekend of camping. Present your gifts while on your outing.

The Bro Date

Maybe you want your proposal to be a little more personal. Take your bros out individually. Go out for a burger and beer or check-in at your favorite sports bar for snacks and the game. Present your gift and pop the question. We recommend the bro date especially for asking your best man to stand with you at your wedding. Not only could it be awkward to ask him in front of your other groomsmen, being the best man is a special honor. He’ll appreciate the extra thought and care you put into your request. 

The Double Date

Want to have your fiancé involved in the process to? Propose a double date with you, your fiancé, your groomsman-to-be, and his significant other. Reserve a nice dinner out at a fancy restaurant and surprise him with your proposal. Women love this kind of thing and will appreciate being part of this special moment. Even better - she will probably help out with planning the proposal! 

Now that you’ve got your wedding party on board, it’s time to start checking some other items off your groom wedding checklist, such as planning the honeymoon and purchasing your wedding band! Get with your bride and start thinking about where you might want to honeymoon and start browsing men’s wedding bands - but don’t get overwhelmed! The Hitched wedding band home try-on makes men’s wedding band shopping easy – Browse, test, and select your wedding ring from the comfort of home. Get started.

Photography: Becca Romero Creative