Ready to jump into the world of wedding planning and work on the fun task of deciding who your groomsmen for your wedding will be? Don’t sweat it because we’ve got you covered with exciting ideas on how to ‘pop the question’ to your best mates. Think beyond the ordinary groomsmen invites, and let’s add some zest to it, shall we?

Pondering over how to ask your buddies to be a part of your big day can be a highlight of planning the wedding. Here’s the deal: spruce it up with a groomsmen proposal gift—or, why not, multiple gifts! Adding a gift box to accompany your groomsmen proposal card is a great way to make your invitations feel extra special. Let’s dive into some unique gift ideas to make your groomsman proposal an unforgettable experience.

When should you propose to your groomsmen?

Ask your friends to be your groomsmen around three to six months before the wedding. This timing allows your groomsmen ample time to plan for any responsibilities, such as organizing the bachelor party, and ensures they can arrange their schedule around your big day. If your wedding involves significant travel or your friends have particularly busy schedules, send the groomsmen invitations even earlier.

What to Put in a Groomsmen Proposal Box

Nothing makes your best bros feel special like a groomsman proposal box brimming with goodies tailored to your pals’ tastes and interests. Be it for the golfing enthusiast or the budding mixologist, we have groomsmen proposal ideas for all your closest friends.

Why not try the ‘Suit Up Groomsmen Proposal Boxes‘? Tell your friends to gear up for the role of a lifetime with this pre-filled box, complete with a personalized flask, cool sunglasses, and funky dress socks bearing the coveted question. All set in a sleek black box, it’s a sleek groomsmen invite sure to impress.

If your pals are into whiskey, the ‘Whiskey Wizard Box‘ from Groomsday is one of the best groomsmen-asking ideas. Pair a bottle of bourbon with this gift box, and you’re all set for a great groomsman proposal. The kit includes everything your buddy needs to craft the best glass of whiskey at home, including a personalized glass and coaster.

Consider the ‘Mailable Groomsman Proposal Boxes‘ from Greetabl for long-distance groomsmen invitations. These fold-out boxes provide space for the all-important questions, photos, and a small gift. It’s like a little party in a box!

Don’t forget to send a nice card with each box. A thoughtful groomsmen card with your proposal gifts brings an extra personalized touch your closest friends will appreciate. All you need to do is choose your card, type your message, and let us know the addresses to send to (or choose from your free online address book). We mail everything so your groomsmen’s invites are as stress-free as possible.

Impressive Standalone Gifts for Groomsmen Proposals

We have plenty of unique groomsmen proposal ideas if you’re thinking of standalone gifts or planning to curate your own boxes.

How about a box of ‘Custom Golf Balls‘ or a ‘Touch Down Proposal’ for your sporty friends? Other great groomsmen-asking ideas include these ‘Groomsmen Shot Glasses‘ decorated with tuxedos, adding a formal and fun touch to your proposal.

For those who enjoy the finer things in life, ‘Monogrammed Handkerchiefs‘ or a ‘Personalized Leather Toiletry Bag‘ make excellent groomsmen invites. These ‘Scotch-infused toothpicks‘ are a unique (and flavorful) idea that leaves a refreshing taste after every meal.

Don’t forget the ultimate wildcard—gourmet candy. Sweeten the deal with a ‘Sugarfina Gourmet Candy Bento Box.’

Are groomsmen proposals a thing?

Absolutely! Asking your friends to participate in your special day is a joyous and unforgettable event. It’s about creating memories you and your buddies will cherish forever. So, enjoy choosing your gifts, pair them with nice groomsmen proposal cards, and get ready to celebrate your wedding with your closest loved ones!