One of the best parts of wedding planning is bringing together those special friends who’ve always had your back. You’ve laughed, lamented breakups, nursed hangovers, and gotten into good-natured trouble together. They’re your people, so it’s a big deal to ask them to stand beside you as you pledge a lifetime of love and commitment to your other half. But how do you approach this significant question to do it justice? We’ve compiled 19 groomsmen proposal ideas—and the best groomsmen gifts—that’ll help you ask the question in a way that’s poignant and festive, and bonus points if you can get your buddies to shed some tears.
Tip: To ensure your groomsmen don’t think their role is just to party, make a plan to communicate how you want them to support you leading up to your big day. While managing a bachelor party is usually one of the expected tasks, you can also remind your best man to write a speech, ask all the guys (and maybe some gals) to have their outfits by a certain date, request their support for wedding day setup, and other expectations you may have.
1. DIY Gift Set
Show your platonic love by putting together gift sets containing an assortment of handmade offerings. Some of the best DIY groomsmen gift ideas we’ve seen include shaving cream, beef jerky, salsa, leather mason jar sleeves, and wood slice serving boards. While it’s fine to make all the groomsmen the same gifts, it might be nice to make your best man something extra special that speaks to your shared history. For example, a framed map with a pin in each location you’ve traveled to together is a great gift and a nice gesture.
2. Monogrammed Beach Towels
If you know your bachelor party, or wedding, will be somewhere beachy, drop the hint by gifting each groomsman their own monogrammed towel. One of the best parts of this groomsmen gift is there won’t be any confusion about whose towel is whose. Plus, you can easily find Etsy creators that can whip up this personal touch idea in no time.
3. Groomsmen Proposal Card
For grooms that have a way with words, add a personal touch by crafting Will you be my groomsmen? proposal cards that include handwritten notes expressing why each buddy makes the cut. Or, you can skip the wordsmith-ing thing and just give them a printed proposal card that comes with a cigar, a favorite groomsman treat.
4. Video Proposal
One of the most creative groomsmen proposal ideas is splicing together a video of your friends’ greatest (or funniest) moments, replete with your witty commentary, that ends with your pitch for why you want them in your wedding party. To make sure you can enjoy your potential groomsmen‘s expressions as they watch your handiwork, either show them the video when you’re hanging out one-on-one or create one video for the group and invite all the guys over for a video-viewing party.
Make sure all your best friends walk down the aisle in style by gifting them cufflinks that complement the groomsmen garb you’ve selected, especially if it’s a tuxedo and bow tie getup. To take it up a notch, you can even have the cufflinks monogrammed with a personalized label.
6. Treasure Hunt
Inject some fun and adventure into your groomsmen proposal by having all your special people partake in a treasure hunt at a go-to hangout spot. Have them start at a set location featuring a poster board with a clue for the location of the next clue. Though you shouldn’t be too obvious with your clues, make sure they’re not so hard either that the group never makes it to the treasure: you down on one knee.
7. Keep It Traditional
Who said proposing with a rose and a small box is just for marriage proposals (and The Bachelor)? See if you can make your best blokes tear up, or at least bust out laughing, by giving them the ultimate shock as you get on one knee. While you’re on a friend date, assume the proposal position and pull out a rose and that cufflink box, from the previous proposal idea, for a groomsman gift that’s sure to awe.
8. Customized Beer Mug
Why not gift your groomsmen something that’ll remind them of you—and all the fun they’ll have during your wedding? A beer mug with their caricature on it or flask engraved with their initials are thoughtful options that are sure to put a smile on their face as they say yes to your groomsmen ask.
9. Groomsmen Proposal Getaway
One of the most extravagant and memorable groomsmen proposal ideas is a trip to a destination that has special meaning for you and your nearest and dearest. If you can’t swing a full-on vacation that includes airfare and plush digs, shoot for a weekend camping trip to an adventure-filled spot.
10. Celebrity Cameo
Imagine your friends watching a video of one of their favorite celebrities asking them to be one of your groomsmen. Milestone moment, right? All you have to do is select a famous personality on Cameo, send the message you’d like them to record, pay a reasonable fee, and bam: you have one of the most epic, creative ways to propose to your side of the wedding party.
11. Box Set of Keepsakes
A thoughtful way to ask Will you be my groomsman? is to create a personalized box set of keepsakes—such as photos, keychains, beer bottle caps, and other mementos—from your friendships with each of your soon-to-be-groomsmen. Then, complete your proposal box set by including a groomsman can cooler or shot glass that allows you to ask the question without having to say a word.
12. Bow Ties
One of the best groomsmen proposal ideas for groups that enjoy eccentric attire, get a wild bow tie for each of your groomsman. When they give you a Why are you giving me this to me? look as you hand them the accessory, pop the question. But if your fiancé isn’t down with your groomsmen donning quirky bow ties, you can reserve them for the bachelor party.
13. Jumbotron Proposal
Most major sporting events feature a jumbotron that can display personalized messages for a fee. For a unique groomsmen proposal gift, why not stoke out your sports-loving bros by treating them to a game and asking your big question on the big screen?
14. Groomsmen Boxer Briefs
Get cheeky (pun intended) when asking your buds to be your groomsmen by passing out boxers with groomsman printed on the back. This gift might even help them create a classic PG-rated “mooning” pose during wedding photos.
15. Superhero Shirts
Friends that live for the next Marvel or DC movie will appreciate shirts featuring the emblem of their favorite superhero. And like the proposal idea above, you can all wear the shirts under your wedding attire and share a Clark Kent moment on your special day.
16. Bachelor Party-Themed Gift Box
Get your boys ready for your bachelor party by putting together a gift box that serves as a survival kit for the shindig. You can include items like a bottle opener, mini alcohol bottles, a stainless-steel flask, hangover pills, a pint glass, electrolyte packets, antacid, Advil, eye drops, mouth wash, sunglasses, and anything else you think will elevate the party or morning-after recovery.
17. Personalized Booze
Start your groom-groomsman relationships off with a bang by purchasing a bottle of their favorite alcohol and slapping a custom label on them. Plus, Etsy offers a variety of label options so you can find the perfect fit for your unique gift.
18. Photo Album Playing Cards
One of the best groomsmen proposal ideas, if poker is a bonding activity between you and your buds, is to gather your favorite photos and have a customized deck of cards made for each of them. But make sure that within each deck, you include a photo of yourself holding up a Will you be my groomsman? or Will you be my best man? sign.
19. Tie with a Tutorial Booklet
If neckties will be a part of your groomsmen getup, you might as well kill 2 birds with 1 stone by gifting them ties that’ll serve as your proposal gift—and get them one step closer to completing their wedding duds. And because few people know how to tie a tie properly, you can include a booklet on how it’s done.
Because you’ll probably want to show off your great groomsmen, a wedding website is a perfect way to feature a photo of each and a blurb about how and why they made your exclusive list.
Bailey Gaddis is a travel writer and author of Feng Shui Mommy: Creating Balance and Harmony for Blissful Pregnancy, Childbirth, and Motherhood. In addition, she works as a childbirth preparation educator and birth doula who supports mothers-to-be and new mothers. She is also a regular contributor to media outlets including Disney’s Babble, Working Mother, Pregnancy & Newborn, Huffington Post, Cosmopolitan, Redbook, and Woman’s Day. In addition to her childbirth-prep work, she volunteers for families in need of postpartum support. She lives in Ojai, California.