How to Ask Your Groomsmen to Be in Your Wedding

groom and groomsmen wearing tuxedos with white jackets and black pants — Photo by Hana Gonzales

The people you choose to stand by your side during your wedding ceremony aren’t just there for show: They are the ones you’ve counted on through thick and thin (and wedding planning), and the best friends, brothers, or cousins who have always supported you. And while you may be tempted to shoot each man a quick text asking him to join your lineup of groomsmen, this is an occasion that calls for a little more effort.

“Whether they are family or chosen family, these are usually the people who are closest to you. Often, they have also seen the relationship with your fiancé grow from first introductions to wanting to spend your life with them,” says wedding planner Carina Van Son of Sinclair & Moore. “Whether it’s a heartfelt conversation or a big gesture, doing something extra tells your groomsmen just how important they are to you.”

What's more, though a gift is never required to go along with an invitation to join your wedding party, coming up with a thoughtful item is an extra personal touch your party will appreciate. “If possible, it’s great to give them something they can use and enjoy versus a trinket,” adds Van Son. “This can be anything from time together, heartfelt words, or something you know they’d love or have wanted.”

Meet the Expert

Carina Van Son is a lead wedding planner and designer at Sinclair & Moore, a Seattle-based event planning company.

To make your "groomsmen proposal" process as seamless as possible, we asked Van Son to help us highlight 30 creative ideas to consider when "popping the question" to your friends. Read on for more, including a timeline to follow when asking your groomsmen to stand by your side on your big day.

The Ideal Timeline to Ask Your Groomsmen

While there’s no specific “right” time to ask your groomsmen to join your wedding party, Van Son encourages couples to get their bridesmaids and groomsmen sorted as early as possible. “People love to plan, and your wedding party will love to help too!” she says. “The sooner you ask them, the sooner they can jump in.”

That said, while some groomsmen—like those in your immediate family—may be willing to commit to any date or venue, you should be able to provide all the men with your wedding date and general location when you ask them to participate. (This prevents any later dropouts from friends who didn’t realize you’d be expecting them to travel to Fiji for a destination ceremony.)

Another tip? You can invite any number of men to join the wedding party; the number may match the number of attendants on your fiance’s side, but that’s not a requirement. Consider close friends, family members, and future in-laws; many grooms also invite their fathers, grandfathers, uncles, or future stepsons to join them at the altar. Sisters and female friends can also participate as groomswomen, to boot.

groom and his groomsmen posing for wedding portraits outdoor — Photo by Niven Weddings

30 Gifts and Other Thoughtful Ways to Ask Your Loved Ones to Be Your Groomsmen

Ready to start the groomsmen proposal process? These ideas—from travel accessories and destination wedding essentials to custom jewelry and event tickets—offer something for every groomsman (or groomswoman).

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Just Do It

Inviting a friend or family member to join your wedding party doesn’t have to require a huge investment of time and creativity: You can just ask. “Meet up with each prospective groomsman one-on-one over coffee, lunch, a drink, or on a hike,” says Van Son. “Focus on the intention of asking each guy to step into this important role for your important day.”

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Get Active

If you like the idea of asking in person but want to make the moment a little more memorable, pop the question while on the slopes, the links, or during another shared pastime. “Treat each guy to a day out doing an activity that has a special meaning for you both: golf, the driving range, paintball, pickleball, skiing,” says Van Son.

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Plan a Night Out

An evening out with your best mate can also present a prime opportunity for inviting him to join your wedding party, says Van Son. Secure tickets to see your home team take the field, your favorite comic take the mic, or the band you’ve both loved since high school take the stage.

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Ask Them to Dinner

If time and distance make it hard to plan one-on-one activities with each of your groomsmen, plan a “man meal,” says Van Son. “Gather all the guys together at a favorite restaurant, and ask them all at the same time,” she says. A bonus: The food-and-beverage setting makes it easy for you to raise a glass to all their friendships.

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Throw a “Wedding Party” Party

Share the spotlight with your partner by asking all of your attendants at the same time. “Bring the entire bridal party—groomsmen and bridesmaids—together for a fête and ask them to be a part of your big day,” says Van Son. “Your gathering could be a simple, casual affair, or take it up a notch: Host a chic cocktail party, or make it something fun and kitschy, like ‘Bad Vintage Wedding Attire’-themed.”

groom posing with his groomsmen — Photo by Hipster Wedding

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Gift Them Signature Cocktails

Create a signature cocktail for your wedding party—or one for each of your groomsmen—and prepare for plenty of toasts by giving each man the key ingredients. “Who says signature cocktails should be limited to just the wedding reception and just the couple?” says Van Son. Her recommendation? A classic Old Fashioned. Fill a gift basket or box with Luxardo cherries, local bitters, mandarins, and brown sugar cubes; then add a specialty ice cube mold designed for whisky, she says.

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Preview Your Location

Asking your groomsmen to join you for a destination wedding? “Gift a coffee table-worthy travel book of the place the wedding will be located,” says Van Son (she likes colorful versions from Assouline), and help your friends and family get acquainted with the area’s most charming spots.

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Help Them Prep for Your Wedding's Locale

Prepare your party people for an extended trip to a foreign country with a book of phrases in your wedding location’s local language. Van Son suggests Penguin Phrasebooks in French, Portuguese, German, Italian, and Spanish, which can train your friends to tackle every travel situation, from lunch in Madrid to lost luggage in Rome.

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Gift Locally-Inspired Treats

Travel guides and phrase books can also anchor a bigger gift that ties into a destination location: Look for specialty snacks, drinks, and postcards that will kindle even more excitement for the upcoming trip. “Getting married in France?” says Van Son. “Add a French travel book to a bottle of Bordeaux and a baguette or croissants.”

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Make It a Team Effort

Inviting a friend or family member to join your wedding party doesn’t have to be a solo task, especially if the prospective attendant is a brother or bestie who’s close to both partners. “Ask him together, and share why it would be meaningful to both of you for him to be a part of your day,” says Van Son.

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Offer Up an Accessory

Offer up a practical accessory your future groomsmen can use during your wedding weekend or pre-wedding parties, says Van Son, whether that’s attending your bachelor party by the lake or bundling up for a cold-weather football game. “It can be as simple as sunglasses in the summer or a nice beanie for the winter,” she says.

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Gift Them Their Favorite Foods

If the way to your best man’s heart is through his stomach, hit the mark with sweets and treats that have a sentimental history. “Pull together some seasonal favorites, guilty pleasures, or snacks that bring back great memories,” says Van Son. “Did you attend an epic game together? Create a ballpark-themed snack box with popcorn, beer, soda, and boxes of candy.”

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Send Them Off in Style

Whether you’re asking your groomsman to join you for an exotic destination ceremony, a cross-country bachelor party, or a weekend at your family’s mountain cabin, send them off in style with a leather weekender bag. (It’s a versatile, grown-up version of that tired duffel he’s been traveling with since he showed up in your freshman-year dorm room.)

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Gift a "Dopp Kit"

A good-looking Dopp kit will store his toiletries for a business trip, long weekend, or pre-wedding travel. Fill it with must-have grooming products for the big day, like a high-end razor, travel toothbrush, and nail trimming set, to make sure he’s photo-ready.

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Send a Handwritten Note

Reach out to long-distance friends—and your local go-tos—with a handwritten note asking them to join your wedding party. Keeping this letter short and sweet is completely acceptable; share a few favorite memories, thank him for his friendship, and ask him to stand up by your side.

groom sitting down while his groomsmen touch his shoulder — Photo by Elias Kordelakos

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Consider Gifting Skincare Products

High-end skin care products, beard oils, face masks, and hair care items are small luxuries he might not splurge on for himself. But, for the friend who’s always taken care of you, they’re a subtle way to say thanks.

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Buy a Set of Cufflinks

A set of cufflinks is a classic groomsman gift. If you’re planning a black tie wedding, choose a formal, monogrammed set that he can wear with his tuxedo; otherwise, look for a shape, color, or symbol unique to each man’s personality that he can wear to future events. (For groomswomen, choose a necklace, bracelet, or earrings.)

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Gift a Pair of Socks

Help your groomsmen put their best foot forward with fun, festive socks. While many grooms give socks for their men to wear at the wedding, that’s not required; pick the colors of his favorite soccer team, your alma mater’s famous hues, a bold print, or a custom pair with "make-him-laugh" photos of the two of you.

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Provide Practical Wardrobe Pieces

The most practical gifts you can give your wedding attendants are the specific wardrobe pieces they’ll need to wear for your ceremony and reception. If you have your aesthetic finalized, then a patterned pocket square, specific bow tie, or embroidered suspenders can do double duty as both an invitation to join the wedding party and a day-of accessory. (Offering to pay for his suit or tuxedo, if that’s within your budget, is often a welcome gesture, too.)

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Create a Custom Bottle

Raise a glass to your long, happy friendship—and the years you have ahead—with his favorite beverage in a custom bottle. Whether it’s a six-pack, a bottle of bourbon, or a perfectly aged wine, a personalized label turns any drink into a celebratory moment.

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Pay Homage to Your Favorite Video Game

Pay homage to years of afternoons spent gaming with a wedding party invitation designed to mimic iconic video games, like Fortnite, Call of Duty, or Minecraft. Inside each box, a note reads, “Error: One of your party members lost their single status. Join their wedding party as a groomsman to continue.”

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Create Custom Golf Balls

A golf outing—whether with one potential groomsman or the entire party—gets a personalized finishing touch with custom golf balls. Have a set created for each of the men, or choose a golf-related pun (like, “Are you ready to PAR-TEE as one of my groomsmen?”) and hand them out all at once.

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Honor Your Favorite City

Pair a personalized bottle with a set of glassware inspired by a favorite city: Where you grew up, where you first worked together, where you went to college, or where you and your partner are tying the knot.

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Share a Roast

For the friend who’s always bragging about his beans, a gift box of coffee is a nod to his search for the perfect roast. If he’s from out-of-town, add a pound made by a local roaster; a thermal travel mug lets him keep his energy up with all-day drinking.

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Wrap Up a Bottle of Cologne

If you know his favorite cologne, wrapping up a new bottle of his signature scent is a thoughtful and useful gift. (And if his signature scent is more, “I slept in these clothes,” then this is the perfect time to gift him a new fragrance he can make his own.)

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Plan a Barber Shop Visit

While your fiance sets up a spa day for her potential bridesmaids, plan a trip to a men’s barber shop to treat the men to a professional shave. (If it’s too hard to schedule this as a groomsman-invitation activity, let them know it’s in the works for the wedding morning.)

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Gift Them a Watch

Make sure your chronically late groomsman gets to the church on time—and gets you there, too—with a sleek and stylish wristwatch. Opt for a modern, wood-band version; a classic leather strap; or the newest smartwatch for your tech bro buddies.

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Buy a Small Deskside Tray

A tidy dresser starts with a chic catchall tray to corral loose change, chargers, cufflinks, and collar stays. No matter how much he collects in a leather, concrete, or wooden tray, his space will look cool—not cluttered.

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Put Together a Picture Frame

Gift your groomsmen a sophisticated marble, wooden, or metal frame with a recent snapshot of you both together. Or make it even more special by finding an old photo of you with each man to present in the frame when you invite him to join your wedding party: You with your baby brother on the way he came home from the hospital, with your lifelong best friend in the canoes at summer camp, or with your fraternity brothers at graduation.

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Honor the Moment With a Personalized Notebook

Give your best man (or any of your groomsmen) an elegant, initial-embossed notebook, perfect for jotting down bachelor party ideas and jokes for his speech while mapping out work projects and recording minutes during volunteer meetings.

Here Are the Top Groomsmen Attire Questions, Answered