The 24 Best Groomsmen Proposal Gifts to Help You Ask Your Guys


You (or your partner) already popped the question once. Now, it’s time to plan amazing groomsmen proposals that’ll set you up for the journey ahead. Choosing who will take part in your wedding is a big deal, so make sure you take some time to decide exactly who you want by your side. After that, you’re free to start drafting your team. 

Not sure exactly how to ask your groomsmen to be in your wedding? There are so many clever and creative ways to propose to your wedding party, whether it’s your best man, best woman, groomsmen, or groomsmaids. Make the moment count with a token of appreciation for everything they’ve done for you in the past (and the groomsmen duties they’re about to take on). 

To help you get started, we’re sharing our expert advice below, plus editor-approved gift ideas for everyone on your list. From the style gurus to the football fanatics, these presents are total crowd-pleasers.

Do You Have to Give Proposal Gifts to Your Groomsmen?

When it comes to giving proposal gifts, the first thing to keep in mind is that they’re not compulsory. Many to-be-weds choose to buy groomsmen or bridesmaid proposal gifts because they’re a sweet way to honor relationships and say “thank you” in advance. But, not buying a proposal present isn’t going to stop your loved ones from standing by your side on your big day (or persuade them to accept the role if they really can’t commit to it). Just make sure that you do thank your crew for all of their support at some point before or after the wedding.

How to Give Groomsmen Proposal Gifts

There are a few things to consider when giving proposal gifts to your future groomsmen/women and best person. For starters, do you want to ask everyone at once? Or would you rather have a meaningful one-on-one moment with each of your loved ones? Do you plan on toasting everyone’s new wedding party status afterward? Or would you prefer a chill day out fishing or playing golf? Choosing the right time and place will help set the tone for handing over your gifts and asking that all-important question. 

Lastly, think about how you want the moment to play out with your chosen friends and family. Some grooms opt for a light-hearted approach with a funny proposal card, while others prefer to take it a little more seriously. However you decide to deliver your gift, make sure it’s something personal or practical your loved ones will really appreciate—it’s not every day you ask someone to help you tie the knot!

The Best Groomsmen and Best Man Proposal Gifts

Ready to fill your cart with awesome presents? We’ve rounded up all of our favorite picks below. Not only that, but we also came up with some cool ways to ask your groomsmen and best man inspired by each gift idea. Happy shopping!

Sleek can coolers

No matter their drink of choice, they’ll appreciate the ability to keep it cool. Enter: custom groomsmen koozies. These stainless steel ones look pretty slick (and they’re easily reusable). They fit standard 12-ounce cans or bottles. 

Travel poker sets

Need a groomsmen proposal gift for the gamer in your life? Honor his interests with the game gentlemen have been playing for decades: poker. This weather-proof poker set is specifically designed for playing on the go and outdoors. It includes 52 playing cards, 120 metal poker chips, and the instructions for Texas Hold’em. 

Cameo video messages

Cameo is an amazing best man proposal idea, especially if your favorite guy doesn’t live nearby. The site plays host to A-listers (and B-listers and C-listers) from various facets of the entertainment industry, including athletes, musicians, actors, reality stars, and more. Simply choose a celeb and request a personalized video message. 

Personalized golf balls

If you spend every Sunday hitting the fairway, a golf-themed groomsmen proposal gift is a nice way to tee up your friendship. These personalized golf balls can be stamped with each person’s name for an elevated twist to their usual gear. (Bonus: They’ll no longer argue over who owns which ball.)

Engraved wooden watches

Let your guys know it’s time with a sleek wooden watch engraved with each person’s initials, new wedding title, and the date of the big day. This unique accessory is made from authentic sandalwood and high-quality stainless steel. (And hopefully it’ll keep them on track with their duties, like planning an epic bachelor party.)

Custom coffee mugs

Your squad will love seeing their mugs on these novelty coffee mugs. This playful gift idea makes the question “Will you be my groomsman?” crystal clear. Simply send the Etsy seller a photo of each person you want a caricature of and they’ll take it from there. For an extra-personal touch, include a bag of gourmet coffee (or as we like to call it: wedding planning fuel). 

Wedding title baseballs

The perfect way to ask a baseball fan to be in your wedding? With an actual baseball, of course! Each ball is customized with your friend’s new wedding title. When placed inside the gift box, the message reads: “Take a swing at being my groomsman.”

Insulated travel tumblers

Everyone needs a sturdy, insulated travel tumbler, whether it’s for drinking coffee while commuting to work or sipping beer around a campfire. Corkcicle has a selection of stylish travel tumblers for everyone in your group. The best part: Items from the site’s wedding party collection can be personalized with your crew’s names. 

Etched windproof lighters

Don’t be afraid to get creative with gifts for asking your groomsmen. These useful lighters are personalized with each person’s first name and wedding role. Plus, they come in four sleek colorways. 

Cool drinking gadgets

If a personalized bottle opener feels overdone to you, skip it and go straight for this way-cooler gadget. Your groomsmen will be seriously excited to try out this bad boy. It conveniently cuts off the top of a standard beer or soda can, transforming it into a smooth-rimmed drinking cup. Adding a shot of liquor or slice of lime has never been so easy.

Personalized baseball bats

Here’s another creative gift idea for baseball fans. This Little League-approved Rawlings bat is crafted from ash wood and personalized with your friend’s name, role in the wedding, and the date. It’s especially thoughtful if you’ve spent time on the field or in the stands together.

Scented groomswoman candles

There’s no reason your groom’s crew can’t include your favorite lady. This lovely scented candle will make for a charming groomsmaid proposal gift. The label is printed with a sweet explanation of what makes a groomswoman, including the final definition: “you.” 

Personalized hip flasks

Throw it back to your college drinking days and present them with a sophisticated flask featuring their monogram and hard-earned wedding title. It’s one of the best groomsmen proposal gifts for your old college roommate or go-to drinking buddy. 

Handcrafted cuff links

A shiny new pair of cuff links will add a dapper finishing touch to their wedding attire. These handmade leather and stainless steel accessories are stamped with each person’s initials for a truly one-of-a-kind look. 

Groomsmen proposal socks

Small tokens are all you really need to get your crew on board. These groomsmen proposal socks say it all for you with the words: “Will you stand as my groomsman?” There are 12 different hues to choose from. If you’re not sure which they’d prefer, you can’t go wrong with classic black.

Custom fish hooks

Nothing says “be my groomsman” quite like a gift engraved with the wedding title. This cool fishing lure is personalized with the word “groomsman” and the date on the front, and there’s space to add your own personal message on the back.

Fancy tie sets

Propose to your crew with some chic accessories that’ll serve them well at the pre- and post-wedding festivities to come. This tie and pocket square set is the perfect proposal box for style-savvy groomsmen. If they’ll be donning a tuxedo at any point, go for the bow tie gift set instead.

Monogrammed humidors

If anyone in your crew is big into cigars, they’ll fully appreciate an elegant humidor with their name, monogram, and the date of your nuptials. You can give your loved one the humidor on its own or make it a box set with an engraved lighter and ashtray.

Stemless wine glasses

If you’ve often bonded over a crisp glass of wine, treat your future groomsman or groomsmaid to a set of stemless red wine tumblers engraved with their name or monogram. There are six different designs to choose from, so you’re bound to find one that suits their style. 

Personalized footballs

Do you and your crew always reunite during Super Bowl season? Or maybe you used to play together back in high school or college? Whatever the reason for your connection to the sport, a personalized football is a lovely way to honor your unique friendship.

Superhero beer mugs

Have you ever seen a cooler beer mug? Inspired by a traditional German stein, it’ll seriously elevate their usual pint. If the carved wood exterior isn’t enough to grab your attention, you can also add an engraved plaque featuring their name, title, logo of their favorite superhero, and the wedding date. It’s a great groomsmen gift idea they’ll hold onto as a keepsake long after you say “I do.” 

Luxe dopp kits

Some of the best gifts hint at the festivities to come. If they’ll have to travel for the wedding (or an awesome bachelor’s weekend), these classic leather toiletry bags will be a welcome present. Have each one personalized with your crew’s names so they don’t get mixed up.

Junior groomsmen tumblers

These mini personalized tumblers come in 11 different hues, so you can select the one that your junior groomsman loves the most. Simply let the Etsy seller know the name and title you’d like to include and they’ll get to work creating a useful, personalized gift. 

Humorous proposal cards

If you’re not usually the sentimental type, let them know a formal groomsmen proposal was all your fiancé’s doing with this funny groomsmen proposal card that reads “Will you be my groomsman?” or “Will you be my best man?” inside.


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