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Article: 37 Ways to Ask “Will You Be My Groomsman?”

37 Ways to Ask “Will You Be My Groomsman?”

Will You Be My Groomsman

Wondering how to ask groomsmen to be in your wedding in a unique and awesome way? We know that it can be tough to figure out the best way to ask that important question. When you ask “Will you be my groomsmen?” you want to show your closest friends how important they are to you with one awesome, unique gift.

Oftentimes, groomsmen's gifts are also items that your guys can use before, during, or after the wedding. When you use any of these fantastic gifts or groomsmen gift boxes to ask your best friends to be your groomsmen, there’s no way they will say, “No!” Now let's take a look at some of the most amazing gifts you can get when asking a groomsman to help you on your way to your next exciting journey!

1. Take a Drink . . . or Two

Set of 5 Blackout Flasks for Groomsmen

One of the best ways to ask someone to be in your wedding party is to give them a gift that they can use leading up to, during, and after the wedding. This set of black flasks are the perfect gifts because they’ll fit snugly in your groomsmen's pockets and blend in flawlessly with their wedding day outfits. They’ll love being able to take a few drinks of their favorite liquor throughout the business of the wedding day!

2. Custom Groomsmen Gift Bamboo Mini Bluetooth Speaker

Bamboo bluetooth speaker for groomsmen
Man holding bamboo Bluetooth speaker for groomsman

Finding a way to ask him "Will you be my groomsman?" without getting too sentimental. Get him these booming Bluetooth speakers for when you ask him that important question. Made from authentic bamboo, this Bluetooth speaker is perfectly durable and has the right construction to kick a beat super hard. It's also fully personalizable, so you can get his name on it with no extra effort. Having a portable Bluetooth speaker is a necessity if he enjoys music, podcasts, or audiobooks, so don't pass on this gift.

3. Propose to Your Groomsmen With a Mini Baja Chase

Dune buggy racing through the desert
People racing dune buggies in the desert

There’s no trip like going to Vegas, especially when you’re with your best buddies. Go to Vegas and propose to your groomsmen with this awesome Baja dune buggy experience, which will have them saying "YES!" without a hitch. This package is an incredible one as it allows you to go as fast as you want on dune buggies on 15,000 acres of pure desert terrain. You guys will experience all types of exciting terrain, including dunes, gravel, hills, valleys, and more. Enough to keep your hearts racing!

4. The Gift Set that Conveys the Right Message

Custom Groomsmen Gift Crate How to Ask Groomsmen

When it comes to how to ask groomsmen to be in your wedding using gifts, the message the gift sends is more important than the gift itself. For example, this groomsmen gift box set shows your buddies that you took the time to make each box customized just for them. Throw in a small bottle of their favorite booze or a stogie or two of their favorite brand to make it even better.

Related: Cigar Gift Set

5. Manliest Groomsmen Gift Ever

Personalized Cigar Glass with Damascus Knife

Make them feel like the most badass guy to ever get invited into a wedding when you ask him to be part of your wedding party with this Damascus knife and custom cigar whiskey glass. Not only will this set be great for celebrating, but he’ll carry this knife with him for the rest of his life. Whether he needs to cut a stray string off his tux or cut a rope as he is working on the ranch, your groomsmen gift will always be there when he needs it the most.

The groom and groomsman outdoors having fun

6. The Beard Hedger Pro Luxury Grooming Kit

Beard Hedger Pro grooming kit sitting on counter
Beard Hedger Pro grooming kit laid out

Keeping those beards trimmed, cleaned, and tight can be a challenge without the right equipment. With this beard grooming kit, he'll have absolutely everything he'll ever need in one place to keep his beard tip-top. This grooming kit comes with all the necessities and more, including beard shampoo, conditioner, oil, balm, trimmer, and more. It also comes with a travel pouch so he can easily keep everything in one place in his bathroom or even take it with him when he's on the road.

7. Ask Him to Be Your Groomsman with a Gift That Rocks

Groomsmen Custom Rocks Glass

Make asking “Will you be my Groomsman,” as easy as raising a toast to one of your best friends with this custom rocks glass. Engraved with their name, title, and the date of your wedding, this is the perfect personalized gift for any groomsmen. From the bachelor party to the reception, they’re sure to get their use out of this awesome gift. Even years later when the two of you are hanging out, you can be sure he will still be having his Whiskey Sour, Old Fashioned, or whiskey on the rocks from this fantastic glass.!

8. 13 Piece Ultimate Boxed Beer Groomsman Gift Set

Beer box groomsman gift set with snacks

You want to go all out when asking your groomsmen to help you on your next big adventure, so you've got to get them a big badass gift. This beer gift set is just what the doctor ordered with a ton of awesome gifts that he'll be sure to love. This box set comes with four pint glasses, a bottle opener, and a bunch of bar snacks with bowls, so he'll be able to entertain you and your buddies the next time you hang out. It also comes with a convenient box that fits everything inside it, making this set incredibly fun and functional.

9. Viking Horn Mug Gift Set with Custom Box

Viking horn beer mug gift set with bottle opener and gift box
Viking horn beer mug standing alone

Not sure how to pop the question to your groomsmen, but you know you want to wow them? Get them this iconic Viking mug gift set, which comes with some pretty cool gifts that'll make them hop on board in a second. With a gift set containing several items, including a badass Viking horn, a bottle opener, and a wooden box to keep everything in, they'll have everything they'll need for a good time. On top of that, you can get them personalized, so you'll be giving them more than a gift.

10. How to Ask a Groomsman? With a Decanter, of Course!

Custom Decanter is How to Ask a Groomsman

What better way to ask one of your best friends in the world, “Will you be my groomsman?” than with their own custom decanter. After all, you know there are going to be a few drinks going around at your bachelor party, and this gift not only gives them a sweet piece of glassware, but a memorable keepsake they can enjoy for years to come. Who knows, they may even pour you a drink from this memorable gift a few years later when the two of you are still kicking it!

11. The Classy Groomsmen Gift

Engraved Set of Five Groomsmen Pint Glass Set

The men you want in your future wedding party are classy gentlemen, so you want to give them a classy gift when you ask them to be your groomsmen. They’ll definitely want to toast to you and enjoy a cigar immediately upon receiving this pint glass and cigar gift. You and your boys will have a blast together enjoying your favorite beer and stogies.

12. Custom Straight Razor Kit with Replacement Blades

Custom straight razor kit for groomsmen
Man shaving his neck with a personalized straight razor

Getting your groomsman a straight awesome gift can set the perfect tone when asking him to be your groomsman. With this straight razor kit, you'll have done just that and more. This kit is incredible as it comes with a high-quality single blade razor, a travel pouch, and five replacement blades. These blades are made from high-quality stainless steel, so they'll have the sharpness and longevity to keep your groomsman's face smooth for a long time.

13. Fossil Leather Magnetic Multicard Wallet

Fossil leather magnetic wallet

It's hard to beat a groomsman gift that's made out of high-end leather. With this Fossil leather wallet, you'll be giving him a gift that will not only be used every single day but a gift that's incredibly stylish. This leather wallet is compact and perfectly designed to keep just what he needs close by and safe. With its magnet strap, he can keep his cash close and right next to his credit cards when he needs them. The best part, he won't have a bulge coming from his back pocket when he sits down. These types of wallets are the best!

14. When You Know It's a Big Ask

Custom Colossal Mug for Groomsmen

Struggling on figuring out just how to ask a groomsman to be part of your wedding? If you’re nervous at all, simply go BIG! This huge beer mug is a great gift for all of your groomsmen, they can easily toast you and enjoy a brewski at the bachelor party or reception from their custom mug. However, what makes it even better is that it holds a liter of beer, which is up to 3x more than a traditional beer mug. How cool of a groomsmen gift is that?

Related: Custom Beer Mugs

15. Hatchet and 50 Cal Ammo Can Ask a Groomsman Set

Hatchet and ammo can groomsman set
Ammo can groomsman gift set sitting out in nature

Not entirely sure what to get the groomsman you're about to ask? Even if you've known him for years, giving him a badass ammo can gift set is a great way to ask "Will you be my groomsman." This isn't just an ammo can, it's a gift box that contains some awesome groomsman gifts, including a flask, beer glass, and hatchet. The best part is everything is personalizable, including the ammo box, so it'll be something he can cherish for years to come.

16. Hayden Mens Toiletry Bag with Straight Razor Shaving Kit

Dopp kit for asking a groomsman

Does he go to the gym or travel a lot? It's not uncommon to have your toiletry items scattered around your gym bag or luggage, so get him this killer dopp kit. This toiletry bag is perfectly designed to hold everything he'll need when popping into the locker room or the bathroom. It even comes with a straight razor kit he can use to get the closest shave possible. It's also made from high-quality leather, which means this gift is going to last him a very long time.

Four groomsman and groom posing near brick wall

17. Serrated Personalized Knife Gift for Groomsmen

Serrated knife gift for groomsmen

Giving him the right tool for the right job is always appreciated, especially when figuring out how to ask a groomsman. This set of personalized pocket knives are incredibly thoughtful and badass gifts, especially for all your groomsmen. This pocket knife is not only personalizable, but it comes with a serrated blade, a seatbelt cutter, and a glass breaker, so he'll be ready for anything when the time comes. This is truly a classic and thoughtful gift any groomsman would love.

18. A Custom Whiskey Stone Set

Engraved Twist Glass and Whiskey Stone Gift Set
Man in suit drinking whiskey from a twist whiskey glass

Put a new twist on traditional groomsmen gifts with this engraved twist glass and whiskey stone gift set. You can be sure beyond the shadow of a doubt that your groomsmen will be toasting to your happy marriage all night long as soon as they open these custom gifts. Just include some booze at the party or a few mini bottles in their gift sets so they can put this set to good use right away!


19. Engraved 50 Caliber Ammo Can to Ask Your Groomsmen

Best man engraved ammo can gift box

Sometimes it seems that we have so many things lying around, that it's hard to know where to put them. With this personalized ammo can, you'll be able to ask your groomsmen the important question while giving them something incredibly useful. This ammo can is awesome as it's made from a refurbished U.S. military ammo can, so you know it's good and durable. On top of that, it's personalizable with a cool design, his name, and a date. This is a perfect gift for your groomsman that they'll be able to use for years.

20. The Ultimate Outdoor Chair by Parkit

Man standing on the beach next to outdoor chair
Voyager, The Ultimate Outdoor Chair by Parkit

What do camping trips and tailgates have in common? Chilling with your friends with some good old fashion lawn chairs. If that sounds like you guys, you've got to get them this ultimate outdoor chair made specifically for those eventful events. Designed to maximize your comfort, this chair is fully equipped with a cooler underneath the seat, a versatile cupholder, and much more. It's also made of extremely durable materials, making it a common piece of equipment that will last years into the future.

21. It’s Time to Be Your Groomsmen

Wooden Ebony Watch

This attractive ebony watch is a fantastic groomsmen gift that will make them immediately agree to be in your wedding party. They’ll love sporting these handsome, durable watches on your big day and every day after that!

22. Personalized Cigar Holder with Stainless Steel Cigar Cutter

Personalized Cigar Holder with Stainless Steel Cigar Cutter

Handing out cigars to your buddies is one thing, but where are they going to store them? That's exactly where this cigar holder comes in handy, which is a great gift that they can use more than a single cigar. This holder is ideal as a gift for your cigar loving buddies as it comes with an attachable stainless steel cigar cutter and is made of high-quality black leather. You can also get it personalized, so each member of your wedding party will know who’s belongs to whom.

Related: Cigar Accessories

23. How To Ask a Groomsman? With a Memorable Gift!

Ask Will You Be My Groomsman with Engraved Shadow Box

When you bring someone into your wedding, you’re not just creating memories for yourself, you are also including your best friends on some of their favorite memories ever. Ask them, “Will you be my groomsman,” with a gift that lets them hold onto those memories forever, an engraved shadow box! Inside, they can start their collection of cigar bands, beer caps, movie tickets, or anything important to you and their friendship.

24. Ask Groomsmen with Manly Mugs

Will You Be My Groomsmen Beer Mug Set
Two beer mugs full of beer in front of bar snacks

Groomsmen embody some of the manliest qualities during their time being your best men, so make sure you get them an equally manly gift with this personalized beer mug box set which comes with not just one but two beer mugs! Nothing will feel manlier than toast after toast to you from these gorgeous beer mugs while you and your groomsmen have some of the best and most memorable times in your lives.

25. Unique “Will You Be My Groomsman?” Gift

Engraved Bamboo BBQ Tools Set

This set of bamboo tools are a fantastic keepsake gift for your future groomsmen. With the personalization on the box, they’ll remember your wedding vividly every time they see it. Also, with the fantastic grilling tools, they’ll feel more confident in their barbecuing skills, which means tons of super fun backyard barbecues from here on out.

26. Engraved Whiskey Stone Gift Set with Buckman Glasses

Engraved Whiskey Stone Gift Set with Buckman Glasses

Keeping your whiskey chill without diluting it with water is important to get a full body taste of your favorite whiskey. Make sure your groomsmen can have that same exact experience with this whiskey stone gift set. This gift set comes with two Buckman style whiskey glasses, a set of whiskey stones, tongs, and a custom engraved wood box to keep the stones and tongs inside. The best part is it's all personalizable, so they'll have a keepsake they can use on the regular.

27. Watch You Tie the Knot

Two ties inside fancy tie travel case

Wondering how to ask groomsmen to be in your wedding who hate dressing up? It’s simple: give them a tie they actually want to put on! This tie gift set will have them begging to try on their suit as soon as possible. They’ll love the way they look in these ties, and they’ll love seeing the matching ties in your wedding photographs that they'll have for the rest of their lives. On top of that, it comes with a nifty tie case. It will mean so much to them that you found an attractive tie set that everyone loves.

28. Groomsman Personalized Beer Mugs and Bottle Openers

Custom Beer Mug Groomsmen Sets

Get your groomsman a badass gift that they'll be able to use right away at your wedding. With this set of groomsman gifts, you'll have done just that and more. This set is amazing as it comes with a personalized beer glass, a custom pocket knife, and a bullet bottle opener. It also comes with a cool bowtie, so you can all have a good laugh while enjoying your favorite beers together before you walk down the aisle. Can't get much better than this!

Four groomsmen throwing groom into the air

29. Personalized Set of 5 Survival Groomsmen Knives

Personalized survival groomsmen knives
Zoom in on personalized tactical knife set items

You never know when you're going to need a knife and other gear, but you'll be happy that you have it when you need it. Get your groomsmen these sleek personalized tactical survival knives, which come in a set of five and can be added to. These knives are incredible with a 4.25 inch blade made of hardcore carbon steel with two types of serrated edges. On top of that, it comes with a secret compartment that includes a compass, sewing kit, fishing set, and some matches. Can't be too prepared, and this will help your groomsmen be sure of that.

30. Engraved Marble Cigar Ashtray

Personalized marble cigar ashtray with unlit cigar

Instead of ashing your cigar in a beer can or bottle, consider doing it in a proper receptacle. With this personalized marble ashtray, you'll have exactly what you'll need to keep your cigar ash in one place. As far as groomsmen gifts are concerned, this is perfect for when you guys are lighting up before or after the wedding ceremony. It holds four full size cigars and has plenty of space to spare for all the ash you guys will be putting down.

31. Phenomenal Personalized Flask Set

Embossed Flask Box Set for Groomsmen

Ensure that no matter where you and your groomsmen go, that they can always have a toast or quench their thirst with this embossed flask gift set. What better way is there to ask them to be one of your groomsmen than with a classy gift that they can use at the bachelor party and have on their person at the wedding and reception?

Related: Custom Flasks

32. How to Ask Groomsmen in a High-Caliber Way

How to Ask Groomsmen with Custom 50 Cal Bottle Openers
Groomsman opening beer bottle with bullet bottle opener

Ask your closest friends to be your groomsmen with these super unique bullet bottle openers. They’ll think these real 50-caliber bullets with their names on them are insanely cool, and they’ll love that you took the time to find a gift as novel and useful as these bottle openers.


33. Shinola Detroit Belt Gift Set for Groomsmen

Shinola Detroit Belt Gift Set for Groomsmen

Being a part of a wedding party usually means spending money on your own outfit. If you want to help them out a bit, get them this awesome belt gift set, which will certainly not go unnoticed by your groomsmen. With this gift set, you can choose between two different leather straps and two different belt buckles by simply attaching the distinct pieces together to create four unique belts. For whatever attire you plan on wearing, there's a belt combination that will fit your style.

34. The Coolest Ammo Can Gift Set for Asking Groomsmen

Set of 5 Ammo Can Gift Sets for Groomsmen

Ask, “Will you be my groomsman?” to your closest friends with an extremely impressive ammo can gift set. These ammo can gift sets will absolutely stun them because of how amazing they are, and your friends will know how much they mean to you. With their new glasses, they’ll give a toast to you, and they’ll store mementos from your wedding inside the ammo can.

35. Personalized 9 Inch Hatchet for Best Man Gifts

Personalized 9 Inch Hatchet for Groomsman Gifts

If you're going for the classics, you've got to do it right. This personalized hatchet hits the mark on that exact point and will be something he'll be talking about for years. This hatchet is not only badass looking, but it's actually incredibly practical due to its high-quality construction and materials. It's even personalizable, so you can put his name, a message, and a date right on the 9 inch blade. This pre-sharpened hatchet comes with a protective sheath and many years of good times.

36. Engraved Wood Groomsman Watches with Leather Bands

Five groomsmen watches with leather bands

Keeping it classy isn't always easy, especially when you're looking for gifts for your groomsmen. This set of engraved wood watches keeps you and your groomsmen ultra classy since they're some of the most uniquely styled watches out there. These watches are stunning due to their construction of durable and stylish wooden material. They're also personalizable on the back, so there's no way they'll mistake their watch for another groomsman. This is a remarkable groomsman gift they'll be sure to love.

37. Proper English Custom Pub Sign for Your Groomsmen

Proper English personalized sign

Do you guys have a designated drinking zone at each other's places? If so, you've got to get them this awesome custom pub sign, which is a great gift for guys with a man cave or home bar. Made with high-quality, dense wood, this sign is made to last. Easily turn any space into a proper English pub that will bring attention to the task at hand; enjoying a nice drink with friends. You can also get three lines of text and a date etched onto it, giving it a unique personal touch.

How To Ask Groomsmen FAQ

How do you ask someone to be a groomsman?

Keep it casual and throw in a joke if you want. The thing is you’ve probably known your groomsman for a long time and it’s likely you know his style of communication. Light and fun are what it’s about, and throwing in a gift doesn’t hurt either.

Should I get a card when asking my groomsman?

Yes! It doesn’t have to be some fancy Hallmark card, but you should get something that goes along with the gift you get him when you pop the question. Keep it short and simple. You want the message to come across through your gift more than anything else, so the card is just a cherry on top.

Is it rude to say no to being a groomsman?

It’s not rude and don’t take it personally. Some people aren’t able to handle the responsibility and pressure that ensues when they’ve been tapped for the role of groomsman. But if you make a compelling case upfront with an awesome groomsman gift, the answer will more than likely be yes, so get him a badass gift.


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