How To Ask Groomsmen: Try These 9 Great Gift Ideas

Choosing the Perfect Groomsmen Proposal Gifts

Groomsmen Proposal Gifts

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While most people think of groomsmen gifts as something that you give out at the rehearsal dinner or reception, offering “groomsmen proposal gifts” is the perfect way to formalize the process of asking your best friends and family members to be part of your wedding.

Making sure everything will fall into place on your wedding day depends a lot on the type of friends you choose to stand by your side. Selecting the right groomsmen is essential in order to have a successful wedding. 

Now don’t laugh — “proposing” to your groomsmen is a thing these days, and you definitely don’t want to overlook the details of how to ask groomsmen to be part of your wedding.

After you’ve mentally chosen the right guys following the steps that we cover below (as well as here) and that The Knot covers here, you want to make sure you get a resounding “yes” from your newly minted groomsmen.

First, Think About Who To Ask To Be Your Groomsmen

You have friends from school, family, work, the military, sports, and your future wife’s family and friends to select from. Determining who you want to ask to be your groomsmen is an important decision that might take a bit of thought.  

Choose friends who are reliable. This isn’t the day for the friend who tends not to show up on time or who you don’t feel will take the day seriously. If you feel someone might get their feelings hurt, consider making them an honorary groomsman in title, but who doesn’t have many responsibilities.

Choose groomsmen who are happy for you. You might have a friend or two who aren’t too keen on you getting hitched in general, or hitched specifically to the woman you’ve chosen to marry.

Maybe they want to keep you in their circle of bachelor friends or they try to get you to postpone your date. You don’t want or need any negativity so, again, maybe these friends get an honorable mention.

Then, Pick Out Your Groomsmen Gifts

Once you have your list of groomsmen, it’s time to determine your groomsmen proposal gifts. The good news here is that you don’t need to look for gifts that are specific to a “groomsman proposal” — you can simply shop from any website or store that offers personalized gifts for men.

The only difference here is that you may want to modify the customization slightly to reflect the fact that you are asking them to be in your wedding party, rather than going ahead and putting name, “Groomsman,” and wedding date on there.

Groomsmen proposal gifts -- custom flask

These can be the same for all of your friends, or you can select individual gifts for each. It completely depends on your friends and their interests. Check out these trendy ideas and choose what works for you.

And don’t forget about asking someone to officiate your wedding. This blog post has some great ideas for handling that situation.

Groomsmen Proposal Gifts

Personalized .50 Caliber Bullet Bottle Openers

Black Matte Bottle Opener

Here’s a gift that is simple for giving to your entire team, because everyone always needs a bottle opener. Especially when you have a crew of rugged, tough friends, these military-grade, spent ammunition .50 caliber bullet bottle openers are perfect. Available in matte black, silver, and classic brass so you can pick one that fits your wedding colors or personal preferences.

Each bottle opener is made in the USA and you can customize each one with up to three lines of words, initials, numbers, or a phrase. Kick it up a notch for a more formal wedding or for your best man by getting personalized gift boxes. Let your friends know you’d “take a bullet” for them, and you’ll be certain to get a good response.

Score Big with the Sports Fan Groomsmen

You can literally score big by taking your groomsmen out to the old ball game. Score Big also has you covered if sports aren’t your thing or that of your groomsmen. Use the website and save money on concerts, comedy shows, and theater as well as sports. 

There are some other really cool sports-related gifts if you don’t live in a city with a collegiate or professional team. Give your groomsmen a game ball from Big Game Football or a customized Louisville Slugger to commemorate asking them to be part of your wedding. 

Grooming Kit

The better you look the better you feel. And you will want your groomsmen looking and feeling good for your wedding. Why not give them something from The Bearded Bastard or Bearded Veterans Club?

Both sites carry a complete line of beard products. They’ve also got soaps, shaving oil and razors, face and skin care, and hair products.

You’ll find something for each of your groomsmen whether they look like Grizzly Adams or James Bond.

Necktie Set with Cufflinks

Whiskey Barrel Cufflinks

Regardless of the number of ties your groomsmen may already have, it’s rare to go wrong here, especially if you are looking for a unique design. Consider adding their monogram for a bit of personality. You could also choose a tie and cufflinks that your groomsmen would actually wear for your wedding.

This works well if your ties are especially fun or follow a certain theme. Create your own set by pairing your tie with these .50 caliber bullet cufflinks that add a bit of power and attitude to any outfit. Or try the whiskey barrel cufflinks made from authentic Tennessee whiskey barrels. 

Ammo Box Sets

Ammo Can Survival Kit

For the guys in your life who have been in the field with you, have your back at every turn, and appreciate a bit of gun decor, these ammo cans do the trick. These “Survival Kits” are a good way to pop the question as you need your buddies to help you “survive” the day.

Let them know you would appreciate their help with this recycled .50 caliber matte black, gloss red, or authentic OD green ammo can. The set also includes two pint glasses, stainless steel flask, a funnel, and a .50 caliber bullet bottle opener.

Or, you could simplify things a bit and go with a custom engraved ammo can that you then fill up with other products from our site or gifts you collect from elsewhere — beer, booze, cigars, you name it. The best part about these ammo can gifts? You don’t need to put any time into gift wrapping or labeling it. 

Pub Crawl

If your groomsmen like a good beer and are more into experiences than possessions, then a pub crawl or brewery tour may be the perfect way to celebrate their participation in your wedding.

Beer isn’t your thing? Some cities have whiskey crawls or try touring a local distillery. If you rather not give an experience but an actual gift then try the Craft Whisky Club. It’s the gift the keeps on giving all year long. 

A Fountain Pen

A fountain pen isn’t only for writing but it’s also an art piece on its own. Check out our selection of fountain pens here, which you can have custom engraved with your groomsmen’s names. These will look good on a desk at work or in a study.

Or if you’re looking for something extra fancy, you can opt for something more upscale like this Lamy Studio Fountain Pen.Fountain Pens for Groomsmen Gifts

You know how you’re always losing pens, looking around and unable to find one when you need it?

Well you’ll have the opposite problem with a nice pen like this one.

I bought this exact pen (and one in black) on a whim about 8 years ago, and I still use both of them on a daily basis. Writing with a fountain pen nib took a little getting used to, but I came to love it quickly.

These pens can handle standard refill cartridges that are available at any office supply store, or you can also use the included converter with the refillable cartridge to add more ink or change colors whenever you want.

And since I know they weren’t cheap, I’m very careful about making sure I don’t leave it behind somewhere or put it in the wash.

It’s sort of how you pay a lot closer attention to keeping track and taking care of your pair of Maui Jim sunglasses than you do with a gas station pair.

Journals and Diaries

This suggestion goes hand in hand with the fountain pen idea up above. A nice pen along with something unique to write in would be a great way to ask your closest friends to be part of your wedding.

Slip a handwritten note inside, or use the first page to write a meaningful message, and voila — the gift also acts as the groomsmen proposal itself.

You could go with something relatively simple like these notebooks from Moleskine.Groomsmen Proposal Gifts - Journals

But if I was going to buy journals for my friends I would definitely spend a few extra dollars to get something memorable like the below leather journal. You can click here or on the photo to pick one up from Amazon.

Leather Journal for Groomsmen

For the businessman or someone just looking to make a change in life, a daily planner is another good option to help him organize his life and boost his productivity.

Google Calendar and iCal are great, but there’s just something different about taking the time to hand-write your daily/weekly/monthly schedules and goals when it comes to keeping on track.

Having used one for the last 6 months or so, I’m partial to Brendan Burchard’s High Performance Planner which you can check out here.Groomsmen Gifts - Daily Planner

Aside from the aforementioned benefits of writing down your daily goals and “must-do” tasks, this planner incorporates end-of-day introspection in a meaningful way.

I know it sounds a little touchy-feely, but you’ll find significant value by reflecting each night. It helps to recap what you did well, poorly, what situations tripped you up, and how you can do a better job tomorrow — not just at work, but with your health/wellness and personal relationships as well.

Car Accessories

For those that love their cars you can give them items like car ornaments (bobbleheads, mirror dice, unique gear knobs, etc.) and car wash kits (first make sure they love washing the car themselves). For the motorcycle enthusiasts, some leather gloves or a patch for their jacket would be cool. The point is to find something that is unique and fits your groomsmen.

Go Deep with Whiskey Barrels

Deep South Whiskey Barrels and Red Head Oak Barrels have a variety of customizable products including their best-selling oak barrels which can be used for barrel-aging spirits to tweak their flavor or just as a cool way to dispense the liquor of your choice.

Their custom bar mirrors and wall hangings also make great groomsmen proposal gifts. Maybe your groomsmen would prefer a drink with a different kind of kick — if so, try the whole bean coffee from Deep South Barrels. 

Groomsmen Gifts Make a Difference

It’s important not to overlook what you get your groomsmen or just assume that they can’t wait to be your groomsmen. It’s a lot of work, money, and time to invest. Help them make the right decision with these winning groomsmen proposal gifts.

These are the people that are to stand by you before, during, and after your big day. Make sure they know they are appreciated by getting them a quality unique groomsmen gift.

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