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Groom 101

Groomsmen Proposal Guide: How to Pop the Question (Again)

Kimberly Easter groomsmen in black suits

You popped the question and she’s said yes – congrats! But have you planned your groomsmen proposal yet? What is a “groomsman proposal” you might ask? I’m sure the simple answer is glaringly obvious: a groomsman proposal is when you ask the important men (or women) in your life to be a part of your wedding party. This type of proposal has been on the rise in recent years on both sides of the aisle. Having a wedding party is a social rite of passage for both you and for the wedding party members. Your groomsmen will be both your support system and your comic relief throughout the whole planning process and the big day. Show them your appreciation by making a big deal out of their involvement!

Here’s everything you need to know about building the perfect wedding party.

Who Do You Ask to be Groomsmen?

You should choose close friends and family be in your wedding party. This is an honor that’s hard to equal, so focus on people that you have long lasting bonds with that won’t fade away over time. First, you’ll want to decide with your fiancé the size of your ideal wedding party. However, as with most wedding planning decisions, it isn’t always an easy. For most men, the question often becomes “Who should I ask?”


Without question, if you have a brother, asking him to be a part of the wedding party is a given. It’s often expected that your brother will serve as best man. If you have more than one brother, it’s also very common to have two or more Best Men.

Your Fiance’s Brother(s)

Including your fiancé’s brothers in the wedding party is also a very popular choice. It’s also widely accepted as standard practice. You’ll be joining their family on your wedding day, and asking them to be groomsmen is a great way to welcome them into yours.

Close Friends

The tough decisions start when it comes to choosing which friends to ask. It’s usually wisest to start with any life-long friends you’ve had. You can also think about close friends from high school and college. A very popular groomsman choice is the college roommate.

Remember, if you reach your maximum number of groomsmen, you can also add ushers. The number of ushers typically ranges from two to four — a ratio of one usher to every 50 guests is a good rule of thumb. But if you want to keep your wedding party small, it’s perfectly acceptable to ask your groomsmen to also usher in guests.


Cousins and nephews are also popular choices to add to your wedding party. Even if they’re young, you always the option of having a junior groomsman or usher. Other extended family members are also commonly asked to be readers, greeters or ring bearers.

When Do You Ask Your Groomsmen?

Ask your groomsmen nine to 10 months before the wedding. This gives the guys time to save the date and plan any travel that will be necessary to attend the wedding festivities.

Should I propose to my groomsmen?

If you’re feeling like “this is just another thing I have to do”, then you’re looking at it all wrong. As a guy, there isn’t as much focus on you and your wishes for the big day as their are for the bride. This is your chance to make a big deal of your wedding day on your own behalf. Celebrate your meaningful relationships by inviting those people to take part in one of the most important celebrations of your life. Asking someone to be one of your groomsmen is a sign of respect, friendship and fidelity. Why not honor those bonds with a special moment or surprise gift? It’s an invitation to the front row to the party of the year.

The Best Groomsmen Proposal Ideas

When it comes to the “How you ask”, you have nearly limitless options and possibilities. You could do something creative and funny or you could choose the heartfelt and memorable route. Your choices should reflect your personal style and the style of your relationship to the people you are asking. There are also some logistics you need to work out. Is everyone getting the same thing? Is everyone being asked at the same time? Will you ask one at a time? Once you have all the minor details, you can get to work on your surprise gift!

“Will You Be Groomsman” Proposal Box

These wooden boxes are a perfect way to ask your boys to be in your wedding party. You can have it personalized with their names and then fill it with goodies for the big day. You could add little liquor bottles, shot glasses, cufflinks, cigars, beef jerky and a million other things. You can make them all the same or tailor each box to the specific person it is being given to.

A Good Old Fashioned Beer

Let’s be honest, you just can’t go wrong with taking your future groomsman out for a drink at your favorite watering hole. If you and your buddy spend a good amount of time together hanging at a bar, it makes perfect sense to pop the question at a place that has sentimental value to your relationship.

two friends enjoying a beer together

Custom Whiskey Label

If you and your future groomsmen are whiskey-loving men, this is both appropriate and fun. The personalized labels, which sport  a “Will you be my groomsman?” message, fit onto bottles of Jack Daniels whiskey. It’s tough to imagine a better way to celebrate than with a toast and a good ole fashioned shot. To top it off, continue the whiskey theme on the big day by gifting your groomsmen mini whiskey barrels, so they can create their own custom whiskey blends using Jack Daniels, Jim Beam or their poison of choice.

jack daniels wedding whiskey labels

  photo credit – etsy

Give the Gift of Groomsmen Wedding Day Accessories

Although gifting at this stage of the game is not a necessity, it can be a nice gesture to help show your appreciation. Popping the question with Best Man, Groomsman and Usher cufflinks helps seal the deal in a classy and thoughtful way. Your pals can then wear their designated cufflinks on the big day, looking sharp and uniform.

best man cufflinks for groomsmen

“Will You Be My Groomsman?” Card

If you’re a man of few words, this mini card (or one like it) is a thoughtful and personal, yet still wonderfully simple way of popping the groomsman question. Giving a card makes the statement that having your buddy stand by your side means the world to you, while also keeping it casual and comfortable.

will you be my groomsman personal card

photo credit – etsy

A Professional Shave

An afternoon of pampering isn’t just for the ladies. Taking your future groomsmen out for a professional shave makes for a relaxing day for your soon to be “well-groomed” groomsmen. Your buddies will appreciate the gesture, and it will help get the wedding planning off to a refreshing start.

groomsman receiving a clean shave


Hobby It Up

Do you and your future groomsman have a shared hobby such as golfing, fishing or video gaming? Keeping it simple and asking your pal to be your groomsman while the two of you are on the golf course or at a baseball game is a great approach. Consider buying him a hot dog and a beer, and then pop the question upon delivery. Or perhaps ask him to be your groomsman after a day of ultimate Frisbee. Most importantly, pick an activity that represents a solid aspect of your relationship to show your future groomsman you value his friendship.

ultimate frisbee player diving for frisbee

Drinking Glasses

It’s no secret that a fair amount of drinking goes on after most weddings. Get your guys personalized drinkware for the after party. You can choose beer mugs, pint glasses, shot glasses, growlers and flasks. Choose one that fits your taste and the style of the groomsman. Have it personalized with their title and name to make a memorable keepsake for long after the hangover has worn off.

Tie One on

Does your fiance already have the type and color of tie picked out that she wants the boys to wear? Go ahead and purchase those yourself and use it as the gift your your groomsmen. Give the gift of a tie (or bow tie) and a personalized pair of cufflinks so you boys know it’s time to suit up! They have something to keep after wedding that they can use again and again.

There are ultimately many, many ways to ask your main men to become your groomsmen. Getting creative should be fun and personal. Make sure to give the idea some serious thought beforehand, so your future groomsmen know you truly appreciate their support. After all, the wedding day is also a time to celebrate the closest friendships in your life.


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