How to Ask Your Friends to Be Groomsmen in Your Wedding

Groomsmen have a lot on their list in order to support the groom: renting suits or tuxes, attending wedding events, writing a speech, getting along with everyone in the bridal party. Finding a clever way to ask them to be in your wedding will show your appreciation from the get-go.

First Things First – Etiquette

Pump the Brakes: If you’re having a long engagement, don’t worry about securing your groomsmen right away. Friendships may shift over time and you don’t want to be caught in a sticky situation of having to backtrack on your offer. Plan to ask everyone eight months to one year in advance.

Choose Wisely: You may be stoked about a new friend, but it’s better to play it safe by choosing groomsmen who have been in your life for a long time. In the space between wedding planning and the wedding day, your budding friendship could go in one of many uncertain directions.

Tune Out Obligation: Even if you were in someone else’s wedding party, you’re not obligated to ask them to be in yours. Every wedding is different. You may have a huge family who fills in all the groomsmen slots or you may be going for an understated, small bridal party. The point is to be happy with your choices before, on and even after the wedding day. Those pictures will last forever!

Disregard Gender: Your Best Man can be your sister; your groomsman can be the female cousin you grew up with. There are no rules. Choose the most important people in your life, regardless of their gender.

Be Just a Little Bit Formal: You don’t have to make a huge event out of talking with your future groomsmen, but don’t take an entirely casual approach, either. Instead of emailing or texting them, make a point to call them or speak with them in person.

Creative Ideas for “Proposing” to Your Groomsmen

Build a Groomsman Starter Pack: Clue them into the fact that you’re about to ask them to be a groomsman by gifting them with a wedding day starter pack. Include things like a shaving kit, cufflinks, tie bar and socks.

Create a Groomsman Box: Unlike a starter pack, the groomsman’s box doesn’t have to have wedding-specific items. Start with a cool tin or wooden box, then fill it with items they’ll love, like a small bottle of their favorite liquor, an expensive cigar and an engraved lighter. Having a hard time finding a box? Search for tin lunch boxes.

Plan a Guys Day: Ask everyone over to watch the game or have dinner, then hand out “Will you be my groomsman?” cards. If you’re going to attach something small to the front, like a shot glass, use heavy card stock that won’t bend. You can also pop the question on an item they’ll be using that evening, like coasters or napkins. If some of the guys haven’t met yet, this is a great opportunity to break the ice.

Inject Some Humor: Weddings are serious endeavors but you can still remain lighthearted when asking your pals to join you at the altar. Instead of writing, “Will you be my groomsman?” replace it with with something more clever like, “She said ‘yes,’ now it’s your turn” or “Your service as a groomsman is required.” Leave space for them to sign their name on the bottom of the card as an “official” commitment.

Say It With a Bottle: Get a full-sized bottle of their favorite booze and attach a funny or sentimental note to the front asking them to be your groomsman. You can also have a custom label made for the bottle or have the bottle engraved. If any of your groomsman are underage, use root beer.

Send Flowers: Want to completely embarrass your friends at work? Send them a bouquet of roses with a note that asks them to “yes” to being a groomsman.

Sign Them Up for a Subscription: Even if one of your groomsmen doesn’t live close enough to come over for the day, you can still find a special way to include him. Think about his favorite things – does he love candy from his childhood, Japanese snacks, cinema memorabilia? Sign him up for a subscription box. Most services will let you send between one and three boxes, often for a lower price if this is your first time ordering. Include a personalized note asking him to be your groomsman.

Remember, it’s always a good idea to compare bridal party notes with your significant other beforehand. First, you’ll want to agree on the total number of people in the bridal party. Second, while you may not necessarily veto one another’s choices, communicating does give you the opportunity to work out any differences before the bridal party is set in stone.

by Lindsay Pietroluongo