How To Ask Someone To Be Your Best Man

Don’t know how to ask someone to be your best man? Discover our top tips and advice with this complete guide.

By Deanna deBara

How To Ask Someone To Be Your Best Man
Photo by Lark & Lavendar

When you ask someone to be your best man, what you’re saying is, “You’re important to me and I want you with me throughout this entire process.” They’re the person that’s going to support you during wedding planning, throw your bachelor party, and stand next to you when you say your wedding vows.

It’s a big job—and asking someone to be your best man is a big deal. So, what exactly is the best way to do a groomsmen proposal?

Let’s take a look at a few different ways to ask someone to be your best man and, thus, your right-hand man from today until your wedding day:

Consider Whom You’re Asking (and What You Expect)

How To Ask Someone To Be Your Best Man Photo Credit // Trifonov Photography

As mentioned, being a best man is a big job. The best man is expected to participate in the entire wedding process, from attending all the pre-wedding events, to planning the bachelor party, to providing support to the soon-to-be married couple leading up to their wedding day.

It’s a big ask, and before you ask someone to be your best man, it’s important to consider whom you’re asking, what you’re expecting from them, and whether they’re the right person for the job.

For example, if you expect your best man to spend their weekends helping you choose a wedding venue, negotiate with wedding vendors, or run other wedding-related errands, you might not want to ask your best friend who just had a new baby—and doesn’t have the kind of time or energy to devote to your wedding planning as you’d want for your big day.

Or, if you 100 percent want your close friend to be your best man at your wedding ceremony, you can still ask him—you just may need to lower your expectations. For example, his new baby might keep him from running a ton of wedding-related errands with you, but he may be open to meeting for coffee once a month to go over logistics and see if there’s anything he can help with when he has spare time.

The point is, before you ask someone to be your best man, you want to consider whom you’re asking, they’re availability, and what you’re expecting from the “best man” title—that way, there are no misunderstandings or hurt feelings down the road.

Ok, so now that you know what to consider before you ask someone to be your best man for your wedding ceremony, let’s jump into the how—how to ask someone to be your best man.

Plan Around Your Favorite Activity

If you’re asking someone to be your best man, your relationship runs deep—and, chances are that there are hobbies, past times, or activities that you have a history of enjoying together. And those activities can make a great backdrop for asking someone to be your best man.

For example, if you and your best man-to-be have been golfing together for the past decade, asking him to be your best man on the golf course while you’re enjoying a round would be great. If you and your soon-to-be best man are both obsessed with a certain football team, you might invite him over to watch a game and ask him during halftime.

The point is, relationships are built on shared interests and activities—and asking your best man to be in your wedding while you’re both enjoying those shared interests and activities can be a great way to make your ask feel more personal.

Send Him a Card

How To Ask Someone To Be Your Best Man Photo Credit // Toni Jade Photography

Some people aren’t great with emotional conversations. If you’re one of those people—and you’re worried that you won’t be able to get the words out in person—you should definitely consider asking your best man to be in your wedding through a card.

There are plenty of different approaches that you can take when sending a “will you be my best man?” card. You can use the card as an opportunity to dive into why the person is so meaningful to you and why you want him to be your best man. You can take a more nostalgic route and use the card to highlight your favorite memories before asking him to be in your wedding party. Or, if you don’t want to get too emotional, you can infuse the card with humor or keep it super simple and just ask him to be your best man in a straightforward way.

Whatever you decide to include, sending a card can be a great way to ask someone to be your best man (if you can’t, or don’t want to, have the conversation in person). Plus, cards make for a great keepsake for your best man to remember the occasion by.

Give Him a Gift

If you’re not sure how to ask someone to be your best man, why not give him a gift—and let the gift do the asking for you?

There are TONS of “proposal” gifts out there that you can use to ask someone to be your best man (that literally say “will you be my best man?”, from personalized t-shirts to golf balls to whiskey glasses). Ideally, you’ll give your soon-to-be best man with something that he’ll use—and, even better, something that ties back to your relationship.

So, for example, if you and your best man are obsessed with coffee, a personalized coffee mug would make a great gift. If he’s more of a wine guy (or one of your favorite memories is a wine tasting trip that you took together), a personalized wine glass would be a better bet.

There’s a seemingly unlimited number of gifts that you can personalize to ask someone to be your best man—so just find the gift that feels like the best fit for you and your best man-to-be.

Just Ask

If all of this thinking and planning around how to ask someone to be your best man is stressing you out, don’t worry! You don’t need a plan, a gift, or a grand gesture to ask someone to be your best man; it’s also totally fine to, you know...just ask.

Your best man is a pretty important person in your life—and ultimately, he’s not going to care how you ask him to be in your wedding. He’s just going to care that you ask—and that he gets to be there to support you on your big day.

Asking someone to be your best man is an important question. And, with these tips, you have everything you need to “pop the question” and secure your best man’s place in your wedding party.

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