10 Ideas to Ask Someone to be Your Groomsmen

Some fun ways to ask someone to be a groomsman at your wedding.

By Deanna deBara

groomsmen at a wedding
Photo by Kindred Photography

As a groom, deciding whom you want to be in your wedding party is an important part of the wedding planning process. But, once you know whom you want to ask to be your groomsmen, the next big item to check off your wedding to-do list is asking them.

The pressure to ask someone to be a groomsman in a meaningful and memorable (or, perhaps, humorous) way may be on—and with good reason. Asking your brother, family member, friend, or the other important men in your life to stand by your side as you say your “I do’s” is a pretty big deal. That being said, once you have a plan, it really isn't that difficult. To help you get there, we've compiled a few of our favorite ways to ask your beloved family members and best friends to be your groomsmen. Plus, who you'll want to consider asking. For all of the much-needed info, look below.

Who Do You Ask to Be Your Groomsmen?

First thing's first: Let's talk about who you might want to ask to be in your company. A wedding's groomsmen typically consists of the groom's closest friends and family members. This can include their father, grandfather, their fiancée's father and grandfather, siblings, cousins, extended family members, and close friends. In short, it's any of the people you want to stand by your side as you get married. There isn't a typical number of groomsmen, although usually there are around five.

You aren't limited to men, either. If you have close friends or family members that aren't men, you can without a doubt still ask them to stand at your side and support you through this exciting milestone (and maybe plan your bachelor party).

Now that we've got that covered, let's dive into the fun stuff. Below we unpack ten different groomsmen proposal ideas that are bound to end in a resounding, yes!

Ways to Ask Someone to be Your Groomsmen

1. Send a Formal Invitation

You send out save the dates and wedding invitations, so why not send out a formal invite to your soon-to-be groomsmen?

An invitation can be a great, thoughtful way to ask someone to be a groomsman. By writing your invite to the wedding party, you can be sure that you say everything you want to say to your future groomsmen—which can sometimes be challenging during a face-to-face conversation (when emotions are running high, you might stumble over your words or forget something you wanted to communicate, like an important memory or the reason you want that particular person to be in your wedding party). Plus, when you send a formal invitation, your groomsmen have a tangible item that they can keep to remember the experience.

2. Give a Gift That You Know They’ll Love...

Sending a groomsmen proposal gift that you know will be meaningful to your close friend or family member—along with a note that says something along the lines of “I know this means a lot to you, and you mean a lot to me. Want to be my groomsman?”—can be another great way to ask someone to be in your wedding party.

For example, if your future groomsman is really into basketball, you might get them tickets for the two of you to see his favorite team. If he’s a big reader, you might find the first edition of his favorite book. If he’s really into wine, you can give them a bottle that he’s had his eye on. So on and so forth, with a thoughtful and unique gift for each person.

The point is, giving a gift that you know will mean a lot to your close friend shows that you've taken special care in planning giving said gift or hangout—and can be a great segue into asking them to stand by you on your wedding day.

3. ...Or, Give a Gift Directly Related to Your Wedding

Another great idea for asking someone to be at your wedding is to give them something directly related to your wedding. Dor example, if you’re asking someone to be a groomsman, you might give them a monogrammed pair of cufflinks, a pocket square or tie that matches your wedding color palette, or a cigar specifically meant to light up after you walk down the aisle. Likewise, you can gift them a drink glass, beer mug, or shot glasses they'll be happy to raise a toast with, complete with a "Will you be my groomsman?" custom label. When you give them the gift, explain that they’ll need it for your big day—and ask them to be your groomsmen.

How to Ask Someone to be Your Groomsmen Photo Credit // Christopher Duggan Photography

4. Ask All Your Groomsmen at Once

If you’re having a larger wedding party or the thought of going through the process of asking someone to be your groomsmen multiple times feels overwhelming, you can always knock it all out at once—and ask all of your future groomsmen to be in your wedding at the same time.

The key to success with this strategy is to make it an event. Invite all of your soon-to-be groomsmen to get together for something fun—such as a backyard BBQ, hiking adventure, brewery tour, or even your engagement party. (Or, if your wedding party is spread out across multiple locations and getting together in person isn’t possible, you can schedule a get together on Zoom.)

Once you have everyone together and having fun, you can give a short speech on why these people are such an important part of your life and why you want them to stand by your side on your wedding day—and then ask everyone collectively if they’ll be your groomsmen.

Chances are, you’ll be met with a resounding “yes”—at which point everyone can go back to the fun and festivities. Asking everyone at once also provides the entire group with a sense of familiarity and comradery, which will make future wedding-related get-togethers (like your bachelor party) all the more fun.

5. Send Each Person a Groomsman Gift Box

Many things go into being a well-rounded and supportive groomsman—and each one is entirely personal to you, your relationships, and your wedding day. That being said, what better way to ask those closest to you to join your wedding party than by gifting them a gift box that will prepare them for all of the fun to come? Themed groomsmen boxes are not only an opportunity to give your close friends and family members a few nice things, but can also provide a sneak-peak at all of the celebrating you're about to do together.

If you're stuck on theme ideas, you can easily tie your groomsmen gift boxes into your wedding theme. Look to your venue, location, and the type of celebration you're throwing to inspire the items you put in each box. For example, a groomsman for a beach wedding may need sunscreen, a nice pair of shades, and a drink to hydrate with (like some of their favorite liquor). A future groomsman at a more formal affair may be happy to find a bow tie, bottle opener, and craft drink in his gift set. In any case, we highly suggest including some tissues for a good laugh (or cry).

6. Ask With an Accessory They Can Wear

It isn't rare that you see brides-to-be gifting their bridesmaids elegant jewelry or similarly wearable gifts such as shoes, bags, or hair accessories. If your budget allows, consider giving your groomsmen-to-be a similarly stylish gift that they'll appreciate and be able to sport on the big day. Bonus points if it's easily rewearable, too. A major upside: You have plenty of options, from affordable to splurge-worthy. We recommend looking into cufflinks, watches, dress shoes, bow ties or ties (added bonus: everyone can match), chic or fun pocket squares, suspenders, socks, and—for the especially fancy—cologne.

Every gift doesn't have to perfectly match, either. For example, if you want to ask your loved ones to be your groomsmen with a snazzy tie, consider purchasing them in an array of colors that fit your wedding color scheme. Then match a color to each person, based on their personalities or what they typically like to wear. The same idea can work for bow ties, ties, pocket squares, and socks. That being said, we love matching group wristwatches and cufflinks just as much. Simply package your chosen accessory into a nice box with a handwritten (or typed-out) note and send in the mail or hand-deliver. What better way to tell your to-be groomsmen to suit up?

7. Say it With a Cigar

For many years, cigar smoking has been associated with celebrations, successes, and personal achievements. One such occasion that often sees groups—in particular, groomsmen—light up cigars is weddings. Doing so as a group is usually done to commemorate the celebration. As an added bonus, it brings your side of the wedding party (and whoever else is allowed to join in) together for some time.

In honor of this tradition, ask those closest to you to be your groomsmen by presenting them with a special cigar. We recommend securing each to a piece of high-quality paper (preferably with something like, "your service as a groomsman is requested" on it) or placing it within a nice envelope. If you can gather all of your potential groomsmen in one place, you can even present them as a group and ask everyone at once. Then, of course, have a celebratory smoke.

8. Do it With Humor

So, a formal invitation or request just isn't your style. Perhaps—and, in that case, we're betting it's likely—it isn't your future groomsmen's style, either. No worries. Not everything involved in your wedding planning has to be formal. In fact, asking people to be in your wedding party is one of your opportunities to go all-out and showcase your personality (you know, along with your bach party and the like). If you gauge that your loved ones would more so appreciate a good-natured joke or pun, by all means, use this ask as an opportunity to share one.

This can be done in a few ways, but the easiest is by card. A few of our favorite one-liners include, "You'd probably scrub up well," "This could've been a text, but will you be my groomsman?," and "You're being promoted from wingman to groomsman." If you want to get a bit more personal, include inside jokes between you and each person you're asking. You're sure to get some good laughs, which is a great sign for all of the celebrating ahead.

9. Be Over-the-Top

Speaking of humor, something that is sure to get a kick out of your friends and family is making your groomsman proposal completely over-the-top. We're talking roses, a dramatic lead-up and question, and quite possibly putting everyone on the spot. All in the name of a meaningful, yet funny and easy-to-pull-off groomsman request. One of our favorite options, here, is to have a bouquet of flowers delivered to each person's home or place of work. All the better if it's a bouquet of romantic red roses. Have a personalized note placed inside, dramatically asking each person if they'll be an important part of your wedding party. We love a good, Will you... be my groomsman? (or, alternatively, will you be my best man?).

You can even go all The Bachelor, get everyone together, and hold an impromptu rose ceremony, if you're eager to make a spectacle. You're sure to have the whole room suppressing laughter as you repeatedly ask if they'll accept your groomsman proposal. How's that for the most dramatic groomsman proposal ever?

10. Just Ask

There are a ton of fun and creative ways in which you can ask someone to be your groomsmen. But, if that’s not your style, no worries; you can always, you know, just ask.

Chances are that the people you’re asking to be your groomsmen are some of the closest people to you in the world. The way you ask a good friend to be at your wedding doesn’t matter; they don’t need a bunch of bells and whistles or pomp and circumstance. The only thing that matters is that you want them to stand with you on one of the most important days of your life—and just asking them to be your groomsmen simply and straightforwardly is 100 percent enough.

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