How to Ask Someone to Be Your Groomsman

Doing a Basic Invitation

Ask in person whenever possible. Receiving an invitation to be a groomsman is exciting. It also sends a meaningful message that you value your relationship with someone enough to ask that they stand beside you while you make one of the most significant commitments in your life. Accordingly, make your request personal by asking in person if you can. There doesn’t need to be any pomp and circumstance. Simply get together and say something like, “Hey man, our friendship has meant a lot to me over the years. I wanted to ask you if you’d we willing to join Carrie and I on our wedding day as a groomsman?” Keep in mind you can still send along a funny card or a thoughtful gift in the mail.

Write them a letter. If you’re not able to speak in person with all of your groomsmen, consider writing a letter to those you will ask by mail. Since a letter can be more personal than a phone call, this is preferable, especially for a close friend that lives further away. Be specific with something like, “I’m writing to invite you to join us on our wedding day as a groomsman.” Include a more personal message as well. For instance, say something about what your relationship with the recipient has meant, and why you want them to be at your wedding.

Send a reminder card. Even if you’re able to have the conversation in person, it’s worth sending a card with the details. Since you already spoke about it in person, the card will simply function as a tangible reminder, with important information like dates, location, and dress code. Choose or make a card that reflects your personality, an interest you share with your groomsman, or a design that fits with your wedding theme. Look at greeting card websites and wedding websites for examples of card designs. Many will allow you to order cards in a design you like and customize lettering and color schemes. If you haven’t finalized a date but want to nail down your wedding party, let them know what time of year you’re thinking. Get back to them about a specific day as soon as you determine one.

Asking Cleverly

Host an event and surprise your groomsmen. If possible, gather all the gentlemen you’re hoping will be your groomsmen and break the news in a celebratory manner. For instance, invite them over for a pot of your world-famous chili and a couple of hands of poker. Before they arrive, relabel a few bottles of beer with customized “Groomsman” labels and set them in each spot at the table with a koozie covering the label. Once everyone sits down, propose a toast and have everyone remove the koozies simultaneously. Verbalize your excitement by saying something like, "It'd really mean a lot to have you guys as my groomsmen."

Go the romantic route. It's not everyday you get to buy your friends roses. If they'll appreciate the humor or are just into flowers, consider sending a bouquet with a card saying something like, "Alexander.... be my groomsman?" Even better, send the bouquet to their home or, if you know they'd be okay with it, to their place of work.

Make a prank out of it. If your potential groomsmen are all over the country and you’ll be sending out snail mail requests, consider going the April Fool’s route. For instance, write, “Notice of Mandatory Attendance” on a formal looking envelope. This may get them scratching their heads as they nervously open your request, only to be relieved by the exciting content. Another idea: Send a plain envelope that reads “Important Instructions” on the exterior. Inside, include directions on how to tie a tie, as well as your folded request. Whatever you do, make sure the letter doesn’t look like spam. Hand-write their address. You don’t want them accidentally throwing it away!

Customizing Your Groomsman Requests

Make custom booze-themed labels. There are various websites that will help you design and order custom beer or liquor bottle labels. You can also design, print, and cut your own. Affix these directly to individual beer bottles with sticker paper, or hang more traditional cards around the necks of your groomsmen’ favorite liquor bottles. Either present these gifts in person or send them in the mail. They can be even be used to break the news, or as a follow-up to an in-person conversation. For instance, you might customize labels that look like name tags with text like "Groomsman Tucker."

Give your groomsmen something to wear on your big day. Part of accepting the gig as your groomsman is agreeing to wear whatever outfit you want them to wear at your wedding. If you so happen to have style-minded friends, they may appreciate a customized something-or-other that will fit with the suits you’ve chosen. For instance, get your buddies bow ties that reflect each of their individual styles. Get that wannabe lumberjack buddy a plaid bow tie and your alma mater’s biggest fan a bow tie with the team mascot on it.

Include a long-lasting customized gift. While booze and a cigar are the traditional groomsman gifts, consider getting something a bit longer-lasting to include with your groomsman requests. For instance, a simple but classy tie clip or a lighter monogrammed a buddy’s initials is something they’ll likely keep for the rest of their lives. Cufflinks are a classic example, and can be tailored to each groomsman. For instance, have custom-made cuff links with your favorite picture of your buddy inset, or an inscription of an inside joke between the two of you.

Acknowledge financial costs if necessary. Getting down to brass tacks: it costs money to be a groomsman. Tux rental alone can be expensive, not to mention peripheral costs like a wedding gift, travel costs, and a potential bachelor party. In situations where you know cost may be a factor regarding someone’s ability to be your groomsman, don’t ignore the issue. If you have a friend that may not be able to afford being your groomsman but you’d like them to be, considering covering the cost yourself.