How to Ask Someone To Be Your Groomsman

Although your wedding might be centered around marrying your soulmate, having your closest friends by your side can make the event truly special. Just like their female counterparts, groomsmen do more than just stand beside the groom on the big day. In addition to planning the bachelor party and renting a tux, they’ve also got to write a memorable speech.

By finding a unique or creative way to ask your groomsmen, you’ll be showing that you appreciate them right off-the-bat. Figuring out how to ask someone to be your groomsman can be a little challenging, but here’s what you can do:

When Do You Ask?

Before you even begin to think about how to ask your groomsmen to stand by you, the first question you’ve got to answer is when you plan on asking. Many people might assume that you should ask immediately after you announce your engagement. However, there’s no reason you need to secure your groomsmen immediately.

It’s not unusual for engagements to last a year or even two years. The close friendships you might have at the beginning of your engagement might not always be the same ones you have at the end. The last thing you want is to end with a lineup of groomsmen that you feel as if you barely know or feel as if your close friends are getting left out.

Although you shouldn’t wait until the last minute, don’t feel pressured to immediately ask anyone if you plan to be engaged for a couple of years. Once you’ve set a date for your wedding, you can begin thinking about dropping the question.

Typically, it’s best to try and ask your groomsmen around eight months or a year in advance. Not only does this timeframe give your groomsmen plenty of time to plan a bachelor party and get everything they need, but it’s not too long that your friendships will shift too much.

For destination weddings that might be happening in other countries or thousands of miles away, you might need to ask your groomsmen sooner so they can arrange travel plans.

If your engagement is relatively short, and you plan to be married within a few months, it might be smart to ask your groomsmen right away.

Who Should You Ask To Be Your Groomsmen?

Once you know when you should ask your groomsmen, the next obstacle you have to conquer is figuring out who you should ask. Picking out your groomsmen can be a challenge—these are the people that will stand beside you during one of the most important moments of your life. Your groomsmen also have a certain amount of responsibility as well, so it’s crucial to pick people who are up to the task. For instance, a friend who lives thousands of miles away might have trouble planning a bachelor party for you.

One thing to consider is how many bridesmaids there will be. At many weddings, the groomsmen and bridesmaids pair up and walk down the aisle together. If you don’t have as many groomsmen or you have too many, it can look awkward. If it’s possible, it’s always smart to try and plan your number of groomsmen around the number of bridesmaids there will be.

The number doesn’t have to exactly match, but having eight bridesmaids and only two groomsmen might look a little odd.

Does My Future Brother-in-Law Need to Be One of My Groomsmen?

One question that some grooms might be curious about is whether or not they need to include their future brother-in-law in the wedding party. If you’re already close with your brother-in-law, the answer might be an immediate yes.

However, if you’re still getting to know your brother-in-law, it’s really up to you. Many people do choose to include their in-laws in the wedding party to start things off on the right foot, but it’s not a requirement.

If your bride chooses to ask your siblings to be in her wedding party, then it might be courteous to include her brother in yours. Ultimately, if you think that leaving your future brother-in-law out might cause drama or result in hurt feelings, it might be better to ask him to be a groomsman.

Can a Female Friend Be a Groomsmen?

If you’ve got a female friend that you’re close to, it’s only natural that you’d want her by your side on the big day. While including a woman as a “groomsman” wasn’t always typical, it’s becoming more common. It’s not unusual for a groom to ask a female friend, cousin, or even a sister to serve as a “groomswoman” or even as the “best lady.”

However, if your friend doesn’t feel comfortable as a groomsman, another way to include her is by asking her to be a bridesmaid.

If I Was a Groomsman For Someone, Do I Need To Ask Them to Be Mine?

One of the more awkward questions that a groom has to consider when picking his wedding party is whether or not to include people he’s been a groomsman for. You might not feel as close to that person, but many people worry about causing drama or hurt feelings by not asking.

While it can be a little awkward to deal with, your groomsmen should always be the people you feel closest to. If you haven’t maintained a friendship with someone whose wedding party you were in, you shouldn’t feel obligated to ask. You want your groomsmen slots to be filled up by people you truly care about, not people you feel obligated to.

How to Pick Which Friends You Want to Ask

If you’re having issues narrowing down which friends you’d like to ask, one thing you can do is make a list of the people closest to you. The people on that list can be family members or close friends that you’ll want to be involved in the wedding process with you.

Some people might also base their selection on which friends get along (and which ones don’t). If you have a close friend who is going to cause a lot of drama with the rest of your wedding party, you might want to consider not asking them.

Other factors to consider are location and how responsible your friends are. Asking a friend that lives thousands of miles away to be a groomsman might not be worth it unless you’re extremely close. Since your wedding party is involved in various events (like the rehearsal dinner and bachelor party), it’s important to make sure your groomsmen will be able to attend them.

Responsibility might not be the biggest factor, but it is worth thinking about. Your groomsmen, especially your Best Man, will be responsible for planning your bachelor party and attending several events before the wedding. If you already know that your friend won’t be able to handle that kind of responsibility, it might not be worth it to ask them.

What if One of My Friends is Upset That I Didn’t Ask Them?

Although it doesn’t happen all the time, some friends might be hurt that they weren’t asked to be part of your wedding party. For instance, a friend that included you as one of their groomsmen years ago might be upset that they didn’t make the cut in your wedding.

Unfortunately, you won’t be able to make everyone happy, and it’s unrealistic to let everyone who wants to be a groomsman become one. What you can do is apologize, and explain that it was a difficult decision.

It might be tempting to give in to someone’s demands, but you shouldn’t have to stand beside anyone that you don’t want to.

What if Someone Doesn’t Want to Be My Groomsman?

While it’s more likely that someone would be upset about not getting asked, it’s possible that someone might decline when you ask them to be apart of the wedding. This isn’t necessarily because they don’t want to—they might not be able to afford it or have another obligation they have to attend to.

In some cases, a groomsman might accept your offer but then back out a few months later if something else comes up. Along with being disappointing, losing a groomsman can be difficult if it changes the ratio of how many people you have in your wedding party.

Although you can just continue with your wedding party the way it is, you can also try and find someone to step in for the missing groomsmen as well. Having a “back-up option” in case anyone isn’t able to do it can be a smart idea. Most of the time, you want your back-up groomsmen to be someone who lives nearby and won’t need to travel far for the wedding.

However, asking a back-up can be tricky if it’s really close to the wedding. They might already have plans, or it might be challenging for them to rent a tux before the big day.

What if Two of My Groomsmen Don’t Like Each Other?

Although you might already know who your groomsmen will be, one thing that can be tricky to navigate is conflict and drama. If a couple of your groomsmen don’t like each other, it can make group events like the bachelor party feel awkward and tense rather than celebratory.

If your groomsmen can’t put their issues behind them for the sake of the wedding, you might need to sit down and have a conversation with them. You might not be able to completely resolve the conflict with one conversation, but hopefully you’ll be able to help them come to enough of an agreement that they won’t cause further conflict or drama during the big day.

If they can’t come to an agreement, try reminding them that this event isn’t about them and that you’d like them to remain cordial for the sake of the entire wedding party.

If there are still plenty of issues and one groomsman seems to be causing most of the tension, you can ask that person to sit out. While this option is less than satisfactory since it means you’ll be losing someone you care about, it might be worth it if that person is causing drama and tension within your wedding party. When you’re standing at the altar, the last thing you want to worry about is someone causing a scene.

How To Ask Someone to Be Your Groomsman

Now that you understand how to pick out your wedding party, it’s time to think about how you’ll drop the question. While brides often make big displays or gestures when they ask their bridesmaids, groomsmen are known to be a little more casual.

However, there is such a thing as being too casual when asking someone to join your wedding party. Since these people are going to stand by you on the big day and support you throughout the process, you want to ask them in a way that shows your appreciation.

For instance, sending a text or an email might downplay the seriousness of what you’re asking. If the person you want to ask isn’t in town or lives somewhere else, you should at least try calling them and having a conversation on the phone.

Some of your groomsmen might already know they’ll play a role in the wedding party, but that doesn’t mean you still can’t find a creative way to ask. Here are a couple of different things you can do:

Plan a Guys’ Day

One way to make asking your groomsmen special (and convenient) is by inviting all of your future groomsmen over for a dinner party, a game, or another shared activity you all enjoy. Once you’ve got everyone gathered in the same place, you can hand out cards or papers that say, “Will you be my groomsmen?”

If that doesn’t seem to fit your style, you can always make a short speech and announce that you’d like to ask everyone there to be in your wedding party. Regardless of how you go about it, getting everyone in the same place will help the entire group bond while also saving time. Instead of having to address everyone on separate occasions, you can ask them all at once.

Make a Groomsmen Starter Pack

It’s not unusual for people in the wedding party to receive tiny gifts as a thank you for their participation on the big day. If you want to surprise your groomsmen while also showing how much you appreciate them, try making a starter pack.

You can fill a box with items they might need for the wedding—such as dress socks, a tie, or cuff links. Not only will your groomsmen find the items useful, but they’ll probably be touched by the gesture as well.

While they might quickly understand what the package is for, you can also include a card with the question, “Will you be my groomsman?”

Create a Special Groomsmen Package

If creating a starter pack doesn’t feel personal enough, you can always try creating special groomsmen packages. Instead of filling the box with items that your groomsmen will need for the wedding, you can pick out tiny trinkets or gifts that remind you of that specific person.

Your future groomsmen might be a little confused as to why they’re receiving a gift, but at the bottom of the box, you can place an index card with, “Will you be my groomsman?” Depending on the person, you can also try coming up with a clever line that relates to the items in the box or an inside joke.

Say it With Flowers

If you really want to have a little fun with it, you can always try asking your groomsmen by sending them flowers and attaching a note. Ordering a bouquet of roses and sending them to your friend’s workplace might embarrass them at the moment, but chances are that you’ll be able to laugh about it afterward.

Not to mention, sending anyone flowers is still a thoughtful sentiment, and your friend or family member will likely appreciate the gesture.

Gift Them Their Favorite Alcohol

If you aren’t sure that your groomsmen will appreciate flowers, you can always try gifting them their favorite type of alcohol instead. A full-size bottle of their favorite liquor or wine with a lighthearted note might be all you need to make the moment special.

While it takes a little bit more planning, some companies allow you to customize your own label. When your friend looks at the bottle, they’ll see the question, “Will you be my groomsman?”

The only issue with this gesture is that it can quickly become pricey. If you plan to buy your entire wedding party their own bottles (which may include customized labels), you could end up shelling out a few hundred dollars.

A more cost-effective solution is to either buy the entire group a full-sized bottle of alcohol. Or, if your wedding party is only going to be a few groomsmen, it might be worth it to buy everyone their own bottle.

Use Personalized Shot Glasses or Mugs

This method tends to go along with purchasing a bottle of alcohol. If you aren’t a fan of the custom label, you can always pick up a regular bottle for everyone and make personalized shot glasses or mugs.

The next time that everyone is together, you can pull the glasses out and ask everyone if they want a drink. Chances are, it won’t take long for everybody to realize they’re drinking out of groomsmen glasses.

Make it a Proposal

Your wedding might be one of the most important moments of your life, but there’s no reason why you can’t inject a little humor into the situation. If you truly want to confuse your groomsmen and create a memorable moment, don’t be afraid to get down on one knee. The difference, however, is that you’ll be asking this person to be a part of the wedding—not your bride.

For a little extra humor, you can use a fake ring or another piece of jewelry to make the groomsmen’s proposal seem more authentic.

Sign Your Friend Up For a Subscription

It might be a little more time-consuming, but another way to surprise your wedding party is by signing your groomsmen up for a subscription they like. This could be magazines, candy, or even some type of cinema memorabilia. Depending on the service you choose, you can pick how many months you sign your friend up for. Many of these subscription services allow you to include a personalized note as well.

However, like purchasing alcohol, this endeavor can quickly become expensive if your wedding party extends beyond a few people. Not to mention, you also need to find different subscriptions that each of your groomsmen will like.

Although this tactic can be unique, it might be right if you only plan to have a couple of groomsmen.

Make a Scratch Off Card

If your groomsmen enjoy scratching off lottery tickets, they might appreciate this tactic. Plenty of companies will allow you to make customized scratch cards. Instead of winning money, your groomsmen will scratch away to reveal the question you want to ask.

Use Embarrassing Moments to Your Advantage

If you’ve been friends with your groomsmen for several years, chances are that you have plenty of inside jokes and embarrassing moments that you can use against them. If creating a custom label or personalized shot glass doesn’t seem interesting enough, you can try putting an embarrassing photo of your groomsmen on the label.

Or, if you can’t find a photo you think is good enough, you can always try and find a way to include inside jokes with the gift.

What if My Groomsman Lives Far Away?

One obstacle that can be challenging to overcome is figuring out a special way of how to ask someone to be your groomsman when they live far away. If you can’t see them in person, it makes it difficult to ask while you’re hanging out together or even to do something goofy such as fake-propose.

However, there are still plenty of fun and interesting ways you can ask your friends that live far away. Tactics like signing your friend up for a subscription still work perfectly fine. You can also still send the groomsmen starter pack or special box in the mail as well.

Sending a bottle of alcohol in the mail might be a little risky, but it is possible if that’s what you truly want to do.

What if I’m on a Budget?

There are plenty of creative and interesting ways to ask your groomsmen to stand beside you at the wedding, but many of them can quickly become pricey. For instance, creating starter packs for everyone or picking up personalized mugs can get expensive if you have more than a few groomsmen in your wedding party. However, you don’t need to sacrifice creativity just because you’re on a budget. Here are a few tactics you can pull off without spending tons of money:

Keep it Simple and Ask Everyone at Once

Personalized mugs and cuff links are fun, but sometimes, you don’t need anything extra to make the moment feel memorable. When you invite your groomsmen over for a fun day of bonding or to watch the big game, don’t feel shy about asking them all at once.

If you want to, you can even write a short speech so that they understand how much the moment means to you. While it won’t include personalized shot glasses, it will still feel just as special. Not only will your groomsmen get to know one another if they don’t already, but everyone can bond together at once.

Sing a Song

Putting your songwriting skills to the test won’t cost you a cent. One goofy way you can make the moment special is by singing your groomsmen a song. Although you can do this while they’re all in one place, you can also sing to them separately as well.

If you don’t think you’ll be able to come up with an entirely new song on your own, you can try changing the lyrics of an existing song to fit what you want to say.

Not Every Method is Right For Every Groomsman

Before you start ordering flowers or creating custom labels, it’s important to consider which method will work for your specific groomsmen. For instance, a close friend might find the fake proposal to be hilarious, while the brother-in-law you barely know might find it odd.

Ultimately, it’s important to make sure that the method you choose to ask with won’t make your groomsmen uncomfortable. Buying everyone a bottle of alcohol might not be a great idea if one of your groomsmen doesn’t drink. If you aren’t sure if it’s a good idea, you can always run it by your future spouse.

Regardless of how you decide to ask your groomsmen, the most important thing is that you’ll have your closest friends and family members standing beside you on the big day.

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