The Perfect Timing To Ask Your Best Man

Asking someone to be your best man is a big deal. It's an important role, and it's a special way to honour your relationship with someone. While there's no set timeline for when to ask your best man, it's a good idea to give them a heads-up at least eight months to a year before the wedding. This gives your best man time to plan and prepare for their duties. When it comes to who you choose, it's ultimately up to you. Your best man should be someone you trust and feel comfortable with, whether that's your brother, best friend, or even your sister or female cousin. There are no rules, so go with your gut and pick the person who is most important to you.

When to ask

There is no one right time to ask your best man to be your best man. Some people ask their best man as soon as they are proposed to, while others wait until they have set a date for the wedding. It is generally a good idea to ask your best man eight months to a year before the wedding to give them ample time to adjust their schedules and fulfill their responsibilities. This is especially important if your best man will be playing a major role in the wedding planning process.

However, it is important to choose your best man carefully. Your best man should be someone you trust and who has been in your life for a long time. It is also important to consider the responsibilities of the best man and whether your chosen candidate is up to the task. The best man is typically responsible for organizing the bachelor party, giving a toast at the wedding, and providing support to the groom on the big day. If you have any doubts about your chosen candidate, it may be worth considering someone else or delegating some of the responsibilities to other groomsmen.

Ultimately, the decision of when to ask your best man is a personal one, and you should do what feels right for you.

Who to ask

When it comes to choosing your best man, it's important to select someone who is close to you and who you can rely on. While it's common to choose a brother or a close friend for this role, ultimately, the best man should be the person who is most important to you, regardless of their gender. You may even decide to have two best men if you can't choose between two people or want to divide the responsibilities.

• The responsibilities of the best man: The best man will play a pivotal role in the planning and execution of pre-wedding events and will offer support to the groom. They will also give a speech at the wedding and be in charge of the rings. If you have a friend who is particularly good at planning or public speaking, they may be a good fit for this role.
• The dynamics of your friendship: Consider how long you have known your potential best man and the nature of your relationship. A long-time friend who has been in your life for a while may be a safer choice than a new friend, as friendships can shift over time.
• Compatibility with your fiancée: While it's your choice, your fiancée may have preferences or dealbreakers when it comes to the best man. For example, if one of your friends has disrespected your fiancée in the past, it's probably best to avoid choosing him. However, if your fiancée simply doesn't like the way he chews his food or thinks he drinks too much, you can stand your ground and make the choice you want.
• Their availability: Ask your groomsmen at least eight months to a year before your wedding to give them ample time to adjust their schedules and fulfill their responsibilities.
• Your intuition: Ultimately, go with your gut when choosing your best man. Pick someone you trust and who you believe will support you and enhance your special day.

Remember, you can also break the mould and ask a female friend or family member to be your "best woman" if that feels right for you.

How to ask

Asking your best friend to be your best man is an important moment, so it's worth putting some thought into how you'll do it. Here are some ideas for how to ask your best friend to be your best man:

Timing

First, consider the timing of your proposal. It's a good idea to ask your best man at least eight months to a year before the wedding. This gives them time to plan and prepare, especially if they need to adjust their schedule or fulfil certain responsibilities.

Be Formal

While you don't need to make a huge event out of asking your best man, it's also not something you should do casually. Rather than emailing or texting, call them or speak to them in person.

Groomsman Starter Pack

One way to ask your best friend is to gift them a wedding day starter pack. This could include items like a shaving kit, cufflinks, a tie bar, and socks.

Groomsman Box

Alternatively, you could create a groomsman box. Start with a cool tin or wooden box, then fill it with items they'll love, such as a small bottle of their favourite liquor, an expensive cigar, and an engraved lighter.

"Will You Be My Best Man?" Cards

You could invite your friend over to watch a game or have dinner, then give them a "Will you be my best man?" card. You could attach something small to the card, like a shot glass, or pop the question on an item they'll be using that evening, like a coaster or napkin.

Say it with a Bottle

Get a full-sized bottle of their favourite drink and attach a funny or sentimental note asking them to be your best man. You could also have a custom label made for the bottle or get it engraved.

A Bouquet of Roses

Want to embarrass your friend? Send them a bouquet of roses with a note asking them to say "yes" to being your best man.

A Subscription Box

If your friend doesn't live close by, you could sign them up for a subscription box. Think about their favourite things and choose a box that matches their interests. Include a personalised note asking them to be your best man.

A Memorable Experience

Sometimes, sharing an experience is the perfect way to ask your friend to be your best man. This could be going to a sports event, a day at the races, or a gourmet dinner. You could also incorporate inside jokes or themes from your shared experiences into the proposal.

A Handwritten Letter

Consider writing a heartfelt, personalised letter to your friend, explaining why you've chosen them to be your best man and what their support means to you.

Remember, it's always a good idea to choose your best man carefully and to check in with your partner before asking. You'll want to agree on the total number of people in the wedding party, and while you may not veto each other's choices, communicating can help you work out any differences.

Proposal gifts

While there are no rules about when to ask your best man, it's a good idea to plan to ask everyone eight months to one year in advance. It's also important to choose your groomsmen wisely—opt for those who have been in your life for a long time rather than a new friend.

Now, onto the fun part—how to ask your best man in a clever way. Here are some thoughtful proposal gifts to help you pop the question:

Groomsman Starter Pack

Give your best man a wedding day starter pack. Include items like a shaving kit, cufflinks, a tie bar, and socks. This is a subtle way to hint that you're about to ask them to be a groomsman.

Groomsman Box

Create a groomsman box with a cool tin or wooden box as the base. Fill it with items your best man will love, such as a small bottle of their favourite liquor, an expensive cigar, and an engraved lighter. You can also include a "Will you be my best man?" card inside.

Bottle of Booze

Get a full-sized bottle of their favourite alcoholic beverage and attach a funny or sentimental note to the front asking them to be your best man. You can also have a custom label made for the bottle or get it engraved.

Bouquet of Roses

Want to embarrass your best man at work? Send them a bouquet of roses with a note asking them to say "yes" to being your best man.

Subscription Box

Sign your best man up for a subscription box filled with their favourite treats, whether it's candy from their childhood, Japanese snacks, or cinema memorabilia. Include a personalised note asking them to be a part of your special day.

Best Man Proposal Cards

There are plenty of creative cards available, from funny "Will you be my best man?" cards to unique options like scratch cards or golf balls with the message printed on them.

Personalised Gifts

Personalised gifts are always a great option. You can get them a customised hip flask, beer mug, watch, cufflinks, or a bottle opener.

Remember, the key is to make it personal and suit your best man's personality. Good luck with your proposal!

Timing

The timing of your "best man" proposal is just as important as the proposal itself. While there is no one-size-fits-all approach, there are some general guidelines and considerations to keep in mind. Here are some tips to help you time your proposal perfectly:

Long Engagements

If you're planning a long engagement, there's no rush to secure your best man right away. Friend dynamics can shift over time, and you don't want to be in an awkward position of having to backtrack on your offer. It's generally a good idea to ask your best man and groomsmen anywhere between eight months to one year before the wedding. This gives them ample time to plan, adjust their schedules, and fulfil their responsibilities. It also shows your appreciation for their role in your special day.

Short Engagements

If your engagement and wedding date are closer together, you may need to act more swiftly. Some people choose to ask their best man as soon as they get engaged, especially if they want to include them in the early planning stages. Others may wait until a few months before the wedding, but be mindful that you don't want to leave it too last minute, as your chosen best man will likely need time to prepare and perhaps make travel arrangements.

Choosing the Right Person

Take your time to choose the right person to be your best man. Consider your closest friends, siblings, or cousins. It's important to select someone who has been a constant presence in your life and who you trust wholeheartedly. Remember, your best man doesn't have to be a man. You can ask your sister, cousin, or female best friend to take on this role as your "best woman" or "groomslady."

Communicate with Your Partner

Before asking anyone to be your best man, it's a good idea to communicate with your partner and agree on the total number of people in the wedding party. While it's ultimately your decision, involving your partner in the discussion can help prevent any misunderstandings or hurt feelings later on. Remember, it's your special day, and you want to be happy with your choices.

Making the Proposal

When it comes to proposing to your best man, don't feel pressured to make a grand event out of it. A simple yet heartfelt approach is often the best. Consider calling them or speaking with them in person instead of just sending a text or email. You can even create a "Will you be my best man?" card or include a small gift to make the moment more special.

Frequently asked questions