Who Should Be My Best Man?

Asking someone to be your best man is a big deal. The best man is expected to be by your side throughout the entire wedding process, from attending pre-wedding events to planning the bachelor party and providing support in the lead-up to the wedding day. Before you ask, it's important to consider who you're asking, what you're expecting from them, and whether they're the right person for the job.

There are many ways to ask someone to be your best man, from a simple conversation to a more creative approach. Some people prefer to ask in person, perhaps during a favourite shared activity, like playing golf or watching a football game. Others might opt for a handwritten note or card, a gift, or even a proposal box filled with items like cufflinks, a tie, or a personalised hip flask. Ultimately, the most important thing is to choose someone who is meaningful to you and who you want to support you on your big day.

Gifts: Send a gift box, a personalised item, or a bottle of their favourite spirit

Gifting is a great way to ask your best mate to be your best man. It's a thoughtful gesture that adds meaning to the experience and shows your appreciation and excitement for having your closest friends and family by your side on your big day. Here are some gift ideas to help you pop the question:

Gift Boxes

Gift boxes are a fantastic way to make a statement and show your thoughtfulness. You can curate a selection of items that reflect your friend's personality and interests, making it a memorable and personalised gesture. For example, you could include items like cufflinks, socks, ties, and a customised message. If you want to go the extra mile, present the gift box during a fun gathering, like a casual hangout or a groomsmen lunch, so that the unboxing adds a ceremonial touch.

Personalised Items

Personalised items always make a great impression as they show you've put extra thought into the item. From engraved wooden watches, monogrammed lighters, and customised tumblers to playful coffee mugs with caricatures, there are numerous ways to add a unique and special touch. You could even get creative and engrave their groomsmen invitation on their favourite bottle of spirits.

A Bottle of Their Favourite Spirit

A bottle of their favourite drink is a classic way to propose to your groomsmen. You could include a customised label with their new wedding title, or go a step further and engrave the invitation directly on the bottle. Accompany the bottle with a set of engraved cufflinks or a classy hip flask for an extra special touch.

In-Person: Ask during a shared activity, over dinner, or with a handwritten note

Asking someone to be your best man is a big deal. The best man is expected to be by your side throughout the entire wedding process, from attending pre-wedding events to planning the bachelor party and providing support to you and your partner. Therefore, it's important to consider who you're asking, their availability, and what you're expecting from them.

If you're unsure how to ask someone to be your best man, here are some ideas for doing it in person during a shared activity, over dinner, or with a handwritten note:

During a Shared Activity

Plan your proposal around your favourite shared activity. For example, if you and your best man-to-be have been golfing together for years, pop the question while enjoying a round of golf. If you're both fans of a particular football team, invite him over to watch a game and ask during halftime. Asking your friend to be your best man while engaging in a shared activity adds a personal touch to your proposal.

Over Dinner

Asking your friend to be your best man over dinner is a simple yet effective approach. You can either ask the question casually during the conversation or make it more formal by presenting them with a "will you be my best man?" card. You can include a handwritten note inside the card expressing why this person is meaningful to you and why you want them to be your best man.

With a Handwritten Note

If you're not comfortable with emotional conversations or prefer a more creative approach, a handwritten note is a great way to ask someone to be your best man. You can send a simple card with a thoughtful message or get creative with a personalised card, such as a scratch card or a "will you be my best man?" telegram. Include a nostalgic note highlighting your favourite memories or infuse the card with humour to make your friend smile.

Group Ask: Gather your groomsmen and pop the question to the whole group

Asking your friends to be part of your wedding party is an opportunity to show them how much they mean to you. Make it fun, thoughtful, and personal. Here are some ideas for asking your groomsmen as a group:

Group Dinner or Drinks

Gather your groomsmen for a dinner or drinks, then pop the question to the whole group. It’s a great way to celebrate the moment together. You can make it a casual get-together or a more formal event, depending on your preference and the dynamic of the group. This option allows you to create a memorable experience for your friends and gives them a chance to bond if they don't know each other well.

Sports or Game Day

If your group is into sports, consider asking them during a game. You can even wear personalised shirts or caps that say "Groomsman" or "Best Man" to make it more fun and memorable. This option is perfect if you want to incorporate your shared interest in sports into your proposal.

Creative Gifts

You can give them creative gifts that pop the question, such as:

• Customised bottles of their favourite spirits with an invitation engraved on them.
• Subscription boxes that represent your groomsmen or your shared interests.
• Cigars, which symbolise the unique sense of brotherhood between good friends.
• Customised cufflinks with a short message, phrase, or initials unique to each groomsman.
• A pack of compiled funny one-liners or proposal cards full of inside jokes.
• Starter kits with essentials like cufflinks, a bow tie or printed tie, and a small bottle of their favourite drink.
• Educational booklets on ties and different knot styles, especially if ties aren't part of their everyday routine.
• Directions to a nearby tailor or tuxedo service, printed on a card with a personal story and your invitation.

Remember, asking your groomsmen as a group is a great way to celebrate your friendships and create a memorable experience for everyone involved.

Cards: Send a simple card, or a funny or nostalgic message

Cards are a great way to ask your best mate to be your best man. They can be a good option if you're not great with emotional conversations or if you want to make your proposal more personal.

There are plenty of different approaches 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 them by your side on your wedding day. You can take a nostalgic route and use the card to highlight your favourite memories before popping the question. Or, if you don't want to get too emotional, you can infuse the card with humour or keep it super simple and just ask the question in a straightforward way.

• Scratch card: Add your best man's name and choose a balloon design to put his mark on it.
• Illustrated card: Opt for a simple, meaningful card that can be tailored to your heart's desire, from the details of your groomsman to the printed message inside.
• Chalkboard card: Go for a textured card with brown envelopes to make it feel more formal.
• Calligraphy card: Choose an affordable yet elegant card and tailor the script and envelope colour to suit your wedding theme.
• Secret message card: Why limit your best man to one envelope-opening experience when you could give him two?
• Contemporary card: Choose a card with contemporary hand lettering that stands out.
• Funny card: Send a lighthearted card that will put a smile on your best man's face, such as a tongue-in-cheek card that plays on the word "suit".

Whatever you decide to include in your card, make it personal and heartfelt. You can also include a small gift with the card, such as a bottle of their favourite spirit with a custom message or a set of cufflinks.

No Fuss: Just ask

If you're looking for a no-fuss way to ask your friend to be your best man, here are some simple and direct approaches:

Be Direct

Simply ask your friend if he would like to be your best man. A direct approach like this can be effective, especially if you know your friend well and are confident that he will accept. This method is straightforward and to the point, and it avoids any unnecessary stress or complications.

In-Person Conversation

While you can certainly ask your friend over text or phone call, it is generally considered more respectful and meaningful to have this conversation in person. Choose a quiet and private setting where you can both be comfortable and have a sincere discussion. This approach allows you to convey your thoughts and feelings more effectively and makes the moment more memorable.

Lead with Your Relationship

Begin the conversation by talking about your relationship and the value it holds for you. Express your appreciation for your friend and let him know how much you value his presence in your life. This will set the tone for your request and help him understand the significance of the role you are offering.

Explain Your Expectations

Before popping the question, it's important to be clear about what being a best man entails. Let your friend know what you expect from him, including his participation in pre-wedding events, planning the bachelor party, and providing support throughout the wedding process. This ensures that he understands the commitment and can make an informed decision.

Ask the Question

After laying the groundwork, it's time to pop the question. You can simply say something like, "Will you be my best man?" or "I would be honoured if you stood by my side as my best man." This direct approach conveys your request clearly and gives your friend the opportunity to respond.

Remember, the most important thing is to choose someone who you trust and who will be able to fulfil the duties of a best man. It's okay to keep it simple and direct—your friend will likely appreciate the sincerity and honesty of your approach.

Frequently asked questions