Asking Your Best Mate To Be Your Best Man

Asking someone to be your best man is a big deal. It's a big job, and the person you choose will be supporting you throughout the entire wedding process. From attending pre-wedding events to planning the bachelor party, your best man will be by your side until your wedding day. So, how do you ask someone to be your best man? While some people opt for a simple conversation, others prefer to make a fuss. You could plan a special day out or give a gift with a card. Whatever you decide, make sure you choose someone capable, sociable, and discreet.

Gifts: whisky, a flask, a cigar, cufflinks, a card, or a personalised item

Asking your best mate to be your best man can be nerve-racking, but there are many creative ways to do it. Here are some ideas centred around gifts of whisky, a flask, a cigar, cufflinks, a card, or a personalised item:

Whisky

Whisky is a classic gift, and it can be a great way to propose the idea of being your best man. Consider pairing it with a roaring log fire and perhaps some chocolates or cheese to match. You could also opt for a whisky-themed gift, like whisky-flavoured marmalade, to be enjoyed the morning of the wedding.

Flask

A flask is a quintessential groomsman gift, and it can be personalised for an extra special touch. This gift can be presented ahead of the wedding to give your best man some Dutch courage before his speech.

Cigar

A cigar can be a great gift for a cigar lover, but it can be challenging to find the right one. Consider visiting a reputable tobacconist and telling them your budget and any preferences you know your friend might have. You could also include a cigar cutter or a personalised cigar accessory, like a leather cigar holder with their initials.

Cufflinks

Cufflinks are a sleek and understated gift that can be monogrammed with your friend's initials. They can be paired with a suit and tie to kit out your best man early or presented as a standalone gift.

Card

There are many card options to choose from, ranging from funny to stylish. You can opt for a simple, meaningful card or a personalised card with your friend's name and a balloon. If you want to be more subtle, consider a card with a chalkboard design or one with a secret message.

Personalised Item

Personalised items can make your proposal more cinematic and memorable. Consider a colourful print with inside jokes or a movie-style art print that makes your intentions clear. Other ideas include a monogrammed glass, a pocket watch, a silk pocket square, or a photo frame with a picture of the two of you.

In-person: take them out for a meal, a round of golf, or a drink

Asking someone to be your best man is a big deal, so you'll want to make sure you do it in a way that feels meaningful and memorable. One way to make your request feel more personal is to plan it around a shared favourite activity. This could be anything from grabbing a meal or a drink to playing a round of golf or watching a game together.

If you and your friend have been golfing together for years, for example, you could ask them to be your best man while you're out on the golf course, enjoying a round. Similarly, if you and your friend bond over your love for a particular sports team, you could invite them over to watch a game and pop the question during halftime.

If you're more of a foodie duo, you could take them out for a meal or a drink at their favourite restaurant or bar. This option might be especially fitting if you and your friend bond over trying new foods or drinks, or if you have a lot of inside jokes about food and drinks.

When asking your friend to be your best man, it's important to be clear about what you're asking of them. Being a best man is a big job, and it's crucial that your friend understands the responsibilities involved before they agree to take on the role. These responsibilities might include planning the bachelor party, providing emotional support in the lead-up to the wedding, and helping the groom and groomsmen with their wedding attire choices.

So, if you're planning to ask your friend to be your best man over a meal or a drink, it's a good idea to be mindful of the setting and the timing. You don't want to spring this question on them in the middle of a busy restaurant or bar, for example, as they might feel put on the spot and unable to give you a considered answer. Instead, try to choose a quiet spot where you can have a private conversation, and perhaps save the question for the end of the meal, when you're both feeling relaxed and happy.

Remember, the most important thing is that your friend feels honoured and excited to be your best man. So, whether you're asking them over a fancy dinner or a casual drink, make sure you express how much their friendship means to you and why you want them by your side on your big day.

By post: send a card, or a telegram

If you're not great with emotional conversations, you can ask your best man through a card or telegram. There are plenty of different approaches to 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 to be your best man. You can take a more 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.

Cards are a great way to ask someone to be your best man, especially if you can't or don't want to have the conversation in person. Plus, they make for a great keepsake for your best man to remember the occasion by.

There are a variety of cards available on Etsy, ranging from funny to classy and simple to nostalgic. You can also personalise your card to make it even more special. For example, you can add your best man's name and choose the colour of the balloon on a "Will You Be My Best Man?" scratch card from Chips & Sprinkles. Or, if you want to add a photo, you can use a postcard-style card from The Knot.

If you want to go old-school, you can even send a telegram. Imperial Telegrams offers a "Will You Be My Best Man?" telegram for £14, featuring vintage stamps.

Group outing: plan a group activity, like a camping trip, or a night at your favourite bar

Planning a group activity is a great way to ask your best man to be part of your wedding. Here are some ideas to make it special:

Choose an activity that suits your group's interests

If your group loves the outdoors, why not plan a camping trip? You can get everyone involved in setting up tents, collecting firewood, and cooking over an open fire. It's a great opportunity to bond and create lasting memories. Alternatively, if your crew prefers city life, organise a night out at your favourite bar. Reserve a table or section just for your group, and let the drinks and conversation flow.

Make it personal

Consider what type of relationship you have with your friends. Are you all passionate about a particular activity or sport? If so, incorporate that into your group outing. For example, if you're all avid golfers, book a round of golf at a scenic course. If you're water enthusiasts, plan a day of surfing or kayaking. By tailoring the activity to your group's interests, you'll create a more meaningful and enjoyable experience for everyone.

Add a thoughtful touch

While the group setting is perfect for popping the question, you can also add a personal touch by giving your best man a gift. It could be something related to the activity, like a customised cooler bag for the camping trip or a hip flask for the bar night. Or, you could give him a token of your friendship, like a pocket watch or a book you think he'd enjoy.

Keep it casual

When inviting your friends, frame it as just another fun hangout with the guys. You don't need to make a big deal out of it. Keep the atmosphere light and casual, and your friends will feel more comfortable opening up and having a good time.

Lead by example

As the organiser, you set the tone for the group outing. If you want your friends to engage and have meaningful conversations, take the initiative. Share a story or an update about your life, and ask for their thoughts. By leading the way, you'll create a safe and welcoming space for everyone to connect and socialise.

One-on-one: ask them in person, but individually

Asking your best friend to be your best man can be a daunting task, but it can be made easier if you ask them in person, but individually. Here are some tips on how to do this:

Choose a suitable time and place

Locate a quiet and private place where you can have an uninterrupted conversation. Ensure that you and your friend are both available and free from distractions. Consider their schedule and choose a time when they are likely to be relaxed and receptive to your request.

Prepare what you want to say

Before the meeting, take some time to think about what you want to say and how you want to ask them. You can even practise in front of a mirror or with another friend to ensure that you are confident and clear in your delivery. Consider the following points:

• Express your appreciation for their friendship and explain why you value them.
• Explain why you are getting married and what the wedding means to you.
• Tell them why you want them to be your best man. Share specific reasons and examples of why they are important to you.
• Ask them if they would be willing to take on the responsibility and honour of being your best man.

Create a special moment

Make the moment memorable and meaningful. You could consider presenting them with a small gift, such as a personalised card, a bottle of their favourite drink, or a token that symbolises your friendship. This will show that you have put thought and effort into asking them, making them feel valued and appreciated.

Be prepared for their response

Your friend may be thrilled and accept immediately, or they may need time to consider the responsibility. Be respectful of their response and give them the time and space to make a decision. If they accept, celebrate the moment together and discuss the next steps, including any duties they will need to fulfil as the best man. If they decline, respect their decision and thank them for their honesty. Remember that they may have valid reasons for saying no, such as financial constraints or personal commitments.

Follow up

After your conversation, follow up with a text or call to reiterate your appreciation and excitement about having them by your side on your wedding day. This will reinforce your friendship and ensure that they feel valued and included in your special day.

Frequently asked questions