Separating The Best Man: When And Why To Do It

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 the soon-to-be married couple. While there are no hard-and-fast rules about how to ask someone to be your best man, it is generally considered important to do it in person and to give them a gift. It is also a good idea to plan your best man proposal around your favourite shared activity, whether that's playing golf or watching a football game. This will make your proposal more personal and help to celebrate your friendship.

Ask in person

While you can certainly ask someone to be your best man over the phone or via email or text, there's something special about asking in person. Here are some tips and ideas for popping the question in person:

Firstly, consider the location. You could ask your best man-to-be in a place that holds special meaning for the two of you, like your favourite bar or a spot that's significant to your friendship. This will add a thoughtful touch to your request. If you can't be in the same place, consider a video call so that you can still see each other and make the moment more personal.

Next, think about how you want to phrase the question. You can keep it simple and direct, such as "I'd be honoured if you would be my best man." Or, if you want to make it more lighthearted, you could say something like, "I'm getting married, and I need your help not to screw it up! Will you be my best man?" Make sure to ask the question in a clear and direct manner so that your intentions are understood.

To make the moment more memorable, consider incorporating a small gift or token to mark the occasion. For instance, you could present your best man with a personalised gift, like a bottle of their favourite liquor, a nice hip flask, or a special keyring. This not only adds a tangible element to your request but also gives them something to remember the day by.

Finally, be prepared for their response. Chances are, they will be thrilled and honoured to accept your request. However, if they need time to think about it or discuss it with their partner or family, respect their decision and give them the space to do so. It's important to understand that being a best man is a big commitment, and they might have a lot to consider before giving you an answer.

Remember, asking in person allows you to create a memorable moment and strengthen your bond as friends. It shows that you value their presence and support on one of the most important days of your life. So, take the time to plan and make it a special moment for both of you.

Make it personal

Asking someone to be your best man is a big deal, so it's important to make it personal. While there's no need to make a grand gesture, it's a good idea to put some thought into how you'll ask. Here are some ways to make it personal:

• Plan around a shared activity: If you and your best man-to-be share a hobby or favourite pastime, use this as a backdrop to your proposal. For example, if you're both golf buddies, ask him while you're out on the course. If you're both fans of the same football team, invite him over to watch a game and pop the question at halftime.
• Write a card: If you're not great with emotional conversations, a card can be a thoughtful way to express yourself. You can use the card to highlight your favourite memories, explain why your friend is so meaningful to you, or simply ask the question in a straightforward way.
• Give a gift: Let the gift do the talking by presenting your friend with a "proposal" gift. From personalised t-shirts and golf balls to whiskey glasses and hip flasks, there are plenty of options to choose from. Consider choosing something that ties back to your relationship, like a personalised coffee mug if you're coffee connoisseurs or a wine glass if you've shared a wine-tasting trip.
• Handwritten note: A heartfelt, personal letter is a timeless way to ask your friend to be your best man. Reflect on your friendship, share why having them by your side on your wedding day matters, and explain what you expect from them.
• Surprise dinner or drinks: Gather your groomsmen for a surprise dinner or drinks and pop the question to the whole group. It's a great way to celebrate the moment together and will make your best man feel special.

Plan around a shared activity

Planning a shared activity with your best man is a great way to ask them to take on the role and can make for a memorable moment. Here are some ideas for planning a shared activity to pop the question:

Go for a Hike or Camping Trip

Plan a camping trip or hike with your best man and pop the question during the trip. You could present them with a personalised hip flask or a pocket knife with their initials on it and ask them to be your best man. Alternatively, you could give them a "survival kit" with items like a flashlight, a multi-tool, and a personalised matchbox, and include a note asking them to be your best man.

Go for a Round of Golf

If your best man is a golf enthusiast, plan a round of golf with them and use this opportunity to ask them to take on the role. You could give them a golf-themed gift, like a box of golf balls or a golf towel with a personalised message, and ask them to be your best man.

Have a Drink Together

Plan a drinks night with your best man and use this opportunity to ask them to be a part of your wedding. You could give them a bottle of their favourite drink or a set of beer mugs with a personalised message as a gift. If you want to make it more light-hearted, you could give them a "Will you be my best man? scratch card" or a funny card that suits their sense of humour.

Take Them Out for Dinner

Take your best man out for a nice dinner and pop the question over a good meal. You could give them a gift like a pocket watch or a tie with a personalised message, or you could simply ask them over dinner and follow it up with a thoughtful gift later.

Plan a Cycling Trip

If you and your best man are cycling enthusiasts, plan a cycling trip together and ask them to be your best man during the trip. You could give them a cycling-themed gift, like a book about epic bike rides or a personalised water bottle, to mark the occasion.

Give a gift

Asking someone to be your best man is a big deal, so you might want to consider giving them a gift to mark the occasion. This could be something related to a hobby or activity you both enjoy, or something more personal. Here are some ideas:

Gifts

• A personalised print or card asking the question
• A monogrammed glass
• A bottle of whisky or another spirit
• A hip flask
• A pocket watch
• A tie
• Cufflinks
• A wallet
• A book
• A t-shirt, golf balls, or a whisky glass with "will you be my best man?" printed on it
• A coffee mug or wine glass

Other Ideas

If you don't want to give a gift, you could plan an activity that you both enjoy and ask during that. For example, if you like golfing, you could ask while out on the course. Or, if you prefer something more low-key, you could simply ask in person or send a card.

Ask yourself: who is capable, sociable, and discreet?

Asking someone to be your best man is a big deal. It is important to consider who you are asking, what you are expecting from them, and whether they are the right person for the job. The best man is expected to be your right-hand man, supporting you during wedding planning, throwing your bachelor party, and standing next to you when you say your wedding vows.

So, ask yourself: who is capable, sociable, and discreet?

Your best man should be capable of taking on the responsibilities of the role. They will be expected to participate in the entire wedding process, from attending pre-wedding events to planning the bachelor party, and providing support to you and your partner. If you expect your best man to help with wedding planning, consider whether they have the time and energy to devote to this. For example, your best friend might have just had a new baby, so while you may still want them as your best man, you may need to lower your expectations of their availability.

Your best man should also be sociable, as they will be responsible for keeping guests entertained and making sure everyone gets along. They will need to be able to balance a large group of people and keep them organised, so consider whether your chosen candidate is good at herding people and keeping the peace.

Finally, your best man should be discreet. They will be in a position of trust, knowing the ins and outs of your wedding and personal life, so it is important that you choose someone who can be relied upon to keep sensitive information to themselves.

While it is ultimately your choice, it is worth bearing in mind that your partner may never forgive you if you get this wrong!

Frequently asked questions