Best Man: Asking Your Friend The Right Way

Asking someone to be your best man is a big deal. It's a big job, and it's important to choose the right person for the role. Once you've decided who to ask, there are many ways to pop the question. You could plan around your favourite activity, send a card, give a gift, or simply just ask. If you're not sure how to go about it, here are some ideas to get you started.

Plan a proposal around your favourite shared activity

Planning a proposal around a shared activity is a great way to make your best man proposal feel more personal and meaningful. Here are some ideas to help you pop the question to your best friend:

Golfing Buddy

If you and your best friend have been golfing buddies for years, why not pop the question while enjoying a round of golf? You could ask them to be your best man as you tee off, or as you relax at the 19th hole. This setting will add a fun and casual vibe to your proposal.

Sports Fanatic

If you and your friend are obsessed with a particular sports team, you can incorporate this passion into your proposal. Invite them over to watch a game and pop the question during halftime. Alternatively, you could take them to a live game and ask during a break in the action. This proposal idea combines your shared love of sports with a memorable moment.

Coffee Connoisseurs

Do you and your friend bond over your mutual love of coffee? If so, a coffee-themed proposal could be perfect. You could invite them to your favourite coffee shop and pop the question over a freshly brewed cup of Joe. Or, if you're feeling creative, you could spell out "Will you be my best man?" with coffee beans!

Movie Marathoners

Are you and your friend movie buffs who love nothing more than a good film marathon? Turn this shared interest into a proposal by creating a custom movie night invitation that pops the question. Or, if you're feeling extra creative, you could edit the proposal into the ending of their favourite film and pop the question as the credits roll.

Cooking Companions

If you and your friend love trying out new recipes and experimenting in the kitchen, a cooking-themed proposal could be perfect. You could present them with a personalised apron that says "My Best Man" or cook their favourite meal and pop the question over dessert.

Remember, the key is to incorporate your shared interests and activities into the proposal to make it unique and memorable. Good luck with your proposal!

Send a card

Sending a card is a great way to ask your friend to be your best man, especially if you're not great with emotional conversations. You can take a few different approaches with your card, depending on your relationship with your friend and how you want to ask the question.

If you want to express how meaningful your friend is to you and why you want him to be your best man, you can use the card as an opportunity to dive into these feelings. You can also take a nostalgic route and use the card to highlight your favourite memories before asking him to be in your wedding party.

If you don't want to get too emotional, you can infuse the card with humour or keep it super simple and just ask him to be your best man in a straightforward way. Whatever you decide to include, a card is a great keepsake for your friend to remember the occasion.

• Scratchcard: Add your friend's name and choose a balloon design to put his mark on it.
• Chalkboard card: A textured card with a brown envelope that feels more formal.
• Calligraphy card: An affordable yet expensive-looking card, where you can tailor the script and envelope colour to your wedding theme.
• Top Job card: Like a friend appraisal, this card conveys what your friend means to you.
• Secret message card: Why limit your friend to one envelope-opening experience? This card provides two!
• Contemporary card: Contemporary hand lettering makes this elegant card stand out.
• Funny card: A tongue-in-cheek card will put a smile on your friend's face.

Give them a gift

Asking someone to be your best man is a big deal. It's a big job, and you want to make sure that the person you're asking is the right person for the role. Before you pop the question, it's important to consider the person you're asking, their availability, and what you expect from them.

If you're unsure of how to ask your friend to be your best man, why not give them a gift? Here are some gift ideas to help you pop the question:

Gift Ideas

• Engrave a bottle of their favourite spirit with a personalised message asking them to be your best man. You could also include a custom mug or glass for them to pour their drink into.
• Subscription box with a note inside. You can select a box that represents your friend and your relationship. Many subscription boxes have free or inexpensive introductory offers, so you can just use the trial period to secure a box for them.
• Cigars are a classic symbol of brotherhood, so why not secure a cigar to a piece of quality stationery with a letter asking them to be your best man? Alternatively, you could gift them a personalised humidor or cigar case.
• Custom cufflinks with a short message, phrase, or their initials. You could tell them that this is how you're asking them to be your best man, and that you're excited to see them dressed to the nines on your big day.
• Funny one-liners or proposal cards full of inside jokes. At the end of the cards, include a humorous letter noting that they have an important assignment, with pictures of fingerprints and a space for them to sign.
• Starter kit with the essentials, such as cufflinks, a bow tie or printed tie, and a small bottle of their favourite drink. You could also include a unique gift box that matches their personality and interests.
• Educational booklet on ties and different knots, especially if ties aren't a part of their everyday routine. You can give them the card and tell them that you're excited to see how good (or bad) their tie knots are at your wedding.
• Print-out of a tailor or tuxedo service in their area, with a personal story on the back about how excited you will be if they accept your invitation.
• Bouquet of liquor with miniature bottles of their favourite spirits suspended on sticks inside a vase or pot. Don't forget to leave a note asking them to be your best man!
• Invitation card—a simple yet effective way to ask your friend to be your best man, especially if they live far away.

Write a letter

Writing a letter to ask your friend to be your best man is a great way to make your request feel more personal. Here are some tips to help you craft a meaningful letter:

Consider Your Relationship

Before you put pen to paper, reflect on your relationship with your friend and what you appreciate about them. Think about the hobbies, pastimes, or activities you enjoy doing together, as well as your favourite memories and inside jokes. This will help you infuse your letter with warmth and personality.

Dive into Why They're Meaningful to You

In your letter, express how much your friend means to you and why you want them by your side on your wedding day. Talk about the qualities that make them important to you and how they have supported you in the past. You can also mention how excited you are to have them be a part of this new chapter of your life.

Get Creative with Your Wording

There are many ways to approach the wording of your letter. You can take a nostalgic route and highlight your favourite memories together, or you can focus on the future and how much it would mean to have them as your best man. If you're feeling nervous about the request, you can add a touch of humour to lighten the mood.

Include a Personalised Gift

If you want to go the extra mile, pair your letter with a thoughtful gift. Consider your friend's interests and hobbies when choosing the gift. For example, if they're a coffee connoisseur, a personalised coffee mug would be perfect. Or, if they're a wine enthusiast, a customised wine glass would be a memorable gift. You can even include "will you be my best man?" on the gift for a creative touch.

Plan a Special Delivery

Think about how you want to deliver your letter to make it even more memorable. You could handwrite the letter and send it via mail to give it an old-school feel. Or, if you want to do something more personal, plan a day to hang out with your friend and give them the letter in person. This could be while you're engaging in a shared activity or simply over a cup of coffee.

Remember, the most important thing is to express your genuine sentiments and let your friend know how much their presence at your wedding would mean to you. Good luck with your letter!

Ask them in person

Asking your friend to be your best man is a big deal. It's a big job, and you want to make sure that they feel special when you ask them. While there are many creative ways to ask your friend, such as with a card, gift, or even a "groomsman starter pack", asking in person is a great way to make the moment memorable and meaningful. Here are some tips on how to ask your friend to be your best man in person:

Pick the Right Person

Being a best man is a big responsibility, and you want to make sure you choose someone who is up for the task. Consider your friend's availability and whether they have the time and energy to devote to your wedding planning. It's also a good idea to choose someone who has been in your life for a long time, as they are more likely to still be close to you in the months leading up to your wedding.

Plan a Special Outing

Plan a one-on-one hangout session with your friend. This could be an activity that you both enjoy, such as golfing or watching a football game. This will make the moment more personal and allow you to create lasting memories together. During the outing, you can bring up the topic of your wedding and how much their friendship means to you.

Lead the Conversation to Your Relationship

Start by talking about your relationship and how you feel about your soon-to-be spouse. This will help set the tone and express your emotions. You can say something like, "I think I found the right person, and I can't wait to spend the rest of my life with them." This will also help transition into talking about your friend and how much you value their friendship.

Express Your Appreciation

Let your friend know how much you appreciate them and how honoured you would be if they stood by your side on your wedding day. You can say something like, "You've been such a great friend to me over the years, and I would be honoured if you could be my best man." Asking in person will make your friend feel valued and appreciated.

Be Prepared for Their Response

Remember that your friend may need time to think about the responsibility, especially if they have a busy schedule or other commitments. Be understanding if they need some time to consider your request, and let them know that it's okay if they can't commit. You can also offer to discuss the details and expectations of the role to help them make an informed decision.

Keep It Casual

While asking your friend to be your best man is a big deal, you don't need to make it a formal or overly dramatic event. A simple, heartfelt conversation will do the trick. You can even make it a lighthearted moment by saying something like, "She said 'yes,' now it's your turn!" Just remember to be sincere and express your genuine desire for them to be a part of your special day.

Frequently asked questions