Proposing To Your Best Mate: The Best Man Question

Asking your best friend to be your best man can be nerve-racking, but it doesn't have to be. While it's a big job, it's also a big honour, and one that most friends will be happy to take on. So, how do you ask? Well, there are a few ways to go about it. You could plan it around your favourite shared activity, like playing golf or watching a football game. You could also send a card, which is a great way to make the moment more personal and give your friend a keepsake. Or, you could give them a gift, like a personalised t-shirt or whisky glass, and let the gift do the talking. But, if all that feels like too much, you can just ask your friend in person – no fuss, no frills.

Asking in-person vs. sending a card

Asking your best mate to be your best man can be nerve-racking. You want to impress your pal and mark the moment, but you also want to consider their availability and what you expect from them.

Asking in Person

Asking your best mate to be your best man in person is the traditional way to do it. It's a good idea if you want to make the moment more personal and memorable. Here are some ways to ask your best man in person:

• Plan around your favourite shared activity. For example, if you've been golfing together for years, ask while enjoying a round of golf.
• Have a surprise dinner or drinks with your groomsmen and pop the question to the whole group.
• If your group is into sports, consider asking them during a game by wearing personalised shirts or caps that say "Groomsman" or "Best Man".
• Go for a hike or do some other activity that you usually do together.

Sending a Card

If you're not great with emotional conversations, you might want to consider asking your best man through a card. This option also gives you the opportunity to dive into why the person is so meaningful to you and why you want them to be your best man. Here are some ideas for sending a card:

• Include a handwritten, heartfelt, and personal letter reflecting on your friendship.
• Take a nostalgic route and highlight your favourite memories before popping the question.
• Include a simple "Will you be my best man?" card with your personal message inside.
• Infuse the card with humour or keep it straightforward if you don't want to get too emotional.

Whether you decide to ask in person or send a card, remember that your best man is important to you, and you want them by your side on your big day.

Choosing a gift

Gifts are a great way to ask your best mate to be your best man. It's a special moment that deserves a special and original gift. A present shows not only your appreciation and respect but also the personal bond you share. It is a gift they will cherish and remind them of the special moment.

If you're stuck on what to get them, here are some ideas:

Personalised Gifts

Personalised gifts are a perfect way to ask your future best man. It shows that you've gone the extra mile and that you want to make the moment memorable. Here are some ideas for personalised presents:

• Print: A movie-style art print or a colourful print with in-jokes is a great way to make your intentions clear.
• Glassware: A gilded monogram glass is a more subtle personalisation option. You could also get them a personalised hip flask or whisky glass.
• Stationery: A "Will You Be My Best Man? telegram" is a unique and old-school way to pop the question.
• Pocket Watch: An engraved pocket watch is a classy and timeless gift.
• Clothing: You could get them a personalised t-shirt or a pair of wedding socks. If you've decided on your wedding suit, you could also get them a tie.
• Card: You could give them a simple card or a funny card that says something like "You'd Rock It In a Suit".
• Food and Drink: You could get them a personalised beer package, wine, champagne, or non-alcoholic alternatives.

Gifts Based on Their Interests

If your best man has a favourite sport, you could buy them gear or accessories. If they're into golf, for example, you could get them some golf balls that say "Will You Be My Best Man?". Or, if they're a coffee or tea lover, you could get them a personalised mug or tea set.

Gift Boxes

You could also create a personalised gift box with a mix of items, such as socks, sunglasses, a flask, a pocket knife, or a book that relates to a shared interest.

Practical Gifts

If you want to give them something practical that you know they'll use, you could opt for a gift card or a nice wallet.

Traditional Gifts

If you want to go for a traditional gift, you could get them a flask or a watch.

Planning around a favourite activity

If you and your best man pal share a favourite activity, planning your proposal around it is a great way to go. Here are some ideas to pop the question "Will you be my best man?" in a fun and memorable way:

Let's say your favourite activity is golfing. You could organise a round of golf at a local course and invite your prospective best man along. As you tee off, have custom golf balls made with the question "Will you be my best man?" printed on them. After you've taken a few swings, offer your friend one of the special golf balls and ask them to take a swing. They'll be surprised and delighted to see the question printed on the ball and will surely say yes!

Or, if you both enjoy craft beer, why not arrange a brewery tour and tasting? Get in touch with a local brewery and see if they can accommodate a private tour for you and your friend. As you sample the different brews, casually bring up the topic of your wedding and how you're looking forward to planning the big day. Then, instead of a traditional bottle opener, use a personalised bottle opener with the "Will you be my best man?" engraved on it to open one of the beers. Present it to your friend as a keepsake and a token of your friendship.

For an outdoorsy type of favourite activity, like hiking, plan a hike to a scenic spot, perhaps a waterfall or a mountain peak, and bring along a picnic lunch. As you take in the views and enjoy your meal, bring up the topic of friendship and how much you value having them by your side. Then, present them with a personalised compass, engraved with the question, "Will you be my best man?" It symbolises that you want them to help you navigate through this important journey in your life.

If you both enjoy cooking or trying new cuisines, sign up for a cooking class together. Choose a class that features a type of cuisine or dish that you both love. As you're chopping, stirring, and following the chef's instructions, casually bring up the subject of your wedding plans. Then, present your friend with a customised apron that reads, "I couldn't tie the knot without you. Will you be my best man?" It's a fun and unique way to pop the question while also enjoying a delicious culinary experience.

These are just a few ideas to get you started. The key is to incorporate your shared favourite activity into the proposal in a meaningful and creative way. So, think about what you both enjoy doing together, and use that as a foundation to plan a memorable "best man" proposal!

Considering who to ask

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 all the pre-wedding events to planning the bachelor party and providing support to you and your partner. Before you ask someone to be your best man, it's important to consider who you're asking, their availability, and what you're expecting from them.

For example, if you expect your best man to spend weekends helping you choose a wedding venue, negotiate with vendors, or run other wedding-related errands, you might not want to ask your best friend who just had a new baby. They may not have the time or energy to devote to your wedding planning.

However, if you want a close friend to be your best man, you can still ask them, but you may need to lower your expectations. For instance, they might not be able to run wedding-related errands with you, but they may be open to meeting for coffee once a month to go over logistics and see if there's anything they can help with when they have spare time.

The key is to choose someone who means a lot to you, whether it's your brother, a best friend, a college mate, or a close colleague. It's also important to ensure that the person you choose is someone you respect, appreciate, and want to represent you on your big day.

• Availability and Commitment: Consider the person's availability and whether they can commit to the responsibilities of being a best man. Are they able to attend pre-wedding events, plan the bachelor party, and provide support when needed?
• Shared Interests and Activities: Think about shared interests and activities that you and your potential best man enjoy together. Asking them while engaging in one of these activities can make the moment more personal and meaningful.
• Communication Style: Reflect on the person's communication style. If they are not great with emotional conversations, consider asking them through a card or a gift. This can make it easier for them to respond and avoid any awkwardness.
• Practical Considerations: Keep in mind any practical considerations that may impact their ability to fulfil the role. For example, do they live nearby, or are they located far away? Are they usually reliable and organised?

Remember, choosing a best man is about selecting someone who you trust and who will be honoured to stand by your side on your wedding day. It's a chance to celebrate your friendship and create lasting memories together.

How many groomsmen to ask

When it comes to deciding how many groomsmen to ask, there is no one-size-fits-all answer. The number of groomsmen you choose should reflect the scale of your wedding. For a large, formal event, a bigger wedding party of five or more groomsmen can create a grand, symmetrical look. On the other hand, for smaller, intimate weddings, a group of 2-4 groomsmen feels more personal and manageable.

One of the main considerations is whether you want to balance the number of groomsmen and bridesmaids. While it's not a strict rule, matching the number on both sides can make for smoother logistics, especially during the ceremony and in photographs. Discuss with your partner how many bridesmaids they're planning to ask, and adjust your groomsmen count accordingly.

However, don't feel locked into an exact match. If your fiancée has three bridesmaids and you'd like four groomsmen, that's fine too. What matters most is that each person in your wedding party is there for a reason and that you focus on choosing the people you feel closest to and want by your side throughout the planning process and on your wedding day.

• Logistical considerations: The more groomsmen you have, the more coordination will be required, from planning bachelor parties to organizing fittings and keeping track of everyone's roles. The size of your venue may also be a factor—a large wedding party in a small space might feel cramped.
• Cost: Each groomsman will need a suit, so the more you invite, the higher the cost. If you're paying for your wedding party's outfits and accommodation, this can quickly add up.
• Relationship strength: Ultimately, the decision should be guided by the strength of your relationships. Choose the people who mean the most to you and who you trust and want by your side throughout the planning process and on your wedding day.

Remember, there is no magic number when it comes to how many groomsmen to ask. Focus on selecting the people who are most important to you and who will make your wedding day even more special.

Frequently asked questions