Best Man: Asking The Right Way

Asking someone to be your best man is a big deal. The best man is expected to support you during wedding planning, throw your bachelor party, and stand next to you when you say your wedding vows. 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. When it comes to popping the question, there are several ways to do it. You can plan an activity that you both enjoy, such as golfing or watching a football game, and ask during that time. Alternatively, you can send a card, either as a simple question or infused with humour and nostalgia. If you want to give a gift, there are many proposal gifts available, such as personalised t-shirts or whiskey glasses. Ultimately, your best man will just be happy that you asked and that he gets to be there to support you on your big day.

Plan around a shared activity

Planning your "groomsmen proposal" around a shared activity is a great way to make your request more personal. Here are some ideas to consider:

Choose an activity that represents your friendship

If you and your future groomsman share a hobby or interest, plan your proposal around that. For example, if you both enjoy golfing, take them out for a round of golf and pop the question during the game. Other ideas could include going fishing, attending a baseball game, or playing video games together. This approach will make your proposal feel more natural and organic.

Invite them to an event or outing

Plan an outing or activity that has special meaning for both of you. It could be a day out on the slopes, a round of golf, or even a paintball or pickleball session. You could also invite them to see your favourite sports team play, or a performance by a comedian or band you both love. This shared experience will create a memorable backdrop for your proposal.

Organise a group activity with all your groomsmen

If you're planning to have multiple groomsmen, consider inviting them all to a group activity. This could be a casual meal at a favourite restaurant, or a fun activity like go-karting, inner tubing, white water rafting, or bungee jumping. These types of activities encourage socialisation and will create a fun and relaxed atmosphere for your proposal.

Plan a "man meal"

If you have multiple groomsmen to ask, consider hosting a "man meal". Gather all your groomsmen-to-be at a favourite restaurant and ask them all at the same time. This setting provides an opportunity to raise a glass and celebrate your friendships. It's also a great way to ensure that no one feels left out.

Go for a nature walk or hike

Getting out into nature can be a great way to connect with your friends and create a peaceful setting for your proposal. Plan a group hike or a stroll in a beautiful natural setting. You could also go fishing or simply sit by a pool or hot tub, which can encourage conversation and create a relaxed atmosphere.

Remember, when asking someone to be your groomsman, you're honouring your relationship and asking them to play an important role in your wedding. By planning your proposal around a shared activity, you can make the moment more personal and memorable for both of you.

Send a card

Sending a card is a great way to ask someone to be your best man, especially if you're not great with emotional conversations. You can take a few different approaches when sending a "will you be my best man?" card.

One option is to use the card as an opportunity to express your feelings and explain why this person is so important to you. This can be a great way to let them know how much you value your relationship and why you want them by your side on your wedding day. You can also take a nostalgic route and use the card to highlight your favourite memories together. This will not only make your request more personal but also remind them of the special moments you have shared.

If you don't want to get too emotional, you can keep the card lighthearted and humorous. Injecting some humour into your card can make it more engaging and memorable. Alternatively, you can keep it simple and straightforward by just asking the question in a direct and concise manner.

Whatever approach you choose, sending a card is a thoughtful way to pop the question. It shows that you have put time and effort into your request, and it also gives your best man-to-be a keepsake to remember this special occasion by.

• Scratchcard: Add your best man's name and choose a balloon design to make it more personalised.
• Illustrated card: Opt for a card that can be tailored to your liking, from adding details about your groomsman to including a printed message inside.
• Chalkboard card: Go for a card with a textured finish and brown envelope for a more formal feel.
• Calligraphy card: Choose an affordable yet elegant card and customise the script and envelope colour to match your wedding theme.
• Secret message card: Why stop at one envelope when you can give your best man two? Prolong the excitement with a card that has a secret message inside.
• Contemporary card: Opt for a card with contemporary hand lettering that stands out.

Give a gift

Giving a gift is a great way to ask someone to be your best man. It can be a fun and thoughtful way to pop the question and will make for a memorable moment. Here are some ideas for gifts that will help you ask that important question:

Personalised Gifts

A unique and special way to ask your best man is by giving them a personalised gift. This could be something like a printed t-shirt, a mug, or a hip flask with the words "Will you be my best man?" on it. You could also give them a customised item related to a shared interest, such as a golf ball or a whiskey glass. Other ideas include a pocket watch, a tie, or a set of cufflinks. If you want to add a fun element, you could give them a scratch card with their name on it and a balloon to pop.

Food and Drink

If your best man-to-be enjoys a tipple, why not give them a bottle of their favourite spirit with a custom label or engrave the invitation directly onto the bottle? You could also give them a selection of beers or a fine single malt whisky. If they're more of a foodie, you could treat them to a box of chocolates or a selection of cheeses.

Experience Gifts

If you and your best man share a hobby or interest, you could give them an experience-based gift related to that. For example, if you both love golf, you could plan a round of golf and ask them during the game. Or, if you're both into cycling, you could gift them a book about epic bike rides and ask them to go on a cycling trip with you.

Gift Boxes

If you want to go all out, you could create a gift box with a variety of smaller gifts inside. This could include items like a pocket knife, a flask, a tie, cufflinks, a book, a wallet, or a selection of snacks. You could even include a card with a handwritten note from you, asking them to be your best man.

Remember, when choosing a gift, it's important to consider your friend's interests, availability, and what you expect from them as your best man. Good luck with your proposal!

Ask in person

Asking someone to be your best man is a big deal. It's a big job, and you're asking someone to be by your side throughout the entire wedding process. So, it's important to consider who you're asking, what you're expecting from them, and whether they're the right person for the role.

If you're asking someone to be your best man, your relationship is likely to be a deep one, and there will be hobbies, pastimes, or activities that you have a history of enjoying together. Asking your best man while you're both enjoying these shared interests and activities can be a great way to make your request feel more personal. Here are some ideas for how to ask someone to be your best man in person:

• Lead the conversation towards your relationship and how much you appreciate your soon-to-be best man. Let them know that you would be honoured if they stood by your side.
• Plan a one-on-one hangout session with the person you want to ask. This could be an activity you both enjoy, such as golfing, watching a football game, or going for a bike ride.
• If you and your friend are both obsessed with a certain football team, invite them over to watch a game and ask during halftime.
• If you and your friend enjoy golfing together, ask them to be your best man while you're out on the golf course enjoying a round.
• If you're both into cycling, plan a 'bromantic' pre-wedding bike trip and pop the question then.
• If you enjoy drinking whisky together, give them a bottle of single malt and ask them the question.
• If you're both foodies, get some steaks on the barbecue and ask them to be your best man by way of a personalised fire pit.
• If you're both into craft beer, get some interesting beers and ask them the question after a few drinks.
• If you're both into cheese, get some seasonal cheeses and ask them the question while you're enjoying them.

Buy their tux

When asking someone to be your best man, you're essentially saying, "You're important to me, and I want you with me throughout this entire process." It's a big job and a big ask, so it's important to consider who you're asking and what you're expecting from them.

One way to ask someone to be your best man is to gift them their wedding attire. Being a groomsman can be costly, so offering to cover their wedding suit when you're picking them out is a smart alternative to spending hours shopping for the perfect proposal gift.

• Timing: While you can rent a tux, buying a properly made tux will last for years and can be worn to any semi-formal event. It's important to get the timing right, as black-tie is evening wear, though it can be worn to an afternoon event if the festivities continue into the evening.
• Jacket: The tuxedo jacket is the cornerstone of the outfit. Traditionally, you have two colour options: black or midnight blue, made of wool with silk-faced lapels. Modern variations include dark tones like deep purple or maroon, or a fabric like velvet. The lapels should be peaked or in a shawl style, never notched, and faced with silk or grosgrain silk, which is more expensive and noticeable in its higher quality. The jacket can be single or double-breasted, with a single button in the centre.
• Trousers: Keep the trousers simple, in the same material as the jacket unless you've chosen a more outlandish jacket. The outer seams should be covered with a strip of the jacket's material, and they should sit slightly higher than regular business suit trousers. Opt for side adjusters over belt loops.
• Waist Covering: You can choose between a waistcoat or a cummerbund. A waistcoat can be finished in the same material as the lapels or the jacket, cut low and wide to display the shirt bib. A cummerbund wraps around the waist and should cover the trouser waistline entirely, made from the same material as the lapels with pleats facing upwards.
• Shirt: The shirt is unique to a tuxedo and essential to the look. It's always plain white with an extra panel of fabric sewn onto the front, either pleated or starched with a dimpled pattern. Studs are preferred over buttons, and if buttons are used, they should be covered and made of mother-of-pearl. The collar should be a simple fused turndown collar, never a button-down collar. French cuffs are preferable, and cufflinks should match the shirt studs.
• Accessories: Accessories should be done with restraint. Cufflinks and studs can be classic and elegant, like silver or gold with onyx. Suspenders, or braces, attach to the trouser waist and remain hidden under the jacket. The pocket square should be plain white and preferably silk. If wearing a flower in the lapel, opt for a single white or red blossom. A watch is optional, but a simple wristwatch with a black leather band is suitable.

Frequently asked questions