Asking Your Best Man: Making The Wedding Request

Asking someone to be your best man is a big deal. It's a huge honour and a privilege, so it's important to ask in a memorable way. 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. So, how do you go about asking?

Well, there are endless creative ways to pop the question. You could plan around your favourite shared activity, whether that's playing golf or watching a football game together. You could give them a gift, such as a personalised print, a hip flask, a card, a six-pack of beer, or a pair of socks. Or, you could simply ask in person – no frills, no fuss.

Creative ways to ask

Asking someone to be your best man is a big deal, so you'll want to make it memorable. Here are some creative ways to ask that special person to be your right-hand man:

Plan Around a Shared Activity

Think about hobbies and pastimes you and your best man-to-be enjoy together. Asking during one of these activities can make your proposal more personal and meaningful. For example, if you've been golfing buddies for years, pop the question during a round of golf. Or, if you're both fans of the same football team, invite them over to watch a game and ask during halftime.

Send a Card

If you're not great with emotional conversations, you can express your feelings through a card. You can go down the nostalgic route and highlight your favourite memories, or keep it simple and straightforward. Cards are also a great keepsake for your best man to remember the occasion.

Give a Gift

There are many "proposal" gifts available, such as personalised t-shirts, golf balls, or whiskey glasses. Or, give them something they'll use, like a personalised coffee mug if they're a coffee lover, or a wine glass if you've shared a wine-tasting trip together.

Handwritten Note

A heartfelt, personal letter is a timeless way to ask someone to be your best man. Reflect on your friendship and share why having them by your side on your wedding day matters to you.

Surprise Dinner or Drinks

Gather your groomsmen for a dinner or drinks and pop the question to the whole group. It's a great way to celebrate the moment together and will make for a fun and memorable evening.

Sports or Game Day

If your group is into sports, consider asking them during a game. You can even make it more special by wearing personalised shirts or caps that say "Groomsman" or "Best Man."

Choosing the right person

Consider your closest friends

Think about your group of friends and who you are closest to. If you have a large group of friends or are part of multiple friendship circles, it might be tricky to choose just one person. In that case, consider your long-standing friendships and ask yourself who has been there for you through thick and thin. Out of all your friends, who is the first person you text in a crisis? Who do you most enjoy spending time with? Being honest with yourself during this thought process should make the decision easier.

Think about timing

If you and your partner are planning a long engagement, there's no rush to choose your best man. Friendships can shift over time, so it's generally better to wait and see. Ideally, you should let your best man know about a year before the wedding to give them plenty of time to plan the stag party.

Evaluate their ability to handle the responsibilities

The best man has several important responsibilities, including planning the stag party, taking care of the rings, and making a speech. Therefore, it's crucial to choose someone who you can trust to be reliable and handle these tasks.

Consider a best woman

If you don't have many male friends or are struggling to choose between your male friends, remember that weddings are becoming less traditional. You could consider asking a female friend or cousin to be your "best person" if that feels right for you. Just make sure to get the blessing of your partner first!

Forget about obligation

You don't have to choose your brother or cousin as your best man just because you feel obligated to do so. Similarly, if you were someone else's best man, that doesn't mean they have to return the favour. While it's important to be considerate and not offend anyone, ultimately, it's your day, and you should choose someone who you truly want by your side.

Planning around a shared activity

Planning a proposal around a shared activity is a great way to make asking your best man more personal. It's a good idea to choose an activity that has a special meaning for the two of you. For example, if you and your best man-to-be are both avid golfers, you could ask them while enjoying a round of golf. Alternatively, if there's a football team you're both obsessed with, you could invite them over to watch a game and pop the question during halftime.

If you're planning a destination wedding, you could propose to your best man during a trip to the location. This way, you can combine the proposal with a fun activity and give them a chance to get acquainted with the area. For instance, you could plan a day of skiing or a visit to a local brewery.

If your best man lives far away, you could send them a proposal gift box with items related to the shared activity. For example, if you both enjoy coffee, you could include a personalised mug and a bag of beans from a local roaster. Or, if you share a love of golf, you could send them a set of custom golf balls with a pun, like "Are you ready to PAR-TEE as my best man?".

When planning a proposal around a shared activity, it's important to consider the other person's availability and whether they have the time and energy to devote to your wedding planning. It's also a good idea to provide them with your wedding date and location when you ask them to participate.

Asking through a card

Asking your best mate to be your best man can be nerve-racking, but it's important to make it memorable. If you're not great with emotional conversations, you can ask your best man through a card. Here are some ideas to make your card stand out:

The Sentimental Card

Use the card as an opportunity to express how meaningful the person is to you and why you want them by your side on your wedding day. Dive into your favourite memories together and highlight why you value your friendship. This approach will make your friend feel appreciated and loved.

The Nostalgic Card

Take a trip down memory lane and use the card to reminisce about your favourite moments together. Recall inside jokes, funny stories, and adventures you've shared. This card will evoke happy memories and create a warm, fuzzy feeling.

The Humorous Card

If you and your friend share a great sense of humour, lean into it! Create a card filled with inside jokes, funny one-liners, or references that only the two of you will understand. You can even include a humorous letter, pretending to be assigning them a top-secret mission as your "best man agent".

The Simple Card

Sometimes, less is more. A straightforward and simple card can be just as impactful. A card with a clear and concise message, such as "Will you be my best man?" can be elegant and effective. You can even tailor the card to match your wedding theme colours.

The Creative Card

Get creative with your card design! Consider a scratch-off card, where your friend can scratch to reveal the hidden question. Or, opt for a card with a funny pun, an alcohol-themed illustration, or a gaming reference if your friend is a gamer. You can also include a small gift, like a pair of personalised socks or a mini bottle of their favourite liquor, to accompany the card.

Remember, the card is a great way to showcase your personality and your relationship with your friend. Make it heartfelt, fun, or creative—whatever suits your style! Good luck with your best man proposal!

Asking with a gift

Asking your best friend to be your best man is a nerve-racking task, but there are many ways to do it. One way is to give them a gift, and there are plenty of options to choose from. Here are some ideas for asking with a gift:

Gifts with a Personal Touch

Customized gifts are a great way to show your friend how much you value your friendship. You could get them a proposal box set, or something engraved or personalized with their initials, like a hip flask, cufflinks, or a watch. If you share a hobby, you could get them something related to that—for example, if you're both golfers, you could get them a set of custom golf balls. Or, if you're whiskey drinkers, you could get them a personalized whiskey glass or decanter. You could even get creative and engrave their invitation on their favourite bottle of alcohol.

Gifts to Make Them Laugh

If you and your friend share a silly sense of humour, you could get them a novelty gift, like a t-shirt or hoodie with a tuxedo printed on it. Or, if they're always running late, you could get them a set of clock cufflinks to remind them to be on time for your big day.

Gifts to Share an Experience

If you're not sure what gift to get, you could always share an experience with your friend. You could go for a round of golf, or to a sports game, or out for a fancy dinner, and pop the question while you're there. Or, if you want to give them something they can keep, you could give them a book related to a shared interest, like a book of modern speeches, or a book of bike rides if you're a keen cyclist.

Gifts to Get Them Excited

If you want to get your friend excited about the wedding, you could give them a gift that hints at what's to come. You could get them a book of best man jokes, or a book of tie knots if you've already chosen a style for them to wear. You could even give them a starter kit with some essentials, like cufflinks, a bow tie, and a small bottle of their favourite drink.

Gifts to Keep it Simple

If all else fails, you can always keep it simple. 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 could include a funny illustration, or a photo of the two of you, or a heartfelt message about your friendship.

Remember, the most important thing is to make your friend feel appreciated and excited about your wedding. Good luck!

Frequently asked questions