Asking Your Best Mate To Be Your Best Man

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. 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. While there's no strict etiquette on how to ask, it's generally recommended to do it in person. Here are some creative ways to pop the question to your best mate:

- Plan an activity you both enjoy, such as golfing or watching a football game, and ask during the activity.

- Send a thoughtful card, either a simple invitation or a nostalgic letter highlighting your favourite memories.

- Give a gift, such as a personalised whisky glass, a book, or a funny one-liner card.

- Go for a group outing with all your groomsmen and ask them at the same time.

- Ask during a double date with your fiancé and your groomsman-to-be's significant other.

Plan a group outing

Planning a group outing is a great way to ask your best man and groomsmen to be a part of your wedding. Here are some ideas on how to go about it:

Choose the Right People

If you have a massive group of friends, choosing your best man and groomsmen can be a challenging task. A good approach is to select individuals you have been friends with for a long time and who have been there for you throughout the years. Ask yourself, "Who do I text in a crisis?" or "Who do I most want to hang out with after a long week?" Answering these questions honestly will help you decide who to include in your wedding party.

Give Them a Heads-Up

If you and your partner are planning a long engagement, there's no need to rush into a decision. It's generally better to give your best man and groomsmen plenty of time to plan the stag or bachelor party, usually about a year before the wedding.

Ask Yourself, "Who Can Handle It?"

Keep in mind that the best man has several responsibilities, including planning the stag party, taking care of the rings, and making a speech. The groomsmen will also have tasks to manage, so choose individuals you can trust to be responsible on the day.

Consider a Best Woman

If you don't have many male friends or prefer a mixed-gender wedding party, you can always ask a female friend or cousin to stand by your side. It's your wedding, so feel free to bend the rules and choose the people who mean the most to you.

Forget About Obligation

You don't have to ask your brothers or cousins to be your best man or groomsmen just because you feel obligated. While it's important to be careful not to offend anyone, your wedding day is about you and the people you want to be there, celebrating with you.

Make a Fuss

Now comes the fun part—planning the group outing! While you might be tempted to send a text or give them a quick call, asking your best man and groomsmen to be part of your wedding is a special honour, so make it memorable. Here are some creative ways to pop the question:

• Engrave Their Invitation: Customise their favourite bottle of alcohol with an engraved invitation. You can also include personalised mugs or glasses for them to pour their drinks into.
• Subscription Box Surprise: Take advantage of the popularity of subscription boxes. Select a box that represents your friend or your relationship with them. Many subscription services offer free or inexpensive introductory offers, so you can try it out without a long-term commitment. Include a note in the box with a formal invitation.
• The Classic Cigar: A cigar symbolises the unique sense of brotherhood between good friends, making it a perfect groomsmen invitation. You can secure the cigar to a piece of quality stationery or an envelope with a letter inside, asking them to be a part of your special day.
• Cufflink Clues: Wedding attire for men can be monotonous, so add some flair by giving your prospective groomsmen custom cufflinks. Include a short message, their initials, or a phrase unique to each person. They'll have to open the box to find out what's inside, and you can ask them to be your groomsmen when they do!
• Comedy Cards: If your friends appreciate a good joke, create proposal cards full of inside jokes that will have them roaring with laughter. At the end of the cards, include a humorous letter noting that they have an important assignment, with pictures of fingerprints at the bottom and space for them to sign.
• Get Everyone Together: Invite all your prospective groomsmen to an event, like lunch, drinks at a pub, or a weekend hangout. Make it informal or formal, whatever suits your style. Choose an event or location that commemorates your friendship or represents a milestone in their lives.
• Starter Kit Surprise: Put together a starter pack with essentials like cufflinks, a bow tie or printed tie, and a small bottle of their favourite drink. Present it to them as a random gift, and then pop the question when they open it.
• Tie Tutorial: Create an educational booklet on ties and different knot techniques. Give it to your friends, telling them you're excited to see how good (or bad) their tie knots are at your wedding. They'll quickly catch on to your groomsmen invitation idea!
• Tailor-Made Invitation: Print out a screenshot of a tailor or tuxedo rental service in your friends' area. On the back, write a personal story, noting how excited you would be if they accepted your invitation to be a groomsman. It's an informal and funny way to ask!
• Go Over the Top: You can also go over the top with your invitation. Embarrass your friends by sending them flowers with official invites or asking them in private while passing around roses. Create an awkward yet joyous moment they won't forget!
• Boozy Bouquet: Instead of flowers, get them a bouquet of liquor. Miniature bottles suspended on sticks inside a vase or pot look just like flowers but are much more fun and useful. Include a note asking them to be your groomsmen, and you'll be all set!
• Keep It Simple: If you're a man of few words or your prospective groomsman lives far away, a simple invitation card will do the trick. Write a personalised message or just include your name, making it clear that you want them to be part of your wedding party.

Remember, the key is to make your best man and groomsmen feel special and honoured to be a part of your wedding. Choose an invitation idea that suits your style and the dynamic of your friendship, and have fun with it!

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. There are several ways you can go about this:

Dive into why they're meaningful to you

You can use the card as an opportunity to express how much this person means to you and why you want them by your side on your big day. This is a great way to make your request feel more personal and heartfelt.

Take a nostalgic route

Use the card to reminisce about your favourite memories together. This will not only make your friend feel special but will also bring back fond memories, strengthening your bond.

Keep it light with humour

If you don't want to get too emotional, you can add a touch of humour to your card. This could be through inside jokes or funny one-liners. It's a great way to keep the tone light and fun while still conveying your request.

Keep it simple and straightforward

If you're not one for many words, a simple and direct approach can also work well. A straightforward "Will you be my best man?" will get your message across clearly and effectively.

Make it a keepsake

No matter which approach you choose, consider adding a personal touch to your card, such as a handwritten note or illustration. This will make it a cherished keepsake for your best man-to-be, reminding them of this special occasion.

Remember, the most important thing is to convey your appreciation and the honour you feel in having them by your side as your best man.

Give a gift

Giving a gift is a great way to ask someone to be your best man. It can be a fun and memorable way to pop the question and makes your friend feel special. Here are some gift ideas to help you ask that all-important question, "Will you be my best man?"

Customized Gifts

Customized gifts are a fantastic way to show your friend that you want them by your side on your big day. You can get creative and choose items that reflect their personality and your relationship. For example, if your friend is a golfer, you could get them a set of personalized golf balls. If they're into fashion, a stylish monogrammed handkerchief or a tie with a fun print might be a perfect choice. You could also opt for engraved cufflinks, a personalized hip flask, or a custom illustration of the two of you.

Experience Gifts

If you and your friend share a love for a particular activity, why not make your proposal part of that experience? Plan a day at the golf course, a gourmet dinner, or even a simple coffee catch-up, and pop the question during your favourite shared pastime. This adds a personal touch to your proposal and creates a memorable experience for both of you.

Gift Boxes

Curating a gift box is an excellent way to ask your friend to be your best man. You can fill it with a variety of items, from funny best man notebooks to their favourite bottle of liquor, custom-engraved glasses, or even a book on how to make the perfect knot for their tie. You can also include a handwritten note expressing your sentiments and asking the big question.

Sentimental Gifts

Sometimes, the best gifts are the ones that come from the heart. If you and your friend share a lot of memories, a sentimental gift might be the perfect choice. You could give them a framed photo of the two of you or a personalized print that celebrates your friendship. A gift like this will not only make them feel special but also remind them of the good times you've shared.

Remember, when choosing a gift, consider your friend's personality and interests. Make it personal, and don't be afraid to add a touch of humour if that's something you share. Good luck with your proposal!

Plan around a shared activity

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

Plan a Special Outing

Treat your friend to a day out doing a shared activity that holds special meaning for both of you. This could be golfing, skiing, paintball, pickleball, or even watching your favourite sports team play. During the outing, pop the question and ask your friend to be your best man. This approach adds a unique and memorable twist to your proposal.

Host a "Man Meal"

If you have multiple friends you want to ask to be groomsmen, plan a "man meal" and gather all the guys together at a favourite restaurant. You can then ask them all to be part of your wedding party at the same time. This approach fosters camaraderie and makes the occasion more festive.

Go on a Hike or Coffee Date

If you prefer a more intimate setting, set up a one-on-one hang session with your friend. Go on a hike, grab coffee, or meet for lunch. Focus the conversation on your relationship and how much you appreciate your friend. Then, pop the question and ask your friend to be your best man. This approach is simple yet meaningful.

Gift a Book or Magazine Subscription

If your friend is an avid reader or enjoys a specific hobby, consider gifting a book or magazine subscription related to their interests. For example, if your friend is a cyclist, gift them a book like "Lonely Planet's Epic Bike Rides of The World". Slip in a handwritten note inside the book, asking your friend to be your best man. This approach is thoughtful and unexpected.

Plan a Weekend Getaway

For a more elaborate gesture, plan a weekend getaway with your friend, such as a "bromantic" pre-wedding bike trip or a camping trip. During the trip, ask your friend to be your best man. This approach allows for quality time together and creates a memorable backdrop for your proposal.

Ask in person

Asking someone to be your best man is a big deal, so it's important to put some thought into how you'll do it. Here are some ideas for asking in person:

Plan Around a Shared Activity

If you and your best man-to-be share a hobby or favourite activity, consider incorporating that into your proposal. For example, if you regularly play golf together, ask him while you're out on the course, or if you're both fans of the same football team, invite him over to watch a game and pop the question at halftime. This is a great way to make your request feel more personal and meaningful.

Go for a One-on-One Hangout

If you want to make the moment more intimate and special, set up a one-on-one hangout session with your friend. This could be something as simple as grabbing a coffee or going for a hike—whatever activity you usually enjoy doing together. During your hangout, you can ask your friend to be your best man and even treat him to a small gift or a round of drinks to mark the occasion.

Take Them Out for a Meal

Another way to ask your friend to be your best man is to take them out for a meal, either just the two of you or with your partner and their partner, if applicable. You can pop the question over dinner or give them a gift with an invitation to be your best man. This is a more formal way to ask and allows you to celebrate the occasion with good food and company.

Make It a Casual Conversation

If you're not one for grand gestures, you can simply ask your friend to be your best man the next time you hang out. Bring it up in casual conversation or ask them while you're out doing an activity together. This low-key approach takes the pressure off and still conveys the same message.

Remember, the most important thing is to choose an approach that feels comfortable and authentic to you and your relationship. Good luck with your best man proposal!

Frequently asked questions