Asking Your Son 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. So, how do you ask? Well, it's a good idea to consider the person you're asking, their availability, and what you expect from them. You could plan your proposal around your favourite shared activity, or send a card if you're not great with emotional conversations. Gifts are also a popular option, from personalised t-shirts to whiskey glasses. But remember, you don't need a grand gesture – a simple, heartfelt question will do!

Plan around a shared activity

If you and your son have a history of enjoying certain hobbies, pastimes, or activities together, you can use these as a great backdrop for asking him to be your best man. Here are some ideas for planning around a shared activity:

Sports

If you and your son bond over sports, you can plan a day out doing a sports-related activity that has a special meaning for both of you. For example, you can go golfing, visit the driving range, or play paintball or pickleball. If your son is a fan of a particular sport or follows a specific team or individual, you can also attend a sports event together.

Outdoor Adventures

Outdoor activities are a popular choice for father-son bonding. You can go hiking, camping, or explore nature together. This provides an opportunity for deeper conversations and shared experiences while also teaching important skills like fire lighting, tracking animals, and navigating your environment.

Amusement Parks

Amusement parks or theme parks offer an exciting day out, with adrenaline-fuelled rides and fun activities. This can be a great way to create memorable experiences and spend quality time together.

Cooking or Baking

Cooking or baking together can be a fun way to teach your son some basic kitchen skills and share your signature recipes. It's also an opportunity to try out new recipes or bake some family favourites.

Board Games and Puzzles

A good old-fashioned board game or puzzle can bring back nostalgia and provide a relaxing evening at home. You can try classic options or explore new releases, including legacy games that change each time you play.

Remember, the key is to choose an activity that you and your son enjoy doing together and that allows for conversation and connection. This will make your request for him to be your best man even more meaningful and memorable.

Ask in person

Asking your son to be your best man is a big deal, and it's natural to want to make it a special moment for the both of you. Here are some ideas for how to ask your son to be your best man in person:

Plan a special outing

Create a meaningful memory by planning a special outing with your son. This could be an activity that you both enjoy, such as golfing, hiking, or watching a football game. During the outing, find the right moment to pop the question. For example, if you're watching a football game, you could ask during halftime. This approach combines the special moment of asking your son to be your best man with a shared interest, making it more personal and memorable.

Make it a sentimental moment

If you want to go beyond a simple question and create a more sentimental moment, consider pairing your request with a meaningful gift or card. For example, you could give him a gift box with items related to your wedding or your relationship. This could include items such as a tie, cufflinks, or a personalised item with his initials or the words "best man." You could also include a handwritten note or card expressing your feelings and asking him to be your best man. This adds a thoughtful touch to your request.

Keep it casual

If your son is more laid-back or introverted, you might want to ask him casually during a regular conversation or hangout session. This approach is straightforward and respects his personality. You could say something like, "So, we've got a wedding coming up...wanna be in it?" This approach is especially suitable if your son is shy or prefers not to be the centre of attention.

Make it a celebration

If your son enjoys celebrations and attention, you can make a bigger deal out of asking him to be your best man. Plan a special dinner or get-together just for the two of you, creating a memorable occasion. During the dinner, pop the question and perhaps offer him a drink or a small gift to mark the occasion. This approach recognises his personality and makes it a fun and exciting moment for both of you.

Remember, the most important thing is to consider your son's personality and what would make the moment meaningful for the two of you. Whether you keep it casual or make it a grand gesture, he will surely be honoured and thrilled to be asked to stand by your side on your big day.

Send a card

If you're not great with emotional conversations, you might want to ask your son to be your best man through a card. You can take a few different approaches when sending a "will you be my best man?" card.

One option is to use the card to express how meaningful your son is to you and why you want him to be your best man. This is a great opportunity to let him know how much he means to you and how important his role will be on your big day.

Another idea is to take a nostalgic route and use the card to highlight your favourite memories together. This can be a wonderful way to remind him of the special moments you've shared and how much your relationship means to you.

If you don't want to get too emotional, you can always infuse the card with humour or keep it simple and straightforward. A funny card can be a great icebreaker and can make the moment more lighthearted.

Whatever approach you choose, sending a card is a thoughtful way to pop the question and will surely make your son feel loved and appreciated. It will also serve as a wonderful keepsake that he can treasure for years to come.

• Scratchcard: Add your son's name and choose a balloon in his favourite colour to make it more personalised.
• Illustrated card: Opt for a simple yet meaningful card that can be tailored with details about your son and a printed message inside.
• Chalkboard card: Go for a textured card with a brown envelope for a more formal feel.
• Calligraphy card: Choose an affordable yet elegant card and tailor the script and envelope colour to match your wedding theme.
• Secret message card: Why limit yourself to one envelope? Go for a card with two envelopes to prolong the excitement and build anticipation.
• Contemporary hand-lettered card: If your son is a straightforward guy, a card with elegant hand lettering will surely impress him.
• Funny card: Send a lighthearted card with a tongue-in-cheek message that will bring a smile to your son's face.

Remember, the card you choose should reflect your relationship with your son and match the overall style and tone of your wedding.

Give a gift

If you're looking for a way to ask your son to be your best man, why not give him a gift and let the gift do the asking for you?

There are plenty of proposal gifts out there that can be used to pop the question. From personalised t-shirts to golf balls, whiskey glasses, and even baseballs, there's sure to be something that your son will not only use but also love.

If you share a favourite sport or activity, you could give him a gift related to that. For example, if you're both golf enthusiasts, you could give him a set of personalised golf balls or a golf ball marker. Or, if he's a baseball fan, you could gift him a baseball with his name and wedding title on it. If he's into football, you could give him a football-shaped pen or a mini football helmet.

If you and your son enjoy a particular drink together, you could give him a bottle of his favourite spirit or a case of beer with a personalised label asking him to be your best man. You could also get him a personalised hip flask, whiskey glass, or beer mug. If he's more of a wine drinker, you could give him a bottle of his favourite vintage with a custom label or a personalised wine glass.

For a more general gift, you could give him a personalised pocket watch, wallet, or set of cufflinks. You could also get him a funny t-shirt or a pair of novelty socks. If he's into gadgets, you could give him a credit card-sized bottle opener or a wireless charging desk caddy.

Whatever gift you choose, you can make it even more special by including a handwritten note or card asking him to be your best man. This will not only make the moment more personal but also give him a keepsake to remember the occasion by.

Ask directly

If you want to ask your son to be your best man, you could always just ask him directly. While it may seem obvious, it's important to remember that your son will likely care more about the fact that you asked him to be your best man than how you asked him.

However, if you want to make the moment more special, you could consider incorporating a hobby or activity that you and your son enjoy doing together. For example, if you both love golfing, you could ask him while you're out on the golf course. Alternatively, if you're both fans of the same football team, you could invite him over to watch a game and pop the question during halftime.

If you're not sure how to bring it up in conversation, you could always write your son a card. This can be a great way to express how much your son means to you and why you want him to be your best man. You can also include a handwritten note inside the card, asking him to be your best man.

Frequently asked questions