Creative Ways To Pop The Best Man Question

Asking your closest friends to be a part of your wedding is a significant and memorable moment. While there is no hard-and-fast rule about how to ask someone to be your best man, it is generally considered a special occasion that warrants more than a simple text message. Whether you decide to keep it simple or go all out with a personalised proposal box, asking your friends to be part of your big day is about more than the gift—it’s about the shared memories and excitement as you all embark on this important chapter together.

Plan an activity

Planning an activity is a great way to ask your best friend to be your best man. Here are some ideas to get you started:

Golfing or Baseball buddies

If you and your future best man are golf or baseball enthusiasts, why not ask him to join you for a round of golf or a baseball game? You could even treat him to a hot dog and a beer, and then pop the question. Alternatively, you could plan a more elaborate outing, such as a day at the links or slopes, or even a "bromantic" pre-wedding bike trip.

Sports fans

If you and your friend are fans of a particular sports team, you could invite him over to watch a game and ask him during halftime. Alternatively, you could secure tickets to see your favourite team play and pop the question then.

Whisky or beer lovers

If your friend enjoys whisky or beer, you could present him with a bottle of his favourite drink, perhaps even with a personalised label asking him to be your best man. You could also give him a set of custom golf balls or a personalised whisky glass.

Foodies

If your friend is a foodie, you could put together a snack box of seasonal favourites, guilty pleasures, or snacks that bring back great memories. For example, if you attended an epic game together, create a ballpark-themed snack box with popcorn, beer, soda, and boxes of candy. Alternatively, you could take him out for a meal at his favourite restaurant and pop the question over dessert.

Gamers

For the friend who loves gaming, you could pay homage to your shared hobby by planning a gaming session and presenting him with a custom controller or a set of printed guitar picks.

Remember, when asking your friend to be your best man, it's important to consider the nature of your relationship and choose an activity that represents a solid aspect of your bond. This will make your proposal more meaningful and memorable.

Send a card

Sending a card is a great way to ask someone to be your best man. It can be a good option if you're not great with emotional conversations or if you're worried about getting your words out in person.

There are plenty of different approaches you can take when sending a "will you be my best man?" card. You can use the card as an opportunity to express why the person is so meaningful to you and why you want them by your side on your wedding day. You can take a nostalgic route and use the card to highlight your favourite memories before popping the question. Or, if you don't want to get too sentimental, you can inject the card with humour or keep it super simple and just ask them in a straightforward way.

• Scratchcard: Add your best man's name and choose a balloon design to put his mark on it.
• Chalkboard card: This card from Norma & Dorothy has a textured finish and a brown envelope for a more formal feel.
• Calligraphy card: An affordable yet elegant option, you can tailor the script and envelope colour to match your wedding theme.
• Top Job Best Man Card: This card from Joanne Hawker conveys exactly what your best man means to you.
• Secret message card: Why limit your best man to one envelope-opening experience? This card from Here's To Us provides two opportunities for excitement.
• Contemporary hand-lettered card: If your best man is a straightforward guy, he'll love this elegant, hand-lettered card from Too Wordy.
• The Gentleman Notecards: Fancy yet understated, this set from Papier allows you to tailor your message by hand and includes enough notecards to send to other groomsmen and colleagues.
• "You'd Rock It In a Suit" Card: A tongue-in-cheek option from Wordplay Designs that's sure to bring a smile to your best man's face.
• "Simply The Best" Card: Serenade your best man with this Tina Turner-inspired card from Poppy's Papercuts at Papier.

Remember, you can make the card as personal as you like, and it can be a wonderful keepsake for your best man to remember the occasion by.

Give a gift

Giving a gift is a thoughtful way to ask someone to be your best man. It's a tangible token of your friendship and a memento of the occasion. Here are some ideas for how to pop the question with a present:

For the Sentimental Bestie:

Craft a personalised gift box filled with items that hold meaning for your friendship. Include a handwritten note expressing your gratitude for their presence in your life and asking them to be your best man. The box could contain a custom-made keyring with a photo of you both, a funny mug that references an inside joke, or a bottle of their favourite drink. You could even add a fun pair of novelty best man socks!

For the Tipple-Loving Mate:

Ask the question with a special bottle of his favourite spirit or a case of craft beer. You could attach a label that says "Will you be my best man?" or simply have a conversation as he opens the gift, expressing your desire for him to be your best man and sharing a drink together. It's a great way to make the moment memorable and enjoyable.

For the Dapper Gentleman:

Treat your pal to a stylish gift, such as a sleek hip flask, a sophisticated watch, or a pair of cufflinks. Engrave the item with his initials or a meaningful message, including your request for him to be your best man. It adds a personal touch and makes the gift even more special.

For the Adventure-Seeker:

If your friend is an outdoorsy type, consider gifting an experience you can share together, like a day of paintballing, go-karting, or even skydiving. As you embark on the adventure, ask him to be your best man, creating an unforgettable memory. Alternatively, you could gift him a cool multi-tool or a high-quality waterproof jacket, perfect for your next outdoor excursion.

For the Foodie Fellow:

Indulge his taste buds with a gourmet gift hamper filled with delicious treats. It could include artisanal cheeses, exotic spices, or small-batch chocolates. As he savours the delights, ask him to be part of your wedding party. You could even offer a food-based experience, like a cooking class or a gourmet dinner, to share a tasty adventure together.

Remember, the gift itself is a token of your appreciation, and the true honour lies in being chosen as your best man. So, have fun with the gift-giving and make it a special moment between friends!

Ask in person

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. Here are some ideas for how to ask your friend to be your best man in person:

Plan Around a Shared Activity

Consider asking your friend to be your best man while engaging in a shared hobby or activity. For example, if you and your friend enjoy golfing together, you could ask while enjoying a round of golf. Or, if you both support the same football team, you could invite them over to watch a game and pop the question during halftime. Asking your friend to be your best man while participating in a shared activity can make the moment more personal and meaningful.

Lead the Conversation to the Topic

If you're unsure how to bring up the topic, try leading the conversation towards your relationship and how much you appreciate your friend. Let them know that you've found the right person and that you would be honoured if they stood by your side as your best man. This approach can help ease into the question and make it feel more natural.

Make it a Special Occasion

Consider making the occasion extra special by incorporating a gift or a favourite activity. For example, you could treat your friend to a nice dinner or a round of golf before popping the question. Alternatively, you could give them a small gift, such as a bottle of their favourite liquor, a personalised mug, or a best man card. These touches can add to the significance of the moment and show your friend how much you value their presence in your wedding.

Keep it Simple

While you may want to make a grand gesture, sometimes a simple approach is best. Ultimately, your friend will be thrilled to be asked to be your best man, regardless of how you ask. A straightforward question, such as "Will you be my best man?" can be just as effective as a elaborate proposal. Remember, the most important thing is to let your friend know how much you value their friendship and support on your big day.

Make it funny

Asking someone to be your best man is a big deal, but that doesn't mean you can't have some fun with it! Here are some ideas for injecting some humour into your proposal:

Use a Card

If you're not great with emotional conversations, you could use a card to do the talking for you. You could go down the nostalgic route and fill the card with your favourite memories, or keep it light and funny with an inside joke. You could even send a funny one-liner card with a serious message at the end.

Get a Gift

A gift is a great way to ask someone to be your best man, and there are plenty of options to add a humorous twist. You could get them a personalised whisky glass with an empty glass design, a pair of face mash socks, or a t-shirt with a funny message. If your friend enjoys a drink, you could get them a miniature bottle of Jack Daniel's with a yes/no answer label, or a beer with their face on it.

Plan an Activity

If you and your friend share a hobby, you could plan an activity and pop the question during it. For example, if you're both golfers, you could switch their golf ball with a personalised one that asks the question. Or, if they're a football fan, you could get them a personalised football shirt with a proposal message.

Get Them a Treat

Everyone loves a sweet treat, so why not get them a chocolate bar with a personalised wrapper asking the question? Or, if they're more of a whisky fan, you could get them a bottle of their favourite whisky with a customised label.

Send a Balloon

A fun and quirky way to ask your friend to be your best man is to send them a "pop me" balloon with a proposal message inside. It's a unique way to surprise them and get a definite answer!

So, there you have it! Some fun and humorous ways to ask your friend to be your best man. Good luck with your proposal!

Frequently asked questions