Popping The Question: Asking Your Best Man And Ushers

Asking your friends to be ushers or best men at your wedding is a significant and memorable moment. Your best men and ushers will be by your side throughout your wedding journey, supporting you and sharing in the excitement. But how do you go about asking them? Should you give gifts, and how many people should you ask?

There's no hard rule about the number of ushers or best men you should ask—it depends on the size of your wedding and your personal relationships. It's important to choose the people who mean the most to you, whether that's your brother, best friends, college mates, or close colleagues. Asking your friends to be part of your wedding party is an opportunity to show them how much they mean to you. Make it fun, thoughtful, and personal.

Asking in-person

Asking your friends to be ushers or groomsmen is an opportunity to show them how much they mean to you. Here are some ideas for asking them in person:

Ask them over dinner or drinks

Gather your chosen groomsmen and ushers for a celebratory dinner or drinks, then pop the question to the whole group. This is a great way to celebrate the moment together and will allow them to get to know each other before the wedding.

Ask them during a shared hobby or activity

If you and your friend share a hobby, like golfing, fishing, or video gaming, consider asking them while you're doing that activity. For example, you could ask while on the golf course or at a baseball game. You could even treat them to a hot dog and a beer, and then pop the question.

Ask them at a special event

If you're planning on having an engagement party, this could be a great opportunity to ask your ushers and groomsmen in person. You could also ask them at another special event, like a birthday party or holiday celebration.

Keep it simple and direct

Ultimately, guys don't need a lot of fanfare when it comes to this type of proposal. A simple, direct question like, "Will you be my usher?" or "I'd really love for you to be an usher at my wedding. What do you think?" is often enough. You can also call them on the phone to ask, or even ask them in person while hanging out casually.

Remember, asking someone to be your usher or groomsman is a sign of respect, friendship, and fidelity, so make sure to choose people who you have long-lasting bonds with and who will support you throughout the wedding planning process.

Asking during a shared activity

Asking your friends to be ushers during a shared activity is a great way to make your proposal feel more personal. It's a good idea to plan your proposal around your favourite shared activity. For example, if you and your friend have been golfing together for years, why not ask them to be your usher while you're enjoying a round of golf? Or, if you're both big fans of a particular football team, invite them over to watch a game and pop the question at half-time.

If you're not sure how to bring it up in conversation, you could consider giving them a gift that does the asking for you. There are plenty of "proposal" gifts available, from personalised t-shirts to golf balls and whiskey glasses, or you could give them a card. If you're not sure what to write, you could use the card as an opportunity to tell them how much they mean to you and why you want them to be your usher.

If you're asking multiple people to be ushers, you could gather them all together for a dinner or drinks and then pop the question to the whole group. This is a great way to celebrate the moment together.

Asking over the phone

Asking your best man and ushers to be part of your wedding party is an opportunity to show them how much they mean to you. While it is traditionally done in person, you can still make it fun, thoughtful, and personal over the phone. Here are some ideas to make your proposal memorable:

Creative Ways to Ask Over the Phone

• Handwritten Notes: Send a heartfelt, personal letter to your best man and ushers. Reflect on your friendship and share why having them as part of your special day matters. You can even include a gift or a card with your letter.
• Surprise Drinks Over the Phone: Plan a virtual get-together with your best man and ushers. Prepare some drinks and pop the question to the whole group over a video call. It's a great way to celebrate the moment together, even if you're not physically together.
• Sports or Game Day: If your group is into sports, consider asking them during a game. You can even send them personalised shirts or caps that say "Groomsman" or "Best Man" before the call to give them a hint.
• Proposal Gift: Send your best man and ushers a proposal gift box with items like ties, socks, cufflinks, engraved flasks, or even a book on speech ideas. You can also include a handwritten note asking them to be a part of your wedding party.
• The 'Will You Be My Best Man?' Chat: Keep it simple and direct. Give them a call and ask the question. While it may seem nerve-wracking, your closest friends will likely say yes, and you can make it a fun and light-hearted conversation.

Things to Consider:

• The Number of Groomsmen: There is no hard rule on the number of groomsmen you should have. It depends on the size of your wedding and your personal relationships. Generally, small weddings might have 2-3 groomsmen or just a best man, while larger weddings might include 5-7 or more.
• Gifts: While it's not required, giving your groomsmen a gift is a nice gesture to show your appreciation. It can be a meaningful keepsake of your wedding and a way to thank them for their time and effort.

Remember, asking your friends to be part of your wedding is about more than the gift or the proposal—it's about the shared memories and excitement as you embark on this important chapter of your life together.

Asking with a card

Creative Card Ideas

Add a creative twist to your proposal cards with these fun suggestions:

• Scratch-off cards—Add an element of excitement with a scratch-off card. Your groomsmen will have fun scratching to reveal the question, "Will You Be My Groomsman?".
• Mustache card—Send your groomsmen a card with a unique mustache on it, and they'll be curious and amused as they figure out your proposal.
• Great Party Open Bar Card—Let your groomsmen know what they need for the wedding—a great party with an open bar!
• Pokémon-themed card—For the gaming enthusiasts, a Pokémon-themed card with a Pokéball and the words "I Choose You" is a fun and creative way to propose.
• Meme proposal card—For the meme lovers, a proposal card featuring a popular meme is sure to bring a smile to their faces.

Stylish and Elegant Cards

If you're looking for a more elegant and understated approach, consider these stylish card ideas:

• Chalkboard card—A card on a chalkboard background adds a stylish and modern touch to your proposal. You can even add photos and text to make it extra special.
• Calligraphy card—An affordable yet elegant option is to choose a card with beautiful calligraphy. You can tailor the shade of the script and envelope to match your wedding theme.
• Secret message card—Add a little intrigue with a secret message card. Your groomsmen will have the pleasure of opening two envelopes, prolonging the excitement of your proposal.
• Minimalist proposal card—A chic and classic card with an uncoated matte finish is a simple yet sophisticated choice. It provides ample space to write a personalised message and won't smudge easily.
• Watercolour request card—A custom invitation with a watercolour design is a unique and elegant way to propose to your groomsmen. You can add photos and text to personalise it further.

Humorous Cards

Inject some humour into your proposals with these light-hearted card ideas:

• Suit Up cards—These cards feature a sleek bow-tie design and pair nicely with any bridesmaid cards and wedding theme ideas. They are a fun way to invite your guys to suit up and join your wedding celebration.
• "You'd Rock It In a Suit" card—A tongue-in-cheek card that will surely bring a smile to your groomsmen's faces. It's a playful way to propose and celebrate their role in your special day.
• Simply the Best Card—Serenade your groomsmen with a Tina Turner-themed card. After all, they are about to become the best men by your side!

Personalised Cards

Make your proposals extra special with these personalised card ideas:

• Will You Be My Usher? card—A cute, personalised card is a wonderful way to ask someone to be your usher. It can be tailored to the recipient, making them feel valued and honoured.
• Best Man Groomsman Usher Proposal Note Card—A proposal note card with a Kraft envelope is a fun and unique way to pop the question. It adds a touch of whimsy while conveying your heartfelt request.
• Groomsmen Draft Card—Propose to your groomsmen in style with a call to service. Send this card along with a bottle of your friend's favourite drink to make it even more special.
• Customised cards—Many card designs allow for customisation, such as adding names, roles, and even photos. You can also include personalised messages inside the cards to make them truly meaningful.

Asking with a gift

Gift Boxes

Curate a special box with a few smaller gifts inside. You can include items like a tie, socks, cufflinks, an engraved hip flask, a pocket knife, or a personalised note. These boxes can be tailored to each groomsman's interests and are a great way to add a surprise element to your proposal.

Drinks and Treats

Proposing with a bottle of their favourite drink or a selection of treats is a fun and budget-friendly option. You could include a nice bottle of single malt whisky, a selection of craft beer, or a bottle of wine. Pair it with some chocolates, truffles, or even a personalised cookie set for a sweet touch.

Accessories

Accessories like belts, wallets, or watches are useful gifts that can also be personalised. A handmade leather belt, an elegant wallet, or a unique watch with a tree of life design are all options that can be enjoyed long after the wedding.

Self-Care and Grooming

A self-care or grooming kit is a luxurious and practical gift. You could include a manicure set, a beard grooming kit, or a set of cologne or aftershave. These gifts will ensure your groomsmen are looking and feeling their best on the big day.

Experiences

Instead of a physical gift, you could treat your groomsmen to an experience you can enjoy together. Consider tickets to a sporting event, a whisky tasting set, or a weekend away. These shared experiences will create lasting memories and give you a chance to celebrate your friendship.

Remember, when asking your groomsmen to be by your side on your wedding day, it's the thought that counts. Whether you go for a simple gift or something more extravagant, your groomsmen will appreciate the gesture and the opportunity to share in your special day.

Frequently asked questions