Asking Your Wedding Entourage: Best Man And Groomsmen

Asking someone to be your best man or a groomsman is a big deal. It's a special role that comes with responsibilities and an important place in your big day. So, how do you go about popping the question to your best mate?

Well, there's no one right way to do it. You could plan a dramatic proposal or play it cool. You could ask in person, over a heartfelt conversation, or with a card or letter if you're not great with emotional conversations. You could give them a gift, like a flask, a custom-engraved item, or a bottle of whisky. Or you could simply ask with a text or phone call, especially if your potential groomsman lives far away.

Whatever you decide, the key is to make your groomsmen feel honoured and cherished.

Gifts: A thoughtful gift can be a great way to ask someone to be your best man or groomsman

Asking your best mates to be your best man and groomsmen is a nerve-racking task, but a thoughtful gift can make it easier. While gifts are not compulsory, they are a sweet way to honour your relationship and say "thank you" in advance. Here are some gift ideas to help you pop the question to your best man and groomsmen:

Gifts for the Sentimental Type

• A personalised print or card: Make your proposal cinematic with a movie-style art print or a colourful print with inside jokes.
• A monogrammed glass: For a subtle personal touch, engrave their initials on a cool gilded glass.
• A pocket watch: Gift them a stylish, art-deco engraved silver pocket watch, a classic symbol of tradition and sophistication.
• A photo frame: Put a photo of you both in a geometric frame before popping the question.
• A personalised hip flask: A quintessential groomsman gift, a bespoke hip flask will deliver some liquid courage for the big day.
• A book of modern speeches: Handing over this book might give the game away, but it will also help them prepare for their own speech.
• A telegram: Send your best man a custom-made telegram featuring vintage stamps for an old-school proposal.
• Cufflinks: Gift them sleek, monogrammed cufflinks that will go with every suit and be a lasting memento.
• A tie: If you've decided on your wedding suit, kit your best man out early with a matching tie.
• Socks: Select a pair of wedding socks and send them with a handwritten note.
• A credit card holder wallet: An elegant, personalised leather wallet will only get better with time.

Gifts for the Fun-Loving Type

• A funny card: If you're not usually sentimental, send a humorous proposal card that says "Will you be my best man?"
• A bottle of their favourite spirit: Display a personalised invitation on their favourite bottle of alcohol.
• A mail subscription box: Sign them up for a box of their favourite things as a trial, with a formal invitation included.
• A cigar: The cigar represents brotherhood, so secure a cigar to a piece of quality stationery with a letter inside asking them to accept.
• A bouquet of liquor: Instead of flowers, gift them miniature bottles of their favourite liquor arranged like a bouquet.
• A book on tie knots: For a light-hearted proposal, gift them a book on ties and different knots, telling them you're excited to see how good their tie knots are at the wedding.
• A funny one-liner book: Compile inside jokes or funny one-liners and add a humorous letter at the end, asking them to accept their "important assignment".
• A set of funny drinking gadgets: These will be a hit at the celebrations, and your groomsmen will be excited to try them out.
• A customised beer mug: Inspired by a traditional German stein, these mugs can be customised with names, titles, and logos, making for a unique keepsake.
• Customised koozies: These stainless steel can coolers are easily reusable and will keep their drinks cool.
• A poker set: For the gamer in your life, gift them a weather-proof poker set and invite them for a game night.
• A Cameo video message: If your best man lives far away, get their favourite celebrity to deliver your proposal via a personalised video message.
• A personalised coffee mug: Send the seller a photo of your best man and get a caricature printed on a mug. Include a bag of gourmet coffee for a non-alcoholic proposal.
• A novelty baseball: For the baseball fan in your life, a customised baseball with their new wedding title is a fun way to pop the question.
• Insulated travel tumblers: These stylish, personalised tumblers are perfect for drinking coffee or beer and can be customised with names and wedding roles.
• Etched windproof lighters: These useful, personalised lighters come in sleek colours and are perfect for a cigar lounge invitation.
• A personalised baseball bat: For the baseball lover, this Little League-approved bat is a thoughtful gift, especially if you've spent time on the field together.
• Groomsmen proposal socks: These socks say it all with the words "Will you stand as my groomsman?" printed on them.
• A tie and pocket square set: This stylish set is a perfect proposal box for the fashion-conscious groomsman.
• Monogrammed humidors: For the cigar enthusiast, an elegant humidor with their name, monogram, and wedding date is a unique gift.
• Stemless wine glasses: Treat your groomsman to a set of personalised wine tumblers and pop the question over a bottle of wine.
• A personalised football: Honour your unique friendship with a football printed with their name, wedding title, and wedding date.
• A fishing lure: This cool fishing lure can be personalised with the word "groomsman" and the wedding date, with space for a personal message on the back.
• A Swiss army knife: A thoughtful and useful gift, especially if your groomsman loves the outdoors.

Remember, you can also combine these gifts with creative ways to ask your best man and groomsmen, such as a casual hangout, a dinner, or a trip down memory lane.

In-Person: Asking in-person adds a personal touch and shows the importance of the question

Asking your best man and groomsmen to be a part of your wedding in person is a great way to add a personal touch and show how important the question is to you. Here are some ideas for how to do it:

Meet Up

Meeting up with your groomsmen-to-be is the most personal way to ask them to be part of your wedding. If you can't meet in person, consider using Skype, FaceTime, or a phone call to connect and share this moment. It's important to give them a heads-up and not leave it until the last minute—asking 6-8 months ahead of time is reasonable and will allow your groomsmen time to budget and plan any time off work.

Make It Uniquely You

When asking the question, share a moment that meant a lot to you, or thank them for supporting your relationship. For example, you could say something like, "I really appreciated it when you came and gave my car a jump at 2 AM when nobody else would answer their phone. It would mean a lot to have you in our wedding party. Will you be my groomsperson?"

Gift Them

Although it's not necessary to gift your groomsmen when you ask them, it can be a nice touch. Approach it as a token of your appreciation and friendship rather than a bribe. For example, if they know your friend’s usual Taco Bell order, a Blue Apron subscription might be a good mix of caring and useful. Alternatively, you could treat them to dinner when you ask.

Plan Around Your Favorite Activity

If you're asking someone to be your best man, chances are you have some hobbies or pastimes that you enjoy together. Asking them to be your best man while you're both enjoying these shared interests can make your request more personal. For example, if you've been golfing with your best man-to-be for years, ask them while you're out on the golf course.

Write a Card

If you're not great with emotional conversations, you could consider writing a card to your best man. You can use the card to dive into why the person is so meaningful to you, use it to highlight your favourite memories, or keep it simple and just ask them to be your best man in a straightforward way. Cards also make great keepsakes.

Cards: Cards are a simple, yet meaningful way to ask, especially if you're not great with emotional conversations

Cards are a simple and meaningful way to ask your friends to be your groomsmen, especially if you're not great with emotional conversations. You can make them lighthearted or sentimental, with playful sayings, classic designs, or modern aesthetics. They are also a great way to add a personal touch to your proposal.

• A simple, meaningful, illustrated card that can be tailored to your heart's desire, from the details of your groomsman to the printed message inside.
• A chalkboard card with brown envelopes for a more formal feel.
• An affordable yet expensive-looking calligraphy card, with the shade of the script and envelope tailored to your wedding theme.
• A card that looks like a best mate appraisal, conveying exactly what your best man means to you.
• A secret message card that prolongs the excitement, giving your friend two envelope-opening experiences.
• A contemporary hand-lettered card that stands out.
• A set of fancy yet understated notecards, with your 'will you be my best man?' message handwritten inside.
• A funny card with a tongue-in-cheek message, such as "You'd rock it in a suit".
• A card featuring a Tina Turner song, such as "Simply the Best".

You can also include cards as part of a groomsmen proposal gift, such as a box of their favourite items, a book, or a personalised item.

Timing: It's important to ask at the right time; not too early, but also not too late

Timing is everything when it comes to asking your best man and groomsmen. While it's important to give your friends enough notice, you don't want to spring it on them too early either. Here are some tips to help you find the right timing:

Give Them Enough Notice: Asking your wedding party to be part of your special day takes careful planning. You'll want to give your best man and groomsmen enough notice to ensure they can plan and prepare for the event. They may need to request time off from work, arrange travel, or make other accommodations. It's generally a good idea to pop the question at least six months to a year before the wedding. This gives everyone plenty of time to get organised without feeling rushed.

Not Too Early: While giving advance notice is important, you also don't want to ask too early. Asking a year or more in advance may be a bit premature. People's circumstances can change a lot in that time, and you want to be mindful of that. It's a delicate balance, but try to give them enough time without making it overly early.

Consider Key Milestones: When deciding on the timing, consider other milestones in your wedding planning. For example, you may want to wait until after you've secured your venue and set a date. This way, you can provide your wedding party with concrete details about the location and timing of the wedding. It also helps to have a clear vision of your wedding theme or style before asking, as this can influence their attire and role in the wedding.

Don't Leave It Too Late: On the other hand, don't leave it until the last minute to ask. Your best man and groomsmen will likely play essential roles in your wedding, and they need time to prepare. They may want to be involved in pre-wedding events, help with planning, or simply ensure they look their best for the big day. Asking them too late may cause unnecessary stress and could potentially lead to scheduling conflicts.

Be Mindful of Their Commitments: Keep in mind that your friends may have other commitments, such as work, family obligations, or other weddings they are attending. By giving them a reasonable amount of notice, you increase the chances that they will be available and able to participate fully in your wedding celebrations.

In conclusion, finding the right timing to ask your best man and groomsmen is crucial. Give them enough notice, but not too much, and try to align your request with key milestones in your wedding planning. Remember, they are an important part of your special day, and you want to give them the opportunity to be fully engaged and excited about the event.

Activities: Planning your proposal around a shared activity can make it more special and memorable

Planning your best man and groomsmen proposal around a shared activity is a great way to make it more special and memorable. Here are some activity ideas to consider:

Golfing

If you and your best man-to-be have been golfing buddies for years, why not ask them while enjoying a round of golf? You could even give them a box of personalised golf balls to mark the occasion.

Watching the Game

If you and your future groomsman are sports fans, invite them over to watch the game and pop the question during halftime. You could also give them a gift that ties into their favourite sport, like a baseball-themed deck of cards.

Hiking

Take your groomsman-to-be on a hike and ask them to be part of your special day while enjoying the great outdoors. You could even make it a group activity and invite all your groomsmen for a fun-filled day.

Coffee or Lunch

Meet up with your groomsman-to-be for a coffee, lunch, or a drink, and ask them to join your wedding party. This is a great opportunity to have a heartfelt conversation and share why their presence on your big day matters to you.

Concert or Comedy Show

If you and your groomsman share a love for music or comedy, take them to see your favourite band or comedian. This shared experience will create a memorable backdrop for your proposal.

Shared Hobby

Think about the hobbies and activities you enjoy doing together. It could be anything from painting to fishing. Plan your proposal around this shared hobby to make it more meaningful. For example, if you both love fishing, you could give them a personalised fishing lure as a token of your friendship and proposal.

Remember, when planning your proposal, it's essential to choose an activity that reflects your relationship and shared interests. This will make the moment more special and memorable for both of you.

Frequently asked questions