Best Man Duties: How To Ask And What To Expect

Asking someone to be your best man is a nerve-racking task. You want to impress your pal and mark the moment. While some people just ask their friends, others go for a more elaborate proposal. If you're looking for creative ways to pop the question, here are some ideas to get you started.

Gifts to accompany the proposal

When it comes to popping the question to your best mate, you can go as simple or as extravagant as you like. Here are some gift ideas to accompany your proposal:

A gift is a great way to make your proposal feel official and show your friend how much their support means to you. Here are some ideas for gifts to accompany your proposal:

• Custom golf ballsand a round of golf: Get a set of personalised golf balls for each person and invite them out for a round of golf. This is a fun way to get their attention and they will be reminded of you and your wedding every time they tee off.
• Stylish proposal boxes: These boxes can include goodies like personalised flasks, sunglasses, and socks with labels asking "Will you be my groomsman?".
• Monogrammed handkerchiefs: Gift your groomsmen a linen handkerchief embroidered with their initials. This is a stylish and practical gift that they can use to wipe away their tears during your emotional wedding ceremony.
• Cocktail proposal boxes: Alcohol is a classic choice for a wedding gift. Pair a bottle of bourbon with a gift box so your groomsmen can craft their own cocktails at home.
• Sleek cigar cases: For a gift that is inspired by the past, get your groomsmen engraved cigar cases and cutters. Gentlemen have been gathering to smoke cigars and enjoy each other's company for decades.
• Custom dress socks: Ensure your groomsmen don't get cold feet with these funky socks that come with a personalised label asking, "Will you stand with me as my groomsman?".
• Pop culture tie bars: If your groomsmen are fans of Star Wars, get them a tie bar designed to look like the hyperdrive outer space scenes from the movie, which even glows in the dark.
• Trendy travel tumblers: A Stanley cup is a winning gift idea for your best man or groomsmen. Choose from a range of colours, sizes, and customisation options to fit their personalities and tastes.
• Wooden valet trays: Made from solid acacia wood, this elegant valet tray will give your groomsmen a special spot to keep their accessories safe. Have each one engraved with their monogram for a personal touch.
• Custom guitar picks: If you and your crew were in a band in high school, get your guys wooden guitar picks customised with their names and wedding party roles. You can also choose engraved boxes for a polished presentation.
• Engraved wooden watches: Your groomsmen can wear these personalised timepieces for your wedding and beyond. Each one is crafted from sandalwood and engraved with their wedding title, monogram, and the date of your special day.
• Custom tape measure: Taking a unique approach can pay off. A tape measure might be an unusual pick, but it can be engraved with a sweet message like, "A man is measured by the quality of his friends."
• Personalised beer labels: Get creative with your proposal by using custom beer labels that say "Chug means yes" or "Groomsmen chug means yes".
• Customised hip flasks: A quintessential groomsman gift, a bespoke hip flask will deliver a little pre-best man speech Dutch courage.
• Personalised pocket watch: An art-deco style engraved silver pocket watch is a snappy addition to any suit and will encourage your best man to be on time on your wedding day.
• A tie: If you've decided on your wedding suit styling, kit out your best man early by giving him a tie when you pop the question.
• Monogrammed cufflinks: Sleek and understated monogrammed cufflinks will go with every suit and shirt combo and become a go-to for decades to come. He’ll think of you every time he gets dressed up.
• Bespoke wedding socks: Select a sock style, shade, and gift package and send this to your best man alongside a handwritten note.
• A book: If you're planning a cycling-themed stag do or want to plan a trip away with your best man, get them a book with all the best bike rides in the world.
• Personalised print: Make your best man the star of the show by giving him a movie-style art print with your proposal.

In-person vs by mail

When it comes to asking your best friend to be your best man, you can either do it in person or by mail. There are pros and cons to both methods, and ultimately, it depends on your preferences and your relationship with your friend. Here is a detailed look at the two options:

In-Person

Asking your friend to be your best man in person can make the moment more memorable and special. It allows you to see their reaction and celebrate together. Here are some ideas for in-person best man proposals:

• Plan a bro date or a guy's night out and pop the question in a casual setting.
• Invite your friend to an activity you both enjoy, such as golfing, skiing, paintball, or a sporting event, and ask them during the outing.
• Organise a "man meal" and gather all your friends together at a favourite restaurant to ask them at the same time. This creates a festive atmosphere and allows you to celebrate with everyone.
• Ask your friend during a planned trip or vacation, such as a deep-sea fishing trip or a destination wedding.
• If your friend lives nearby, a simple dinner or get-together at your home can be a perfect opportunity to pop the question in a familiar and intimate setting.

By Mail

On the other hand, sending your best man proposal by mail can be a fun and creative way to surprise your friend. It also gives them something tangible to keep as a memento. Here are some ideas for best man proposals by mail:

• Send a personalised card or a funny card with an old photo of you both. This is a simple yet thoughtful way to pop the question.
• Create a custom gift box with items such as a candle, hot sauce, a tie, cufflinks, a pocket square, or a hip flask. You can even include a handwritten note asking them to be your best man.
• Gift them a bottle of their favourite beverage with a custom label that says "Will you be my best man?"
• Send them a book or a guide related to an activity you both enjoy, such as cycling, along with a note asking them to be your best man.
• For long-distance friends, a handwritten note expressing your friendship and asking them to be your best man can be a heartfelt and meaningful gesture.

Whether you choose to do it in person or by mail, the most important thing is to let your friend know how much their friendship means to you and how honoured you would be to have them by your side on your wedding day.

Timing of the proposal

When it comes to the timing of your "best man proposal", there are a few things to consider. Firstly, while there is no specific "right" time, it is generally recommended to ask your groomsmen as early as possible. This gives them plenty of time to plan and helps ensure their availability, especially if your wedding involves travel. Providing your groomsmen with the wedding date, time, and location when you propose is also important, so they can make an informed decision about their participation.

With that in mind, here are some creative and thoughtful ways to propose to your best man, incorporating the timing element:

• Plan a special outing: Treat your best mate to a day out doing a shared favourite activity, such as golfing, skiing, or even just grabbing drinks. This is a great opportunity to pop the question in a memorable setting.
• Host a "man meal": Gather all your groomsmen-to-be together at a favourite restaurant and ask them all at the same time. This creates a fun and festive atmosphere, and you can even raise a glass to celebrate their acceptance.
• Throw a "wedding party" party: Include your partner in the proposal by bringing together the entire bridal party, including groomsmen and bridesmaids, for a celebration. This could be a casual get-together or a more elaborate themed party, such as "Bad Vintage Wedding Attire".
• Send a handwritten note: For long-distance friends or those who live nearby, a handwritten note is a thoughtful and personal way to propose. It can be short and sweet, sharing favourite memories and thanking them for their friendship.
• Propose with a practical gift: Consider proposing with a practical gift that hints at the timing of your wedding. For example, if you're having a winter wedding, propose with a nice beanie or a pair of sunglasses for a summer wedding.
• Give them a save-the-date proposal: Combine your save-the-date card with a creative proposal idea. For instance, you could send a funny card with an old photo of you both or a custom "will you be my best man?" telegram.
• Propose during a shared pastime: If you and your best mate share a hobby or interest, use it to your advantage. For example, if you both love sports, secure tickets to see your favourite team and pop the question during the game.

Groomsmen vs best man

The best man is the groom's right-hand man and typically has more responsibilities than the groomsmen. The best man is usually a close friend or relative who is asked to stand by the groom's side and support and assist him in any way possible before and during the wedding. The best man is also in charge of the groomsmen and leads all communication and activities.

The best man has a lot of responsibilities, including being the groom's confidante, personal valet, and logistics guru. He is often responsible for planning the bachelor party, choosing and coordinating the wedding formalwear, and giving a best man speech during the reception.

On the other hand, the groomsmen are participants who have important jobs but fewer added responsibilities. They may provide support and assistance to the best man, but ultimately the best man is the leader and point person. The best man will typically ensure the groomsmen know where to be and when, sending reminders and coordinating transportation.

While there is usually only one best man, there can be multiple groomsmen. The best man also has a prime spot next to the groom at the altar, while the groomsmen line up next to him. Additionally, the best man is responsible for keeping the wedding rings safe, while the groomsmen usually have no ring-related duties.

When it comes to gifts, it is not necessary to propose to your groomsmen with an elaborate gift, but it is a nice touch and can make your crew feel extra special. A small, thoughtful gift or a gift that suits their interests and personalities is always a good idea.

• Engrave their invitation on their favourite bottle of alcohol
• Use a mail subscription service that represents your groomsman or your relationship
• Give them a standard cigar, or a cigar case or personalised humidor
• Custom cufflinks with a short message, phrase, or initials
• A pack of compiled funny one-liners or proposal cards full of inside jokes
• Invite all your prospective groomsmen to an event, such as lunch or a weekend hangout
• Get them a starter kit with essentials like cufflinks, a bow tie, and a small bottle of their favourite drink
• An educational booklet on ties and different knots
• Give them directions to a nearby tailor or tuxedo service, with a personal note on the back
• Go over the top and be obvious and humorous, such as sending them flowers with official invites
• A bouquet of liquor, with miniature bottles suspended on sticks inside a vase or pot
• A simple invitation card, especially if you are a man of few words or your prospective groomsman lives far away

Creative ways to ask

There are many creative ways to ask your best mate to be your best man. Here are some ideas:

Gifts

• Custom golf balls and a round of golf.
• Stylish proposal boxes with goodies like a personalised flask, sunglasses and socks.
• Monogrammed handkerchiefs.
• Cocktail boxes with a bottle of bourbon and the kit to craft an Old Fashioned.
• Sleek engraved cigar cases and cutters.
• Custom dress socks.
• Pop culture tie bars.
• Trendy travel tumblers.
• Monogrammed wooden valet trays.
• Luxe grooming products.
• A funny best man notebook.
• Monogrammed packing cubes.
• Engraved whiskey glasses.
• Personalised multi-tools.
• Insulated coffee mugs.
• Music-inspired coasters.
• Groomsmen shot glasses.
• A funny personalised mug.
• Lego sets.
• Personalised zippo lighters.
• Best man fishing lures.
• Baseball-themed playing cards.
• Custom guitar picks.
• Engraved wooden watches.
• A novelty tuxedo hoodie.
• College-inspired pouches.
• A best man skateboard.
• Personalised tape measures.
• Cufflinks.
• A pair of socks.
• Practical wardrobe pieces.
• A custom bottle of their favourite beverage.
• A set of video game-themed proposal boxes.
• A pair of sunglasses.
• A leather weekender bag.
• A dopp kit.
• Skincare products.
• A small deskside tray.
• A picture frame.
• A personalised notebook.
• A hip flask.
• Handcrafted cufflinks.
• A personalised beer mug.
• A leather toiletry bag.
• A humorous proposal card.

Activities

• A "man meal" where you gather all the guys together at a favourite restaurant and ask them all at the same time.
• A "wedding party" party where you ask all your attendants at the same time.
• A shared pastime like a day on the slopes, the links, or a paintball or ski trip.
• A night out to see your favourite team, comic or band.
• A barber shop visit.

Frequently asked questions