Choosing Groomsmen: A Guide To Picking Your Wedding Entourage

Choosing your best man and groomsmen is an important part of wedding planning. While it can be a tricky decision, there are a few things to consider that might make the process easier. Firstly, it's important to remember that there is no rule that says you have to have a certain number of groomsmen or even a best man at all. If you have a brother, a male cousin, or a close male friend, they are often a natural choice for best man. If not, you could consider asking a female friend or family member to be your best man. When it comes to choosing your groomsmen, it's a good idea to think about who has been there for you through thick and thin and who will be happy to support you throughout the wedding planning process. You might also want to consider including family members such as brothers, cousins, or even your partner's siblings if you are close to them. If you have multiple brothers, you could include them all or make an agreement on which brother will be part of your wedding. It's also worth thinking about the number of groomsmen you will have – this might depend on the size of your wedding and how many bridesmaids your partner has. Remember, it's your wedding, so don't feel pressured to follow traditions if they don't feel right for you.

Choose someone who's been there for you

When it comes to choosing your best man, it's important to select someone who has been there for you through thick and thin. Here are some reasons why choosing someone who has been a steadfast supporter is crucial:

Reliability and Trust

Reliability is key when choosing your best man. Opt for someone who has been a constant presence in your life and who you can count on to be by your side through life's ups and downs. This person should know you inside out and be able to provide support and guidance whenever needed. They should also have your best interests at heart and be willing to put their own preferences aside to plan a celebration that aligns with your tastes and preferences.

Strong Communication Skills

Effective communication is essential for a best man. Choose someone who can communicate well with you, the groomsmen, and other members of the wedding party. They should be able to rally the group together, address any concerns, and ensure everyone is on the same page. Additionally, strong communication skills will be crucial when it comes to delivering the best man's speech, a task that often requires a delicate balance between humour and sincerity.

Leadership and Organisation

The best man often acts as the de facto leader of the groomsmen, so it's important to choose someone with strong leadership qualities. They should be able to take charge, delegate tasks, and ensure that everyone is on track with their responsibilities. Organisation is key, as they will be handling various time-sensitive tasks, from planning the bachelor party to ensuring the groomsmen have ordered their attire.

Understanding and Empathy

Choose a best man who understands you and your relationship with your future spouse. This person should be able to speak genuinely about your relationship during the best man's speech, adding a personal and heartfelt touch to the celebration. They should also be able to offer emotional support and be a good listener if you need to share any worries or concerns leading up to the wedding.

Proactivity and Problem-Solving

Look for someone with a positive, can-do attitude and strong problem-solving skills. A good best man will be proactive in addressing any issues that may arise, ensuring that your wedding day runs as smoothly as possible. They should be able to handle any last-minute hiccups calmly and efficiently, allowing you to fully enjoy your special day without worrying about the logistics.

Remember, while family members are often considered for the role of best man, it's important to choose someone based on their ability to fulfil the role's responsibilities and provide the support you need. Whether it's your brother, cousin, or longtime friend, select someone who embodies the qualities you value most and who will stand by your side on one of the most important days of your life.

Pick a close family member

Picking a close family member as your best man is a great option for many grooms. The role of the best man is often filled by the groom's brother, and if you have more than one brother, you can even have two best men! This can be a good way to avoid hurt feelings and divide up the various duties of the best man.

A close family member is likely to know you well, have a good relationship with your fiancé, and be able to plan a bachelor party that suits your tastes. They will also be aware of any family traditions that are important to uphold on the day.

If you don't have any brothers, you could consider another close family member, such as a father, uncle, or cousin. You could even ask your bride's father to be your best man, or choose together with your bride-to-be. This can be a great way to honour a family member or close mentor and will likely be a very special moment for them too.

Remember, the best man should be someone you trust, who knows you well, and who can handle the organisational aspects of the role. They will be responsible for guiding the groomsmen, so it's important to pick someone who can communicate effectively and delegate tasks.

Select a friend from each life stage

When choosing your groomsmen, it's a good idea to select a friend from each life stage. This is a great way to represent all facets of your journey so far and bring people together. Here are some tips to help you choose your groomsmen, including a friend from each life stage:

Childhood Friend

A friend from your childhood is likely to have known you the longest and has been through different life stages with you. They have seen you grow and change over the years and have a unique perspective on your life. They may also know your family well and have a good relationship with them. Consider choosing a childhood friend as one of your groomsmen to honour their long-standing friendship and the role they have played in your life.

Teenage Years Friend

Friends from your teenage years have likely been through some of the most formative years of your life with you. They may have been by your side during your first adventures in independence, such as learning to drive, first jobs, and navigating the challenges of adolescence. They will have shared experiences and memories that are unique to that time in your life. Choose someone from this life stage to represent the fun, carefree days of your youth and to honour the bond you formed during those pivotal years.

College/University Friend

Friends made during your college or university years often become like family. You may have lived together, studied together, and supported each other through the challenges of higher education. They know the hard work and dedication it took for you to get where you are today. Choose a friend from this life stage to represent the growth and learning that came with this stage of your life and to celebrate the bond formed during those intense and transformative years.

Adult Life Friend

Friends from your adult life know you as the person you are today. They have seen you navigate the challenges and responsibilities of adulthood and may have been a source of support during difficult times. They may also be friends with your partner and know the dynamic of your relationship well. Choose someone from this life stage to represent who you are in the present and to honour the unique perspective they bring to your friendship.

When selecting groomsmen, it's important to choose people who have supported you through different life stages and will continue to be a part of your life in the future. It's also a good idea to consider their relationships with each other and how they will fit together as a group. Remember, there is no set number of groomsmen you need to have, so choose only those who are truly meaningful to you.

Opt for a small group

Opting for a small group of groomsmen can be a great way to go, especially if you're having a small or intimate wedding. While there's no one-size-fits-all answer to how many groomsmen to choose, here are some reasons why a small group could be the way to go:

Budget-Friendly

Having a smaller group of groomsmen can be more budget-friendly. Each groomsman will likely need to purchase or rent attire, and there may be other expenses like travel or accommodations. By keeping the group small, you can reduce these costs.

Less Coordination

A smaller group means less coordination and communication for the groom. With a larger group, there are more people to keep track of, more chances for miscommunication, and more reminders needed. A small group simplifies the process and makes it easier to stay organized.

More Intimate

A small group of groomsmen allows for a more intimate and close-knit dynamic. Each groomsman can play a significant role and have a deeper connection with the groom. This can create a more supportive and meaningful experience for everyone involved.

Venue Considerations

The size of your wedding venue may also influence your decision. If you're having a small wedding in a tight space, a large group of groomsmen might feel cramped and uncomfortable. Opting for a small group can help ensure everyone has enough room to breathe and move around.

Less Pressure

Choosing a small group of groomsmen can take some of the pressure off. It can be a challenging task to select groomsmen, especially if you have a large social circle. By opting for a small group, you can focus on your closest friends or family members without feeling the need to include everyone.

Ultimately, the decision on how many groomsmen to choose is a personal one. A small group can offer benefits such as cost savings, easier coordination, and a more intimate dynamic. However, the most important factor is to choose individuals who are meaningful to you and who will bring value and joy to your special day.

Ask them in person

Asking your best man and groomsmen in person is a great way to make the moment more special and memorable. Here are some tips and ideas to help you pop the question:

Best Man

The "will you be my best man?" conversation can be nerve-racking, but it's a meaningful way to honour your relationship and mark the moment. Traditionally, it's best to ask in person. Here are some ways to make the ask more special:

• Lead the conversation towards your relationship and how you've found the right person. Then, transition into expressing how much you appreciate your friend and that you would be honoured to have them by your side.
• Make it a special moment by taking your friend out for a drink or dinner. You can also invite them over for a hangout session and pop the question.
• If you share a hobby or interest, incorporate it into your proposal. For example, if you both enjoy cycling, plan a "bromantic" pre-wedding bike trip and ask during the trip.
• Give them a small gift or token, such as a bottle of their favourite drink, a book, or a personalised item, along with a note asking them to be your best man.
• If you want to keep it simple, a straightforward "will you be my best man?" will often do the trick.

Groomsmen

Asking your groomsmen in person is also a great way to make them feel valued and appreciated. Here are some ideas:

• Invite your groomsmen-to-be to a get-together, such as a backyard BBQ, a hiking trip, or even your engagement party. During the event, give a short speech about why they are important to you and why you want them to stand by your side on your wedding day.
• Ask each groomsman individually. Take them out for a meal or hang out with them one-on-one, and then pop the question.
• Send them a formal invitation to be your groomsman. This can be a thoughtful way to express your feelings and ensure you don't leave anything unsaid.
• Give them a gift, such as a drink glass, beer mug, or a gift box with items related to your wedding or your shared interests.
• If you prefer a more light-hearted approach, use humour or a good-natured joke. Send them a card with a funny one-liner, such as "You'd probably scrub up well" or "You're being promoted from wingman to groomsman."

Frequently asked questions