How to Ask Your Best Man and Groomsmen to Stand by You on Your Big Day - Swagger & Swoon

How to Ask Your Best Man and Groomsmen to Stand by You on Your Big Day

Asking your closest friends to be a part of your wedding is a significant and memorable moment. Your best men, ushers and groomsmen will be by your side throughout your journey to the big day, 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? We’re here to help with some top tips for making this process special, and we've also included some great proposal gift ideas to make the moment even more unforgettable.

1. How Many Groomsmen Should You Ask?

First off, the number of groomsmen you ask depends on a few factors. There’s no hard rule about the number of groomsmen—it all depends on the size of your wedding and your personal relationships. Some couples like to balance the number of groomsmen with the number of bridesmaids to create symmetry in photos and during the ceremony.

Generally, small weddings might have 2-3 groomsmen or a single groomsman and a best man, while larger weddings might include 5-7 or more. The important thing is to choose the people who mean the most to you, whether that’s your brother, best friends from childhood, college mates, or close colleagues.

2. Creative Ways to Ask Your Groomsmen

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. Here are a few ways to ask them:

Handwritten Notes: A heartfelt, personal letter is a timeless way to ask. Reflect on your friendship and share why having them as part of your day matters.
Surprise Dinner or Drinks: Gather your groomsmen for a dinner or drinks, then pop the question to the whole group. It’s a great way to celebrate the moment together.
Sports or Game Day: If your group is into sports, consider asking them during a game, perhaps by wearing personalized shirts or caps that say “Groomsman” or “Best Man.”
Proposal Gift: This is becoming a popular choice, either to hand out or send to your groomsmen if they live far away, it's a lovely way to add a little surprise to the moment. A fun gift, that's going to be useful for the big day is even better! Looking for some inspiration? Have a look at our range of proposal gifts>

3. Should You Give Gifts?

While it's not required, it’s a nice gesture to give your groomsmen a gift as a token of appreciation for being part of your special day. A gift serves as a meaningful keepsake of your wedding, and it’s also a way to thank them for their time and effort.

Proposal gift boxes are a popular way to pop the question. They often include personalized or themed items that are not only thoughtful but practical for your wedding day and beyond.

4. Best Proposal Gift Boxes

Here are some thoughtful and stylish proposal gift box ideas to help you ask your groomsmen to stand by your side on the big day:

Cufflinks: A classic and timeless gift, cufflinks are a perfect addition to any wedding outfit. They’ll not only look great on the big day but also serve as a memorable keepsake for future formal occasions.

Socks Box: Personalized or fun patterned socks are a playful way to add some personality to your groomsmen’s attire. Whether it’s a pair that matches your wedding colors or socks featuring something unique to each friend, this is a practical and quirky addition to any proposal box.

Tie Sets Box: A tie set is a great gift to ensure that your groomsmen coordinate perfectly on the day. Include a matching tie, pocket square, and even a lapel pin, all in the color or pattern that fits your wedding theme. This gift is both useful and stylish, ensuring they’re ready to suit up for your big moment.

Personalised Proposal Boxes from Swagger & Swoon: If you want to make things extra special, Swagger & Swoon offers bespoke, personalized proposal boxes tailored to your groomsmen. You can fill these boxes with items like ties, socks, cufflinks, or even engraved flasks. With customization options, each groomsman can receive a gift that feels personal and unique, making the moment even more meaningful.


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Whether you decide to keep it simple or go all out with a personalized proposal box, remember that 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.

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