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3 Creative Ways To Ask A Guy To Be Your Groomsmen

You’ve popped the question, she said yes, and now you’re about to ask yet again another question. This time around, though, you’ll be asking your best buddies to stand with you on the big day as your groomsmen. 

Wedding boutonniere on a wooden table

Although you might’ve mentioned the matter a few times before over drinks, meals, or get-togethers, it’s still essential that you take the time and make it formal. Asking a guy to be your groomsmen is among the many tasks you need to take care of as the groom-to-be. 

Groomsmen proposal 101

Your friends may already be expecting it somehow, but it doesn’t mean you won’t have to go out of your way just to ask the big question. Saying ‘will you be my groomsman?’ may sound like a simple question, but as you try to find ways to say it, you’ll realize it’s not as easy as it seems. 

If you’re having a hard time figuring out what to do, take a look at these creative ways on how you can ask a guy to be your groomsmen: 

1. Send them a unique gift 

Even when you know they’d say yes, you can’t help but feel a bit anxious as you wait for their response. If you want to skip the worrying part, you can come up with unique groomsmen gift ideas that you know your crew won’t be able to resist. By unique, it has to be something they probably haven’t seen from previous weddings they’ve been to. 

For instance, you can include a note with the gift asking them to be your groomsmen. You can choose to handwrite the messages or have them calligraphed for a more formal and elegant appeal. Use a special box or container for your gift to make a good impression. Your groomsmen will surely be delighted to find that your gift is a complete package––from packaging to the actual product itself. (1)

From personalized Bluetooth speakers to whiskey decanters, gunmetal beer mugs, cigar holders, pocket watches, and pocket knives, don’t hesitate to go all out if you have the budget and the knack for it. After all, it’s not every day that you get married, and you surely want to share such a blissful experience with your best buddies. (2)

2. Curate a groomsman starter pack 

If you feel like splurging and you think your crew deserves more than just a single gift, there’s one idea that’ll stand out from the rest—a starter pack for your groomsmen. A starter pack means curating a collection of stuff that you think will be helpful for the boys in fulfilling their duties as part of your entourage. Of course, there’s also the factor of giving them things that you know they’ll appreciate. 

Curating a starter kit for your best guys is like giving them a glimpse of what’s about to happen as the big day approaches. For example, a preparation kit containing matching socks, cuff links, leather belts, suspenders, and bow ties is a good start. Your gang can already sense that it’s going to be a day of matching looks and dapperness, which can be pretty exciting knowing that they’ll be doing it with you. 

If you want a more curated box, you can also include a shaving kit and other hygiene paraphernalia to complete the personalization you want to achieve. 

3. Invite them out for a round of drinks 

Boys will be boys, as they say, and what better way to lure them in than offering free drinks for the night? It may not be that creative at first glance, but you can always add a little twist here and there, so they won’t easily anticipate that you’re about to pop the question. One idea is to conspire with the bartender or the club owner, and ask if they could serve the beer or drinks in customized glasses or mugs. Your potential groomsmen will definitely be in awe upon seeing the glasses with their name or initials on them. (2)

Moreover, if you want a more dramatic proposal, you can just grab the mic in the middle of the night and call the attention of your best buds as they toast the night away. Ask them outright if they’re willing to be your groomsmen, and most likely, they’ll say yes. For sure, you’ll end the night cheering on and drinking your hearts out. Next thing you know, the boys are so elated they’re already planning for an epic bachelor’s party for you. (3)

Group of friends drinking


Exciting times are surely ahead the moment you get engaged. Moving forward, there’ll be plenty of planning, decision-making, and preparations involved to turn your dream wedding into a reality. One of the things you need to do is ask your wolf pack if they’ll be willing to step in as your groomsmen. (4)

Take the opportunity to ask them in various non-conventional ways they might haven’t experienced before. You can send them a unique gift, curate a groomsmen starter pack, or ask them out for a round of drinks.


  1. “10 Groomsmen Proposal Ideas They’ll Love”, Source: https://www.brides.com/groomsmen-proposal-ideas-5101234
  2. “The Best Gifts for Groomsmen, According to Experts”, Source: https://nymag.com/strategist/article/best-gifts-for-groomsmen.html
  3. “What’s a best man to do?”, Source: https://edition.cnn.com/2013/12/20/living/matrimony-wedding-party/index.html
  4. “Wedding Party Roles and Responsibilities”, Source: https://www.thespruce.com/whos-who-in-the-wedding-party-3489947

What do you think?

Written by Mark Greene

Mark Greene is writer and life coach dedicated to helping men to perform at peak level. He shares dating advice, style tips and strategies for building wealth and success.