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How to Propose to Your Bros: A Groomsman Invitation Guide

5 min read

How to Propose to Your Bros: A Groomsman Invitation Guide

If you thought getting her to say yes was all the asking you’d have to do, we’ve got news for you: getting married is really just a series of proposals. Sorry, fellas. It’s true.

First, you start with your girl, and then you move on to another super important ask-- the groomsmen proposal.

Once you’ve figured out who you want to stand next to you on the most important day of your life, you’ll realize there are a million ways to ask your guys to do this.

So, if you’re wondering how to ask someone to be a groomsman, we’ve put together this groomsmen invitation guide.

The Best Man Proposal

Before we get into how to ask your guys to be groomsmen, we’d like to mention the best man proposal. Groomsmen proposals and the best man proposal are not created equal. Since you will task your best man with essential things like coming up with cool bachelor party ideasand planning said party, he deserves a little something extra.

Given the extra responsibility your best man will shoulder, it might be a good idea to have this proposal be a little different, a little more ...extra, than your groomsmen proposal. Take the time to make it a little more elaborate. He’s the most special of your guys, and your best man proposal should reflect that.

“Will You Be My Groomsman?” Ideas

Now that we’ve got the preliminary stuff covered, let’s get right into the best way to ask your bros to be part of your wedding.

Send a Card

If you’re worried about having to put together something elaborate, don’t fear. Groomsmen proposal ideas needn’t be super flashy. Something as simple as mailing a card is a perfect way of extending this honor to your best guy friends, but a word to the wise: don't send just any old card.

By “any old card,” we mean that you shouldn’t go to your local drugstore and buy whatever you find there. You can find lots of groomsmen proposal card options online, all of which you can personalize for that extra little touch. Again, the card doesn’t need to be elaborate. Your groomsmen’s name, some reference to “suiting up,” and the ask is all you need.


Engrave an Invitation on a Hip Flask

In the vast world of groomsmen asking gifts, a hip flask is the perfect way to get the job done. Is there anything better than asking your best friends to be part of your wedding than by giving them a practical alcoholic gift? We think not! 

You may be wondering how your groomsmen will know you’re proposing to them with a hip flask. Easy, you can customize the hip flask with a personalized message asking them to be a groomsman engraved on the back.

Plus, your gang can take their hip flasks with them to the bachelor party. Talk about a win-win!

Get Wedding Day Cufflinks

Nothing says, “will you be my groomsman?” quite like a pair of personalized cufflinks for your best friends to wear on your wedding day. Most of the time, having their initials engraved on the cufflinks costs a nominal fee, and it’s a great way to give everyone an affordable uniform look.

For better or for worse, there are tons of options when it comes to this gift, so make sure when you purchase these, you have a clear idea of what look you’re going for. Also, if you’re planning to get your groomsmen a gift like a watch that they can wear for the wedding, it’s important that it matches or complements the cufflinks.

Pro Tip: A pair of wood cufflinks goes great withwooden watches and will give your wedding attire a touch of modern style.


Plan an Event

Getting all your gang together to extend their groomsmen invitations is a fun way to start the festivities, especially if other “will you be my groomsman” ideas don’t appeal to you. Planning an event serves two purposes: you can organize a fun day with your guys, and you can ask your buddies in person.

The event itself is entirely up to you and your budget. It doesn’t have to be anything fancy because it’s just an excuse for the ask. Some good ideas are wine or beer tasting, golfing, or going to a sporting event. Once you have everyone together, you can ask them all at once.

Get Down on One Knee

Speaking of asking everyone together in person, when it comes to funny groomsmen invitations, getting down on one knee is a hilarious way to invite your gang to stand by your side on your wedding day. If your guys have got a great sense of humor, they’ll think it’s hilarious when you propose to them.

Engrave an Invitation on a Cigar Box

Getting your guys a cigar box is another one of those cool ways to ask groomsmen to be in your wedding. You can engrave your invitation on the top of the box with the date of your wedding or their name and “groomsman?”.

Bonus points if you include some cigars in those boxes!

Wedding Day Survival Kit

We know that it’s not always easy to know how to ask someone to be your best man, but one surefire way to do it is with a wedding day survival kit. That’s right. You can ask your guys to be your groomsmen by putting together a package full of items that might come in handy when the big day arrives.

Some items you might want to include in this survival kit are:

  • Mints
  • A lint roller
  • Ibuprofen
  • A sewing kit
  • Post-its and a pen

Not only is this fun and easy to shop for, but these items might also save the day. Find a simple box to put them in, and voila! Your groomsmen proposal is taken care of. 

Record a Video

Gift ideas for asking your groomsmen don’t always have to be gifts. Take the time to record an exclusive video for each of your groomsmen and try to make each one as personalized as possible.

You can personalize the videos by recording them in a place that has special significance to your friendship, and tell your buddy why you want to include him in this exclusive group on your wedding day. Simple and effective.

Send a Text

Last, but certainly not least, if these groomsmen invitations ideas seem like too much, or if you know your guys won’t be into them, feel free to completely disregard all of them and go the easy route. Yep, you can just send your guys a text. The groomsmen proposal doesn’t have to be overly complicated.


Once You Nail the Groomsmen Proposal

It’s time to start thinking about the next most important thing: what you’re going to get your best friends to thank them for being there for you on your big day. It’s never too early to get a jump on your shopping, so take a look at some of the groomsmen gift ideas, as well as some best man gift ideas to show your boy some love.

And there’s no better place for gifts that’ll show your guys just how much they mean to you than Swanky Badger. Not only do our personalized items make great groomsmen proposal gifts, but they also make the perfect present for the guys that will stand by your side on your big day.


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