It’s Time To Step Up Your Groomsmen Proposal Game

by | Gifts and Favors, Groom, Tips and Tricks


Mr Houndstooth

It's Time To Step Up Your Groomsmen Proposal Game

Image by gmphotographics via Claudia & Ben’s Classic Canberra Wedding

So you’ve done the hard yards and managed to whittle down your selection of groomsmen to just a handful of your nearest and dearest.

bCongratulations, that was the hard part.

Now comes the fun part: how should you ask them?

It can be tempting to just blurt out the news over a few pots at the pub, or shoot off a quick text (please, no emojis).

But come on, the groomsmen play a key role in one of the biggest days of your life, why not put in a little bit of extra effort to make it memorable?

With the right amount of thought, you and your best mates will be talking about what is commonly known as ‘the groomsmen proposal’ for years to come.

Here’s a few ideas to get you started:

The Hip Flask

Photo: My Personal Memories

Image by My Personal Memories

Choosing a groomsmen-related hip flask works on so many levels, the first being that there is no confusion over what you are asking. It’s pretty clear that this is a groomsmen request from the outset.

The next would be that you can use the gift on the day of the actual wedding.

Tip: Go the extra mile and fill each flask with your fave whisky. It’s a nice touch your groomsmen will be sure to appreciate (in moderation, of course).

Personalised Stubbies

Image by Brewtopia

Image by Brewtopia

While probably not as classy as the hip flask, the personalised stubby or slab is sure to leave an imprint on your groomsmen.

Melbourne-based company Brewtopia offers a range of “personalised beverage products”.

“We have a range of label design templates that can be personalised.” Brewtopia General Manager Jessica Simes says.

“Or they can download the “Upload Your Own” template and create the artwork from scratch to match wedding invites for example.

“The creative options are endless using this option and people tend to have fun with it.

They offer a Lager and Pale Ale which they say is brewed by one of the country’s “top craft brewers”, and there’s cider on the menu too.

The Wolfpack Card

Wolfpack card. Photo Crimson and Clover Gift

Image by Crimson and Clover Studio 

Will you join my wolfpack? Cute, right?

While these handmade cards aren’t specifically groomsmen or wedding related, rest assured, the message will be delivered. If not, you can add the actual message inside!

Created by New York outfit Crimson and Clover Studio, the design has immediate impact once it comes out of the envelope.

As creator Rachel says:

“One day when I was watching Oprah learning how to be my best self, it dawned on me – why don’t I make some funny greeting cards and see if anyone likes them?”

Well, we do, Rachel. We do.

Cigar Box

Cigar box. Photo: Cherished Heritage

Image by Cherished Heritage

If your groomsmen enjoy a cigar then this may be the perfect way to ask that question.

The Groomsman Cigar Gift Box, created by US company Cherished Heritage, features a black cardstock tuxedo on the front and opens up to reveal the message inside.

You can even choose what you want the message to be inside, including our personal fave:

  • Time to suit up!

As well as:

  • I can’t say “I DO” without you!
  • Your services are requested!

Note: You have to provide your own cigar and there’s even an option for a ‘candy cigar’ in case you are gifting to someone who doesn’t smoke.


Personally, I probably let the ball drop on this when it came to my own wedding. In lieu of any grand gestures, I blurted out who I wanted to be in my bridal party over a casual dinner.

There was something about the announcement which caught me a bit by surprise.

I almost didn’t recognise that it was such a big deal.

But in hindsight, putting together something a bit special which featured one or all of the above would have been a fun and memorable way of having that conversation.

And having a prop would have eased the awkwardness that can often come attached to honest, emotional conversation.

My pick? I can’t get past those flasks. Suave and practical.

Ms Chinoiserie Says: The Wolfpack card gets my vote; such a fun and light-hearted way to keep those “big deal’ butterflies under control!

About Mr Houndstooth: I am a happily married man. I enjoy a fine whisky, a new suit and swashbuckling around town with my beautiful bride. Looking back on my wedding day always makes me smile, even though it began to rain just as I said ‘I do’.



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