12 Creative Ways To "Propose" To Your Groomsmen

Mar 01, 2019

12 Creative Ways To "Propose" To Your Groomsmen

You've finally boiled down your list to a select privileged few that will be asked to partake in your wedding ceremony as a groomsman. Now that you are ready to propose to your groomsmen, here are a few creative ideas as to how you can do so.

1. Have An Invitation Engraved On Their Favorite Bottle.

You are familiar with your prospective groomsmen's favorite spirits. A way that you can creatively ask them to be your groomsman is by displaying an invitation right on their favorite alcoholic drink. There are many services that will engrave a bottle for you with a message.

Shop Groomsmen Barware

2. Use A Mail Subscription Service.

In the past couple of years, subscription "boxes" have become very popular. For a monthly fee, you subscribe to a service where a company will compile and mail your favorite things - whatever they may be, there's a subscription box for everyone. Select a subscription box that represents your groomsman or the relationship that you share with them. Many of these subscription boxes have free or inexpensive introductory offers. If you are not genuinely interested in keeping a subscription but want to invest in a box for the sake of your friend, then you can use the trial period just to secure a box for them. In the box, send a note thanking them for the experiences shared with you, with a formal invitation as a groomsman.

3. The Standard Cigar.

The cigar represents the unique sense of brotherhood between good friends - and it's the perfect prop to use to propose to your groomsmen. Step up your creativity by securing the cigar to a piece of quality stationery, or on an envelope with a letter inside of it, asking them to be your groomsmen. It's a simple way to ask the question, but one that is noted by nonchalant emotion.

Shop Groomsmen Cigar Gifts

4. Custom Cufflinks

Groomsmen Cufflinks

During the ceremony, there are going to be many tears, many faces, and many cufflinks. Wedding attire for men can be a bit monotonous - add some flare by giving your prospective groomsmen some custom cufflinks. Inside these cufflinks, there can be a short message or phrase unique to each participant. They may ask what they are for. Tell them that you expect them to be your groomsman. Etsy is a market place for professional creatives, making it the place to visit if you want custom items.

5. Hilarious Cards.


If you know your friends can appreciate a good joke, then consider giving them a pack of compiled funny jokes. If you want to add a personal touch, you can create your own cards full of inside jokes that you know will have your friends roaring with laughter. At the end of the cards, you can write a humorous letter noting how they will have an important assignment, with pictures of fingerprints at the bottom, and space for them to sign. The letter should have enough nuance to give them the impression that they are being informally asked to be a groomsman.

6. Plan An Event.


You can kill two birds with one stone by inviting all your prospective groomsmen to an event, like lunch, a favorite pub, or a weekend hangout that requires traveling. You can make the situation as informal or formal as you see fit. Make sure to book an event or space that commemorates your friendship, or represents a certain milestone in your groomsmen's lives. They will cherish the fact that you've remembered an important aspect of their life.

7. Get A Starter Kit.

Hint at the invitation, by giving your prospective groomsmen a "starter" pack. This starter pack can include the essentials - cufflinks, a bowtie or a printed tie, and a small bottle of their favorite drink. The moment that you give the gift to them will be a random moment, but after opening the contents of the starter pack, they should know what you are hinting at. You can then solidify the moment by asking them if they would be able to be part of your groomsmen pack.

You will also help alleviate some of the costs of being a groomsmen.

Shop Groomsmen Gift Sets

8. Educational Booklet on Ties And Different Knots.

Creating the perfect knot on a tie can be a bit frustrating for many, especially if ties aren't a normal part of their everyday routine. An educational booklet on ties will be helpful, giving them time to practice. Give them the card and tell them that you are excited to see how good - or bad - their tie knots are going to be at your wedding. They'll catch on.

9. Give Them Directions To A Nearest Tailor Or Tuxedo Service.

Print out a screen shot of tailor or tuxedo rental services in your prospective groom's area. On the back, write a personal story, noting how excited you will be if they accept your invitation to become a groomsman. This is an informal, yet funny way to invite your groomsmen.

10. Or You Can Go Over The Top.

There's always the option of being so obvious, and so over the top, that it spills into a humorous moment. Embarrass your boys at work by sending them flowers, with official invites. Or you can ask them in private while still passing around roses. The idea is to embarrass them, and having an awkward, yet joyous moment.

11. A Bouquet of Liquor.

Instead of flowers, consider getting them a bouquet of liquor. Miniature bottles suspended on sticks inside of a vase or pot looks just like flowers - except they are a lot more fun and useful. Gather your groomsman's favorite liquor and spirits and place them in a pot like a bouquet. Make sure that you leave a note, asking them to be your groomsmen.

12. A Simple Invitation

If you are a man of few words or have a prospective groomsman that lives far, consider sending them an invitation card. You can write in the card, making it as personal as you want - or you can simply send the card their way, with your name on it. An invitation card makes a statement while still keeping it casual.

 Read our new 21 Best Groomsmen Gifts of 2019

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