How to Ask "Will You Be My Groomsman?"

There are some simple yet creative ways to ask your best friends to be in your wedding. Here are some basic groomsmen proposal ideas:

  • Engraved invitation
  • Send them a box of stuff
  • Give them some smokes
  • Improve their style with a classy gift
  • Use those comedy chops
  • Bring them all together and ask at the same time
  • Buy their tuxes (and make them wear them to your wedding)

The Big Ask

Figuring out how to ask a groomsman to be in your wedding is a tough task. You can't just drop a text in a group chat saying "congrats on making the cut." You're better than that, so we're here it get the groomsmen invitation ideas flowing.

When thinking about how to ask guys to be groomsmen, frame the question as if someone were proposing to you. What groomsmen invitation idea would blow you away? Now that you are ready to propose to your groomsmen, here are a few creative ideas to get you started.

1. Engrave Their Groomsmen Invitation On Their Favorite Bottle

Groomsmen proposal gifts

You are familiar with your prospective groomsmen's favorite spirits. A way that you can creatively ask them to be your groomsmen is by displaying an invitation right on their favorite alcoholic drink in a custom bottle. There are many services that will engrave a bottle for you with a message. You can also buy them personalized mugs or glasses to pour their liquor into so it fits nicely at their bar at home.

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 it may be, there is 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, making it the perfect groomsmen invitation idea. 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 with sentimental value.

Sending a cigar case or personalized humidor is another way unique way to ask your friend to stand beside you on your wedding day.

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, so add some flair by giving your prospective groomsmen some custom cufflinks.

Inside these cufflinks, there can be a short message, phrase or initials unique to each participant. They may ask what they are for. Tell them this is how to ask guys to be groomsmen. We have an excellent collection of cufflinks made in different shapes and materials so your groomsmen are dressed to the nines on your big day.

5. Hilarious Cards.

Groomsmen proposal cards

If you know your friends can appreciate a good joke, then consider giving them a pack of compiled funny one-liners. If you want to add a personal touch, you can create your own proposal 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 a travel bag. 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 bow tie or a printed tie, and a small bottle of their favorite drink. Select a unique gift box for each of your Groomsmen to match their personality and interests. Or  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.

The best way to bring a pack of groomsmen together is by getting matching gifts. And this groomsmen invitation idea is easier on your wallet because it's always cheaper to buy in sets rather than individually.

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 should catch on to the groomsmen invitation idea quickly.

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

Print out a screenshot of a tailor or tuxedo rental service in your prospective groomsmen'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 ask your groomsmen.

10. Or You Can Go Over The Top.

There is always the option of being so obvious and so over the top with your groomsmen invitation idea that it creates a humorous, unforgettable 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 while creating 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. The Simplest "Will You Be My Groomsman" Gift

Groomsmen cards

If you are a man of few words or have a prospective groomsman that lives far away, 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.

Will You Be My Groomsmen?

There are endless ideas for how to ask a groomsman to be in your wedding, but hopefully this provides a good base for your brainstorming session. And if these ideas sound too expensive and you'd like to keep each invitation or groomsmen gift under $25, we have a vast collection of gift ideas your groomsmen will love.

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