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​Popping the Other Question: How to Propose to Your Groomsmen

Posted by Man Crates on


Holy moly, you’re getting married. Lots to plan, lots to think about, lots to prepare for. These memories you are about to create will last a lifetime, so you don’t want to blow it. This includes drafting your groomsmen team. Surely your fantasy baseball picks were important, but this, Sir Groom, is the most important draft of all. These are the men (and, perhaps, women) that will support you through the wedding planning process as well as the big day itself. Not sure about how to ask groomsmen to be in your wedding? We’ve got some suggestions on how to lock in your best mates, family members or favorite stranger* for your wedding dream team.
*Here’s our first tip—don’t ask a stranger. That’s a terrible idea. You’re welcome.

FIELDING YOUR ALL-STAR LINEUP


You know the basics—your wedding party will be made up of your closest friends, favorite (hopefully) family members and maybe your best buddies from childhood or college. (Warning: You may also be obligated to include a bride’s brother or bestie too.) Your team will have your back all weekend long and leading up to the festivities, so you should go big when bestowing this honor upon them. A crude “Yo, you wanna be in my wedding” text with penguin emoji will not suffice. Here’s a list of memorable ways to make your intentions known.

1. GIVE A BOOZE-QUET

Why should the single lady with the best hands have all the fun? Guys can appreciate bouquets too. Especially made of salami. Or perhaps a bouquet of booze? Some small liquor bottles wrapped up and presented with an invitation to be a groomsman is a spirited way to get the wedding party in a partying mood.

2. PUT HIS NAME ON IT

Speaking of booze, if a bouquet isn’t quite up your alley, and if you’d like to make it a little more personal, you can engrave their favorite bottles with an invite to be in the wedding party. Deck their favorite spirit out with your question and then pop that sucker open when they say yes. Everybody wins.

3. RAISE A GLASS AND DROP THE NEWS

Take your prospective groomsmen to your favorite local pub—a spot that is meaningful to your friendship could work, or just a spot you know you’ll have fun—order up a round, and make a toast to your future groomsmen.

4. MAKE A GAME OF IT

Invite the gang over for game night and secretly replace a game card with your own “Will You Be My Groomsman?” card. Then watch the surprise play out. This can also work for poker night.

5. HOOK 'EM UP WITH A KIT

This one can contain booze or not. Up to you. But you should probably include it. Make a groomsmen starter kit for each ask-ee. Include some groomsmen essentials, like a bowtie, cufflinks, socks or some grooming goods. They’ll be dishing out a fair amount of dough if they accept the invite, so this can also be a way to help alleviate the costs of you getting hitched.

6. HIT THE LINKS 

Invite your crew out for a day at the local golf course. In the middle of your round, spring the news on each groomsman by giving him a ball with your invitation written on it with a Sharpie. Then, once you’ve all shot the rounds of your lives, proceed to the 19th Hole to celebrate.

7. POINT TO THE SCOREBOARD

Take a page out of the sports fanatic’s proposal playbook. Invite the guys to a game and grease the palm of the scoreboard operator to flash up your invitation between innings. Just make sure you don’t celebrate so much that you get caught on the Kiss Cam.

8. ACT IT OUT

Can’t ask in person due to geographical challenges? Make a video. You don’t have to be Scorsese or have a blockbuster budget to produce a quality movie that moves your pals. Spend a little time coming up with a concept, like “Lego Bachelor Party,” for example, set the scene, shoot it and send.