Choosing your best man doesn’t sound like a particularly difficult task. Here’s the way every unmarried guy thinks it goes down:
You pick your brother–unless you two can’t stand each other, or he’s in prison. If not your brother, your best friend. Simple. What does he have to do anyway? Just get you drunk the night before the wedding and put the rings on his keychain so he doesn’t forget to bring them to the ceremony.
Well, as we’ve written elsewhere, there’s a lot more to being the best man. Once you take all those things into consideration, you may find it harder to choose your best man that you anticipated.
Know what you’re asking of your best man before you start narrowing down your candidate list.
1. Pick Someone Who’s Capable
A best man should be useful to the groom, helping him with preparations that he either doesn’t want to deal with, or can’t.
As the head groomsman, the best man should make sure all the other groomsmen have their shit together: their tuxes fitting right, their roles in the ceremony clear, their understanding of wedding decorum firmly established.
As wedding wingman, the best man can help the bride and groom with some pre-wedding preparations: organizing a list of toasts for both the rehearsal dinner and the wedding reception, arranging the “getaway” car to transport them to the honeymoon suite, and making sure the groom brings the wedding license.
Find a best man who’s well organized and task oriented. Go with your best friend who works as an accountant instead of your other best friend, who’s only organizational skills are lining up drinks for his buddies at happy hour.
2. Pick someone sociable
On the other hand, you don’t want an office manager or a hall monitor. A lot of the best man’s job does require an agile touch with in-laws, guests, vendors, and other event professionals. You want someone who is at ease with other people, who likes to schmooze and be social. You want someone who is confident enough that their glad handing will seem unforced and natural.
3. Pick someone discreet
One of the few duties that everyone expects every best man to complete is the Best Man Toast. This is an area where the groom will not have direct influence (unless you vet the speech beforehand, which is, frankly, a little weird).
You can, however, eliminate someone from the running if you are worried they’ll say something tasteless or embarrassing. If you’re pretty sure their speech will be a dumpster fire, then pick someone else to do the job.
4. Ask him in person
When you’re ready to make your offer, make it in person. It’s not only more special for them, but you’ll get to see the reaction on their face. If you see a look of dread and panic, start back peddling; surprise and pleasure, and you’re good to go.
Try not to make your offer in front of other friends, in case they were thinking they might be the one chosen. Instead, visit with them separately and ask them to be one of your groomsmen, or give them another role in your wedding: an usher, say, or an official bachelor party beer chugger.