A question that comes up more frequently than you’d think is whether it is “okay” to have more than one best man in your wedding. Most guys are too embarrassed to come right out and say they are having trouble picking between their buddies, assuming that having multiple best friends is kind of girly in a “like OMG you’re one of my BFFs” sort of way. So, before you down your which-guy-to-pick stress with the help of a flask, we’ll set the record straight. While it is “traditional” to have one best man, there is no reason why you can’t have multiple best men in this day and age. Heck, some guys even have women as “best men.” Just remember, that if you really do have more than one best man, you’ll need to give them all the duties and honors that go along with it (including presenting nice groomsmen gifts), otherwise, they’re really just still be groomsmen.
There are reasons why you might want to have more than one main wingman buttoning up his best man cufflinks in your wedding. For example, imagine that you became friends with a group of two or three guys at the same time (such as grade school, college or wherever) and each has provided the same level of friendship to you over the years. It would be too awkward to delegate one to become a mere groomsmen; pick them all. Or, imagine that you are super tight with your best friend, but you also have a brother. He could be a pesky little brother or a controlling older brother. While you may not have the same friendship with your brother, family ties last forever. So it’s a good idea to put him in the spotlight alongside your friend.
This leads to another question. If you have multiple best men (and this even pertains to the groomsmen), how do you line them up? You could choose the coveted spot right at your side by a coin toss, or in terms of “seniority.” This means, the first person standing next to you should be the person you’ve known the longest; this is undoubtedly going to be a brother, if you have one. If you have more than one older brother, you’ve known them both the same amount of time – since birth! Give the oldest of the older sibling seniority. Next, younger brothers and then friends in the order of how long you’ve known them can be lined up. Another twist is when the bride wants her own brother to be one of your groomsmen. If you’re not buddy-buddy, stick him at the end, but make him feel important by carrying your note cards or something. Don’t forget to give each an important role and responsibility in the wedding and thank them with a token of your appreciation, such as with personalized best man gifts suited to the personality of each.