The Lesser of Two Evils: Choosing My Best Man

best man

Out of the many things to look forward to when planning a wedding, it seems like picking out your best man and groomsmen might be at the top of the list. Who doesn’t relish the opportunity to let a bunch of people know that while they’re really good friends, they aren’t quite as good of a friend to you as this one particular guy is? It’s an easy way to let people know where they fall on your friendship spectrum. And yet, that enjoyment was ripped away from me six years ago when my oldest brother decided to make his two brothers co-best men in his wedding. That pretty much locked in myself and the middle brother to doing the same co-best men thing when we eventually get married. Apparently it’s now a family tradition or something.

While I don’t really get an opportunity to select the identity of my best men at this point, I can still have some fun with these two guys who repeatedly tortured me for the past 30 years. Remember, only one person gets to stand closest to me on my big day. And that’s a lot of responsibility for that person because he’s a heartbeat away from being the groom. It’s a very important decision….which brother gets to marry my fiancee if I drop dead at some point during the seven-minute wedding ceremony.

So with that importance in mind let’s break it down with an old school Pro/Con list (note that names have been removed so as not to incriminate these guys for all of their past misdeeds, some of which were legitimately criminal).


Brother #1

  • Shoved my head into a wall/piece of furniture twice as children that resulted in two emergency room visits and two total stitches.
  • On New Year’s Eve one year, I was hitting it off with a girl whose inhibitions were severely lowered. After a brief make out session, I excused myself for the bathroom. Five minutes later I can’t find her anywhere…searching the area where I left her, searching the bar, searching the dance floor…oh there she is grinding away with my brother, who looks at me as if he hasn’t seen me hitting on this girl all night and gives me a big smile and thumbs up!
  • For more than 10 years, every time he got paired up on a sports team with me he publicly stated how he’d rather be forced to play alone than have me on his team. I’m still not sure he knows how insulting that is.
  • In that same vein, he repeatedly chose to play Legos by himself when we were kids instead of playing with me.
  • Tends to “wing it” for big speeches which turns him into a GIANT wildcard for a wedding.

Brother #2

  • Picked a fight with me during a fantasy baseball draft (because his internet got disconnected and he missed his pick) that caused me to have to walk one mile back to my apartment with a torn ACL. I never got an apology.
  • Once stole a Boston Bruins hockey puck that I owned and secretly got it signed by Adam Oates. He gave it to me as a gift, but a few years later he decided that since he got the autograph, he was suddenly entitled to the puck as much as I was. The puck disappeared a long time ago, and he pretends to not know where it is, but he says it with the same amount of conviction as that dad who pretended not to know where his son was when Nancy Grace announced on live TV that the son had been found in the dad’s basement.
  • Has cheated in every sport, board game and any other type of competition that I’ve ever been involved in with him.
  • Repeatedly tricked me into wearing ridiculous outfits when we were growing up. Off the top of my head, there was the matching Miami Dolphins mesh half-shirt and zubaz spandex shorts, and the most embarrassing moment of my childhood…showing up to a family party wearing my jean shorts backwards like Kris Kross. If brother #1’s preference was physical warfare, brother #2 dominated me in the psychological warfare category.
  • Will definitely be out for revenge after I delivered what many have called the greatest best man speech of all time at his wedding.


Brother #1

  • From ages 6-14, he listened to me babble on and on every night while we were trying to fall asleep in the same room. While it was always clear he had no interest in humoring my need to have girl talk, at least he didn’t turn into a complete dick about it.
  • Put out a significant fire I accidentally started in our bathroom 8 years ago. Had he not noticed & extinguished this fire, I have a feeling my life would be drastically different than it is right now.

Brother #2

  • I believe he holds a picture of me naked curled up in a piece of my parents’ luggage.
  • If not chosen as the primary best man, he’s very likely to hijack the microphone at the wedding and tell stories of all the weird sexual things I used to make The Simpsons action figures do to each other when I was in middle school, not to mention a full history of the many romantic novels I attempted to write around that same time in my life.

Tough decision, right? Many of you are probably even wondering, “Why pick either of them? They both sound like assholes.”

Duly noted.

I’m tempted to give brother #2 the nod due to the world of embarrassment he could unleash at any time, but I’m picking brother #1 for two reasons. First, because that fire he put out really did save my life. And second, because his swooping skills from that New Year’s story (not an isolated incident, by the way) make me think the wedding wouldn’t skip a beat if I dropped dead. Hell, he might even swoop while I’m saying my vows. I kind of like this wildcard being the second most important person at the wedding (besides me, of course).

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