Ok... this post is hard for me to write. You see, it forces me to admit that I can be a complete doofus at times. Except for right now, because these are all in the past, and I never do anything wrong now. Now with that out of the way, let's talk about the singular most cringe-worthy thing you've ever done in-game.
For me it was five years ago when I was going to go and form a new guild. There was a really nice guy that ran my guild previously, and then handed the reins over to me. He wasn't around much after the transition, but eventually came back and wanted to take things over again. Enter awkwardness and a recipe for guild drama.
So a few of us are sitting around Vent one night going over how this new guild was going to distinguish itself. This was back in the day, mind you, and guilds were a lot more important then they are now. We had to have an identity and a strong force, or else we were just going to get washed over by the other guilds on the server. This was exactly what we were talking about, with a fair amount of alcohol involved, of course. We wanted to know how we were going to "fix the failed leadership of the past" and "avoid the mistakes that had been made." You'd think we were talking about Richard Nixon.
Into the Vent channel pops the guy that we're leaving over.