Well I said I would report back so here I am. I had my first game with the new group. It was rather strange, as I'm not used to playing with newbies. My usual experience with gaming is with grognards, and the game very quickly gets into a rather smooth operation: go to the dungeon, kill the monsters, fetch the gold, bring it back for XP, rinse, and repeat. Roleplay is present but secondary, it's a game, not a narrative. The characters are tools for combat and exploration first, not people. It's just a different way of playing, is all.
Now, with the newbies coming into roleplaying after the Critical Role phenomenon, it's different. They all want to elevate their characters to some literary figure. I sat through a 10-minute argument between two players because they have PCs whose "personalities" clash. These players have pet characters that they intensely protect from all danger, to the point of being a detriment to the game itself. They don't want to go into the cave "because there might be something too dangerous inside." Well wtf man, that's the whole fucking point, is it not?
The DM is aware of the problem and was privately messaging me days before the session, telling me he was hoping that I would stir the other players to action. I have never had that happen to me before. Usually, DMs are control freaks who want to have complete control of the world and the players somewhat. This guy is apparently too afraid to be candid about the pet characters that are paralyzing his game and is trying to recruit me as his hatchet man.
Welp, I'm happy to inform you that I embraced the task. We saw some action and a character got killed, although it was an excruciating process that took several minutes of arguments. But before that, let me tell you about what we did in town before going out into the caves.
One of the players actually had his character looking for work AS A FUCKING BARISTA AT THE LOCAL INN! Holy fucking Christ Jesus, man. Here we have a game where you can be a hill giant, a devil, a paladin, a rogue, a demon prince from hell, or a fucking dragon if you want to. And this guy takes a 15-minute side quest to try and get his character work waiting tables! There was nothing particularly important about this inn, either. It's just an inn.
And it's not like we were short on money either. This is a Monty Haul DM and each of us had enough money to afford food and board for like a whole year. Besides, we can just hear
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