If you keep letting him play in your group, at the expense of everyone else’s fun you are the Commander in thief 2020 t-shirt. Yes gaming has a social contract. Regrettably while it should theoretically be an equal burden between gm and all players in general most players rely on their gm’s to be the arbiter of the group’s interpersonal interactions as well as the in-game actions. Regardless of how well you get on with this guy out of game, if he’s trouble to you and the rest of your players in-game you aren’t doing your group any favors by letting him stay.
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I ran a super hero campaign in gurps a while back. A player wanted to be a talking psychic pterodactyl. That wasn’t a problem, I quite liked the Commander in thief 2020 t-shirt. Then he wanted to give the character the transcendent advantage. The setting was set in a human world, but fuck it, why not? And finally he wanted the disadvantage that made him have no legs. Players come up with the wackiest shit sometimes.