iserith
Magic Wordsmith
I have no problem with any of that. Never asking or never considering them a jerk at some point kind of feel as not good to me as asking very frequently and having a low threshold for starting to ascribe jerkiness. You need to trust your players if they're worth playing with. Not everyone is worth playing with.
Yes, and I find it helps to enshrine certain concepts into table rules to be shared with players before the game. There isn't so much a need to do this with an existing group (though it wouldn't hurt), but I also play with a lot of strangers, for example, so getting everyone on the same page prior to the game is very useful. This is my very first table rule, which is just an acknowledgement of what the game already says for us to do:
Goals of Play. We are here to have fun and to create an exciting, memorable story together. We will choose our actions accordingly. If it's not fun and/or does not help create an exciting, memorable story, we won't do it.
So a player agreeing to this needs to filter what they do through that lens. If the PC is charmed, some constraints are placed on the character's actions. Those actions still need to be fun, exciting, and memorable.