I am in a game that has been running for about 2 years now, we had one DM-switch up but the story has continued and most PCs are the same. I am playing a human Bard/Warlock named Fleik and the DM of our main campaign said something during a oneshot run by a friend of ours that caught me off guard and kind of amused me.

Context doesn't really matter here, but he had laughed and said, "I just know Fleik really well." And I had laughed, because it's true. This DM knows my character so well, that I think he predicts most of my actions before I've done them. At first, I thought that maybe I'm just being basic, maybe my chaotic is not actually chaotic if he is predicting what I'm doing so well, but I have found that while I don't surprise my DM often, I do consistently surprise the other players at the table. This being said, this has happened over time. Fleik has a very close relationship with his Patron and considers his Patron his best friend. He has a constant link with his patron and this DM and I have done a lot of roleplaying of their conversations and shenanigans during down time between sessions. Fleik is a bit of a bleeding heart and doesn't actually agree with all of his Patron's outlooks, but still talks about himself and how he sees the world quite a lot. They don't argue per say, but they both certainly know where the other stands on most things. So this has given my DM lots of time working with Fleik and knows a massive about about how he thinks about the world, but I have been playing Fleik for 2 years and at this point, he is one of the best developed characters I've ever played.

I do DM myself, and I have never had a PC that I knew so well I could predict what they were going to do consistently. I've had a few that I could, but not so much because I knew the character, but more that I knew the player's play-style. Perhaps that is what this is, but my DM did say 'I just know Fleik really well' not 'I just now Caesyum really well', which I think is notable.

So that is my question for you: How well do you know your player's characters? Have you guys had a character at the table you think you knew almost as well as the player did? Or someone you could predict the actions of more than the usual 'I know their backstory and they hate guards so they are going to be aggressive in this encounter' sort of thing. Tell me about them, I'd be interested in hearing about who and how and why you knew/know these characters

I make it a point of not knowing my players’ PCs that well so that I am surprised when they respond to the challenges that I present them with. That also prevents me from tailoring adventures too much for them so sometimes Chloe,Engels that I expect to be hard end up being really easy. Which is a good thing, they’re heroes, they’re better than average. Some things should be easy. 

That's a cool outlook! Does this ever create the opposite problem of making things that should be easy being more of a challenge than expected?

I know my player's characters well enough to play them when they're gone. This is a frequent thing to happen in my games, so I make sure to notice exactly how they play their characters when they're gone so I can tell them what their character did during the game when they were gone, and more often than not, they say that how I played them was probably what they would've done if they were there.

Yes. It does result in outcomes that I wasn’t planning on all of the time. Which is fine, it’s a game and the goal is to have fun!

Pretty well: Playing the same group 30+ years, as a DM & PC