[There are a lot of people on the ship whose files he probably wouldn't have hesitated to read. He doesn't have a lot of moral qualms about invasion of privacy when it comes to the majority. A few people he does feel a sense of -- not exactly protectiveness of, per say -- but more respect for, perhaps, than others. And maybe his respect for Dean is misplaced because he was friends with the other version of Dean, or maybe it's because he can sense how deeply Dean's mistrust in everyone goes, but whatever it is, it's a courtesy he wouldn't extend to most.]

I honestly have no clue. My plans these days tend to be a lot more of the fly by the seat of my pants kind than anything.

[Mostly because he or someone close to him is in some kind of life-threatening danger and he doesn't have the time to really plan things out. He operates on instinct most of the time anymore. Sure once upon a time he'd had a ten -- and then a fifteen year plan of wooing Lydia Martin and ending up with some kind of happily ever after. He doesn't believe in that kind of thing anymore really.]