Simon's brow was in the constant state of up as he listened to the captain's..well, babblings seemed a little too feminine for the Brown Coat. The thought of it caused the doctor to cough, covering the laugh that dared escape. Right probably was not the right time to laugh at Malcolm Reynolds; actually, as far as Simon knew, it was never a good time for Simon Tam to laugh at Malcolm Reynolds.
"It's not about the Black, or being too comfortable. I'm not going to say I'm overly happy here, captain, but River seems to be finding her way." Even if it is with a psychopath. "And, from what I understand it is impossible to leave if the City doesn't want you to. It provides for you. Well, for most people, I don't know what it will do for you." There was the smug smile, but he had meant it as a joke, honestly.
"But, if you can get free, I think it would be wise for River and me to be moving along. I've seen a few Blue Sun posters, and I know at least one person has attempted to take her life. While Alliance might not be here, she still isn't safe." Ever one to look out for his little sister. Then again, out in space, Simon didn't seem so out of place - something he never thought he'd consider.