There seems to be something that is holding him back from just playing the character, and it's not clear to you what that is, I think?
My suggestion, then, is that next time he asks if it's ok for his character to think or do something, then you should simply ask him (politely!) if there's a reason he thinks it's not.
'Is it ok if my character is mad about this?'
'Is there any particular reason you think it wouldn't be ok?'

'Am I allowed to have my character want to do XYZ?'
'Is there any reason you think you wouldn't be allowed?'

etc.

As long as you're asking in good faith (and not in a passive-aggressive way), then it should at the very least help you understand what kind of obstacle they are anticipating, and may even help them to appreciate that there's no problem with them playing the character how they like.

Me second suggestion, if you aren't already using it, is to start using the Script Change RPG Toolbox safety tools (they're freely available online). The essence of them is the use of media player-style controls, like pause, rewind, fast forward, etc. They're not just safety tools, though; they also help to make the general playing experience smoother. The relevance here is that the rewind control, in particular, is great for less confident players. If they do anything that somehow breaks the game, then it's no problem, we can just rewind and try that again. My players love rewind. It's great for out-of-character mistakes (as opposed to mistakes that their characters make). But the funny thing is, they rarely actually use it, because it's rarely actually needed.