I think it depends what you talk about.
Do you talk about everyday things... what you've both been doing,where your going out next, your family etc... or does he mention relationships he's been in, how they worked out, what went wrong and so on.
Maybe he just feels at ease with you.
Most of us have someone that we have as a friend who we know we can say what ever we like, whether it be advice on the latest guy/girl friend, or just something simple like, could I wear this dress with these shoes etc...
He could be leading up to asking you out, just wants to get to know you first,listen to what he says and take your lead from him.
However, if you choose to speak up first by asking him out and that is not his intention, then you may spoil what you have as friends.
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