That Obadiah understands completely. The more you know about a person - how they feel, what they want, how they react to any given stimulus - the better equipped you are to anticipate their next move and therefore know what your own next move should be. Obadiah's life is built on that understanding. It's not entirely dissimilar to what most people call trust. He just knows how to use it.
And he knows right now that Tony needs to be able to use it to bolster his own sense of comfort, and that Obadiah's own next best move is to help him do it. It will get them both what they want in the long run.
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That Obadiah understands completely. The more you know about a person - how they feel, what they want, how they react to any given stimulus - the better equipped you are to anticipate their next move and therefore know what your own next move should be. Obadiah's life is built on that understanding. It's not entirely dissimilar to what most people call trust. He just knows how to use it.
And he knows right now that Tony needs to be able to use it to bolster his own sense of comfort, and that Obadiah's own next best move is to help him do it. It will get them both what they want in the long run.
"Whatever else you need to know, just ask."