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I thought it was simply the person he was supposed to be while there, undercover, and all, wouldn't know any of this. this specific conversation), so he's trying to get a read on Howard by continuing the topic of Howard being Tony's father (unbeknownst to Howard at the time that he is speaking to Tony). Tony has a limited window on getting to know his father face-to-face (i.e. In this conversation, Tony has an opportunity to maybe find that out. Maybe he was, but the company unexpectedly took up more of his time than he was anticipating. Maybe Howard never was interested in children. This could help reframe Tony's opinion on Howard. Was he excited about it? Was he disinterested? Was he dreading the thought?
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To me, this scene reads like Tony is continuing the conversation about Howard's child, in an attempt to be able to read Howard's feelings about being a father. His business acumen is well documented, but Tony never really knew Howard as a father. By the time of Endgame, Tony has seen the video Howard left for him, so he knows that Howard did in some way notice Tony, but Howard is still a very incomplete image from Tony's past. Howard was much too busy with his company, and Tony wasn't really fathered much as a result. The main thing Tony remembers about Howard as a father is his absence.