I enjoyed this section, too, and thought that it could play pretty well as a short story.
What appeared (to me, who's never read IJ or knows anything about the specifics of the plot or character) to be happening is that the conversation starts as a conversation but at some point Hal retreats into his head, merely thinking his half of the conversation with Himself continuing to talk about.
As for the reveal that the Profesional Conversationalist is Himself, that, to me, spoke to not only the relationship between Hal and Himself but also to some idea that Hal has perceptions of reality that aren't real. He's just seeing different things because he's thinking different things, if that makes any sense. It just never occurs to him at first that this guy is Himself.
Also, as for the Hamlet tip of the hat, this could easily be Hamlet's first encounter with the ghost. But, again, I'm not even sure where/how the Hamlet is going to play into this book and who/what/if anybody can be taken as character analogs.
_________________ First time reader.
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