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Talking to Himself: Takeshi and the Kid, which happens in the prologue and the end of the game, but is otherwise averted due to them having no voiced lines in their own routes. The two Yous also go through this.
What Could Have Been: An earlier version of the ending CG for You's Route shows the person she's kissing as having blue hair. Given that the Kid's outfit in that ending is the same as Takeshi's original outfit (which was changed during development), it's possible that You was originally meant to be one of Takeshi's heroines, but was changed during production.