Henry definitely didn’t know about Ashley until Emma showed up because when Emma discusses Ashley in Price of Gold, Henry’s response and input is as if it is new information to him.
Also, Henry doesn’t seem to have many close school friends, which has been referred to several times over the course of the show. He certainly had acquaintances but not friends that he hangs out with or has playdates with. When he was younger, he likely just didn’t notice other kids stayed the same age. Now that he is older, he has started to notice and question it, especially since he got the storybook.
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