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If you dig real hard and remove all the layers of pretend and coping mechanisms and the likes, Henry is, at his most base self, someone who is defined by a complete and utter inability to understand humans. He does not understand their morals (see: Panne, Ricken, Lissa’s supports) he does not understand how they emote (see: Olivia’s supports) honestly pick up any of his supports and you’ll find Henry baffling others in a way or another. His early life was filled with intense social isolation, what’s with “being raised by a wolf” and “abusive magic school of doom,” to the point where he finds it easier to understand animals or even plants over people (see: Cherche, Panne, Maribelle’s interlude) Even when he grows to like the Shephreds and actually actively tries to connect with them, his attempts are often met with failure (see: summer scramble, kellam’s interactions)

But the kicker! What makes Henry truly tasty!! Is that despite everything, no matter how inhuman, monstrous, beastly Henry may be, he is still a human, and “Henry does not understand humans” applies first and foremost to himself. Henry says a lot of shit he genuinely believes but that doesn't mean he is correct about his interpretation of himself. In his supports with Ricken that he’d be upset if Ricken died, and immediately afterwards admits that he has no idea why he would be. In the Summer Scramble dlc, he mentions that he cares for no god, but he does care for what Libra thinks of him, even though he doesn’t know why either. Henry is a hard person to figure out because himself doesn’t know what he’s feeling or why he does things half of the time.