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Never played that myself, but Shiloh was the type of person who gave me immediate red flags even during Step 1, so I have very few positive thoughts about them.
Children can be manipulative and hurtful, just the same as adults. Their capacity for it is often reduced, but it can very much still exist. Shiloh very much struck me very quickly as the type of person who will say ANYTHING to maintain their position in the social hierarchy and would try to push others down that hierarchy to maintain their own position.
In short, manipulative. Honesty is the best policy, and Shiloh is not honest. Effectively ever. He even confirms as much later on, and is known as a constant perpetual liar in his home game, from what I have heard.
Xoxo droplets is a different game. It was one of the developer's previous games, and Shiloh and Jeremy both come from it. That game is, from what I know, about incredibly screwed up people in one way or another. From people like Shiloh who are completely manipulative bastards, to people like Jeremy who by that point seems entirely apathetic to life.
and i also got that feeling when later on, we meet him and he act like he doesnt know us
but idk? maybe he's just a lost child, that's all. i wish we had more contact with him, and become like a friend idk
Shiloh is extremely insecure from a young age, and gravitates early towards people with the strong personalities that he lacks. He is incredibly manipulative as he gets older, with some small signs of this as a kid, which stems from this lack of confidence. He's not ultimately bad, he just does what he can to avoid being hurt. The game hes from does better at getting this across.
As for who he has a crush on, it seems obvious to me it was always Lizzie, and he does seem to care for her genuinely when he's older. It's really sweet to see him overcome his issues and reconnect with the sunset bird gang in the later steps with the context of both games. The context makes scenes like seeing him while hes on his summer trip with JB and the group make so much sense.
I like Shiloh as a character personally, but then again take my opinion with a grain of salt. After playing XOXO Droplets I personally love Jeremy now, him and his punchable face.