I think in real life, all teenagers feel undefined, at least at some point. Because that's what being a teenager is about - the point in your life where you define who you are going to be in a myriad of different ways. And teenagers to this by experimentation - is this who I am? Did I try that? Did it feel right? Maybe I should try something else?
So for Will, who still has to define himself, the other teenagers that have settled on a definition are the most compelling ones. It lets him experiment about who he wants to be. And have direction in a way that he doesn't
This possibly also explains why Chelsea becomes so compelling in branches where she gets access to the masks. While Chelsea has defined herself, there are more than enough hints that she's lied to herself, and has shaped herself more around the expectations of others. The masks, for her, are a chance to escape and redefine herself
Contrast that to Patterson, who uses the masks as an extension of his defined self when he gains access to them
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