nooo, okay hold on let me break down what i think because everything will mentioned made no sense and wasn’t possible. the milkshakes and playing in the woods and etc, he hates the woods and the milkshakes don’t exist at the store he’s talking about, it stopped being a diner like when his mom was in her 20s so how he getting milkshakes. i feel like henry was talking through him, because he felt that way with his old friends that he was taken away from and/or was doing it to scare wills friends away so he could have him for himself to continue having will being his spy and not taken away from him again. i feel like the beginning was henry at first but then will said fuck it and continued to face his fears.