I wonder if the scene will take place in adult Henry’s mind, with Jared playing the part of Henry’s subconscious, the youthful idealism and optimism that adult Henry has forgotten. Accepting that side of himself could be the last step toward breaking the curse — or rather, having already broken the curse, recovering from it.
On the other hand, Henry has an inferiority complex (as seen in 7×16 “Breadcrumbs”) concerning his childhood role models that leads him to make bad decisions. He needs to have a conversation about that with his younger self.