Jacob Pressley is seventeen years old, over-privileged and seething with anger. After getting in trouble with the police one too many times his exasperated parents decide that he needs a change of scenery, shipping him off to New York City to live with his sister for the summer and forcing him to attend regular sessions with a therapist. Jacob is determined to keep himself shut off from the rest of the world, but his perspective is slowly changed when he meets beautiful graffiti artist Samantha while also forming an unconventional bond with his psychiatrist Jane, two relationships that will teach him about both the brutalities of life and the unexpected realities of love.