Boo is a teen struggling with depression and troubles at home and school. When Boo encounters Simon one evening, Simon makes him a wager with a chance to win his custom designed skateboard. As Boo practices on the skateboard he begins to find a semblance of joy that is foreign to him.

Simon reclaims his skateboard but gives Boo one more chance to win a board from him. Boo's father learns of his desire to start skating and refuses to let Boo keep his new board.

Dr. Bell wants to help Boo improve his mental health by taking an active interest in Boo's desire to learn to skateboard. To protect his privacy, Bell introduces herself as Boo's sister to Simon, who offers to teach Boo to skate in exchange for Bell's phone number.

Simon prepares for one of the biggest challenges of his skating career while also coaching Boo in his own journey of learning how to skate.

After Boo's father learns that he has been sneaking off to go skating, Boo ditches his father to watch Simon skate at Giant's Court.

Dr Bell discovers that Boo has returned his skateboard to Simon and left him a concerning letter. Bell immediately contacts Boo's father to warn him of her fears that Boo may be contemplating suicide.

Boo takes an opportunity to face his old friends once more at their showcase.