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RyanGosling as Dan Dunne
Shareeka Epps as Drey
Anthony Mackie as Frank, a local drug dealer
Monique Gabriela Curnen as Isabel, a teacher
Starla Benford as Principal Henderson
Karen Chilton as Karen, Drey's mother
Deborah Rush as Jo Dunne, Dan's mother
Jay O. Sanders as Russ Dunne, Dan's father
David Easton as Jeff Dunne, Dan's brother
Collins Pennie as Mike, Drey's brother
Dan Dunne is a young history teacher at a Brooklyn school, with a teaching style that rejects the standard curriculum in favor of an approach based upon dialectics.
Though he seems to have it all together in the classroom, in his own time he is found frequently snorting and freebasing cocaine. But after a basketball game, Dan's ex-girlfriend, Rachel turns up, evoking emotions that he cannot handle. A short while later, one of his students (and a player on the girls' basketball team he coaches), Drey, catches him getting high in the locker room. The compromising situation propels a binding friendship as Dan would prefer not to lose his job and Drey feels sorry for him.
Drey has to deal with the negligence of a single-mother who is always at work, a brother, Mike, who is in prison for selling drugs for neighborhood dealer, Frank and an absent father. Drey's lack of supervision makes her a target for Frank's operation and he encourages her to become involved in his business.
As Dan and Drey begin to get a better understanding of each other as friends, they both know what the other one should stay away from and what they need, but is struggling to get by themselves. Dan perceives that Frank is a bad influence on Drey and tries to intercept on numerous occasions. And Drey tries to get Dan to open up about his drug habit to no avail as he feels uncomfortable talking with a student about it.
After a tense conversation with Frank about Drey, Dan goes to Isabel's, with whom he had a previous date and forces himself on her, but she defends herself and runs off, he feels bad and decides to leave. The following day, he further takes his stress out on Drey, telling her to talk to friends her own age when she finds him, hoping to hang out. Drey, a little upset at this, is pushed further into the company of Frank, and he has her do her first drug deal.
Dan goes to his parents' house for dinner, where his brother, Jeff, and his girlfriend, Cindy, also attend. He says little, and does not enjoy himself much, but a joke of Jeff's that Cindy tells him makes him laugh. The same night, Drey is out with Frank, dealing. Drey arrives at a place to deliver some drugs and is surprised to find that she is dealing to Dan amidst a group of friends also getting stoned. The next day, Dan is not at school, and his students are told that he is being replaced by another teacher. This changes something within Drey as she refuses a lift home from Frank, choosing to turn from that path.
She knocks on Dan's door and he answers. He goes into the bathroom, shaves and cleans himself up, before sitting down to drink a glass of water.
Drey sits down and joins him.
RyanGosling as Dan DunneShareeka Epps as DreyAnthony Mackie as Frank, a local drug dealerUS">Monique Gabriela Curnen as Isabel, a teacher
Starla Benford as Principal HendersonKaren Chilton as Karen, Drey's motherDeborah Rush as Jo Dunne, Dan's motherJay O. Sanders as Russ Dunne, Dan's fatherDavid Easton as Jeff Dunne, Dan's brotherCollins Pennie as Mike, Drey's brother
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