Charlie Plummer as Miles "Pudge" Halter, a new high school junior at Culver Creek Academy from Orlando, Florida Kristine Froseth as Alaska Young, the girl who catches Pudge's eye when he arrives at Culver Creek Academy Denny Love as Chip "The Colonel" Martin, Pudge's roommate and friend Jay Lee as Takumi Hikohito, Alaska and The Colonel's friend Sofia Vassilieva as Lara Buterskaya, a girl that Alaska sets up on a date with Pudge Landry Bender as Sara, The Colonel's girlfriend and later ex-girlfriend Uriah Shelton as Longwell Chase, one of the wealthy kids known as the Weekday Warriors as they were able to go home each weekend Jordan Connor as Kevin, a member of the Weekday Warriors Timothy Simons as Mr. Starnes, aka "The Eagle", the headmaster of Culver Creek Academy Ron Cephas Jones as Dr. Hyde, an elderly religions teacher at Culver Creek Academy