In 2002, Dr. Frank Tassone (Hugh Jackman) is the superintendent of Roslyn School District in Long Island, which oversees Roslyn High School. Frank, along with his assistant superintendent Pam Gluckin (Allison Janney), have overseen major improvements in the district, with Roslyn becoming the 4th ranked public school in the country under their watch. The school's performance in turn stimulates the local economy, reaping rewards for school board head and real estate broker Bob Spicer (Ray Romano). Frank is beloved by students and parents alike, and sought after by women; Frank claims to have lost his wife several years ago, but is in fact a gay man in a secret relationship. While attending a conference in Las Vegas, Frank begins an affair with former student Kyle Contreras (Rafael Casal)...
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