|Tina Fey||Portia Nathan|
|Paul Rudd||John Pressman|
|Christopher Evan Welch||Brandt|
When straight-laced Princeton University admissions officer Portia Nathan pays a recruiting visit to an alternative high school, she receives some news that catches her way off-guard. John Pressman, head of the school and Portia's former college classmate, has surmised that his student, Jeremiah, is the son that Portia secretly gave up for adoption. Portia puts her career at risk by bending the rules for Jeremiah but also discovers a life and romance she never imagined.