Straight-laced Princeton University admissions officer Portia Nathan (Fey) is caught off-guard when she makes a recruiting visit to an alternative high school overseen by her former college classmate, the free-wheeling John Pressman (Rudd). Pressman has surmised that Jeremiah (Nat Wolff), his gifted yet very unconventional student, might well be the son that Portia secretly gave up for adoption many years ago.

Soon, Portia finds herself bending the rules for Jeremiah, putting at risk the life she thought she always wanted--but in the process finding her way to a surprising and exhilarating life and romance she never dreamed of having.