Every spring, high school seniors anxiously await letters of college admission that will affirm and encourage their potential. At Princeton University, admissions officer Portia Nathan (Tina Fey) is a gatekeeper evaluating thousands of applicants. Year in and year out, Portia has lived her life by the book, at work as well as at the home she shares with Princeton professor Mark (Michael Sheen). When Clarence (Wallace Shawn), the Dean of Admissions, announces his impending retirement, the likeliest candidates to succeed him are Portia and her office rival Corinne (Gloria Reuben). For Portia, however, it’s business as usual as she hits the road on her annual recruiting trip.
On the road, Portia reconnects with her iconoclastic mother, Susannah (Lily Tomlin). On her visit to New Quest, an alternative high school, she then reconnects with her former college classmate, idealistic teacher John Pressman (Paul Rudd) — who has recently surmised that Jeremiah (Nat Wolff), a gifted yet very unconventional New Quest student, might well be the son that Portia secretly gave up for adoption years ago while at school. Jeremiah is about to apply to Princeton.
Now Portia must re-evaluate her personal and professional existences, as she finds herself bending the admissions rules for Jeremiah, putting at risk the future she thought she always wanted — and in the process finding her way to a surprising and exhilarating life and romance she never dreamed of having.