Straitlaced Princeton University admissions officer Portia Nathan (Tina Fey) is caught off-guard when she makes a recruiting visit to an alternative high school overseen by her former college classmate, the freewheeling John Pressman (Paul 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.

Kay and Arnold are a middle-aged couple whose marriage has declined until they are now sleeping in separate rooms and barely interact in any meaningful loving way. Finally, Kay has had enough and finds a book by Dr. Feld which inspires her to sign them up for the Doctor's intense week long marriage counseling session. Although Arnold sees nothing wrong with their 30 year long marriage, he reluctantly agrees to go on the expensive excursion. What follows is an insightful experience as Dr. Feld manages to help the couple understand how they have emotionally drifted apart and what they can do to reignite their passion. Even with the Doctor's advice, Kay and Arnold find that renewing their marriage's fire is a daunting challenge for them both.

Believing the quote that you are born alone, die alone and everything else is an illusion, George doesn't see the point of life, school, or homework. Then he meets Sally and he now has a reason to go to school and make friends, even if he's not ready to admit to himself or to her that he likes her. The school's principal and art teacher introduce him to an alumni, and successful artist, Dustin, who can help guide George along life's path, but other distractions start surfacing, and George might not even be able to graduate from high school.