Years ago, Portia Nathan (Fey) quietly placed her newborn son up for adoption. These days, she's got a great career recruiting students for Princeton University. Then, one day, Portia receives an unexpected call from her free-spirited college classmate John Pressman (Rudd). John runs an alternative high school that's home to some very gifted student. One such student is Jeremiah (Nat Wolff). John believes that Jeremiah could be the son that Portia gave up for adoption back in her youth. Meanwhile, as Portia puts her career in jeopardy by altering Jeremiah's transcript, an unexpected romance begins to blossom..