Newly single, 35, and uninspired by his job, Jesse Fisher worries that his best days are behind him. But no matter how much he buries his head in a book, life keeps pulling Jesse back. When his favorite college professor invites him to campus to speak at his retirement dinner, Jesse jumps at the chance.

Katherine Watson is a recent UCLA graduate hired to teach art history at the prestigious all-female Wellesley College, in 1953. Determined to confront the outdated mores of society and the institution that embraces them, Katherine inspires her traditional students, including Betty and Joan, to challenge the lives they are expected to lead.