Jack and his pals are NYC bachelors in their super-late 30’s who have spent two decades chasing women and fleeing commitment. When a childhood friend’s sudden tragic marriage shakes up their world of sex and booze, Jack realizes he just may be ready to commit to the one woman hopelessly out of reach.

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 Determined to confront the outdated mores of society and the institution that embraces them, Katherine inspires her traditional students, including Betty and Joan, to challenge the lives they are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.