When Catherine, a 40-something, single, and highly successful academic returns to her hometown to take care of her ailing mother, she reconnects with her college roommate and best friend, Gwen, now a stay-at-home mother and housewife married to Catherine's old flame. Both women, coveting each other's choices, attempt to find the happiness and fulfillment they lack by travelling a very bumpy road not taken, with surprising and hilarious results. This fast-paced, witty comedy by Gina Gionfriddo explores the continuing fallout and evolution of the feminist movement.