One night, at a seaside jazz café called The Summer Club, Jackie Sherman catches the amber eyes of a familiar stranger. Startled by the pull she feels toward him, she follows him out to the edge of the ocean, where he relays that in another life, she knew him intimately as her first love. Jackie, who has no memory of this man, is then presented with a choice: the opportunity to experience the entirety of her relationship with him compared with the life she chose as another man’s wife—and subsequently, the opportunity to choose a different course. Through a whirlwind of two passionate romances, the world of glitzy Manhattan wealth, and excursions to bustling Boston, elite Hyannis Port, and exotic Positano, Jackie must navigate the movements of her heart while pursuing her dream of higher education and a writing career as a woman at the cusp of 1950.