1995. A crowded auditorium. Author Louis Goldstein, mid-30s, is reading from his best-selling tell-all family memoir Goldstein to a large, enthusiastic audience. The book is a hatchet job, tracing his family’s story over 90 years, but showing them in an unflattering light. He reveals what he deems his family’s shameful secrets. During the reading, the spirits of his family, dead and living, come back to refute what he has written about them (“They Are Here”).

Louis’s elderly and ailing Aunt Sherri is in her hospital room with her niece— Louis’ sister Miriam. Sherri calls the book a pack of lies, and wonders where Louis got all of what she considers to be inaccurate information.

Back at the reading, Louis begins the multi-generational story of Goldstein, with his then 19-year-old grandmother Zelda’s journey from Russia to America. On the boat, Zelda meets and falls in love with a young and handsome "Man on the Boat." The two dream of a new start together in a new land (“Up Ahead”). The Man on the Boat promises to send for Zelda once he’s settled in America.

Zelda arrives in New York and lives with her brother and his cruel wife Irene. Zelda waits to hear from the Man on the Boat, but no letter ever arrives. Broken-hearted and desperate to escape from Irene, Zelda meets and marries Louie Rudolph. Together, they open a dress shop in New Jersey. Zelda keeps the story of her lost love a secret from Louie. Louie also has a secret: he deserted from the army during World War I. Upon the birth of their first child, Sherri, Louie confesses to Zelda, explaining that his real last name is Goldstein. He tells Zelda that, to start his new life in an honest way, he must turn himself in to the authorities. He assures Zelda that, despite the secret of his false name and desertion, he remains the good and reliable man she married (“I’m Still Me”). By the time he is released from jail a year later, his world has changed: the couple’s second child, Nathan, has been born, and Zelda has come into her own as a businesswoman. From now on, Zelda will be calling the shots.

It’s 12 years later, and Sherri and Nathan playfully make fun of their parents’ dubious business practices (“Honest As The Day Is Long”). Sherri, now a young woman of great academic promise, tells her mother that she’s been accepted to medical school on a full scholarship. Her parents, stuck in their old ways, do not approve, preferring that Sherri find a husband. Sherri pleads her case to Zelda (“When We Look Back”). Zelda ultimately defers to Louie— knowing that Louie will forbid Sherri’s request. Louie suffers a heart attack, and Sherri agrees to stay home and help in the store.

Sherri meets and falls in love with Sammy Leftofsky, the butcher’s son from down the street. Sammy leaves with Nathan to join the Navy and fight in World War II. Sammy and Sherri profess their love and promise to write to each other while he is overseas fighting (“Tell Me All”). Sammy dies in the war, leaving Sherri devastated. To comfort her daughter, Zelda shares the story of her own lost love— the secret story of the Man on the Boat. Zelda makes Sherri promise not to share the story, and Sherri agrees.

Nathan returns from the war despondent and broken. As an officer in the Navy, he was charged with incompetence of leadership during an incident that led to the death of several sailors, including Sammy. Feeling deep guilt, Nathan considers suicide, but is rescued from his despair by Sherri. Seeking a new start, Nathan decides to go to become a doctor. Upon his acceptance to medical school, his proud parents rejoice. While outwardly encouraging, Sherry privately resents her less-talented brother becoming a doctor (“Boys”).

Nathan marries Eleanor, a woman as strong in determination as Zelda. Despite protests from Zelda, Eleanor and Nathan move to Manhattan. Louie dies. Eleanor gives birth to Louis, named after his recently-deceased grandfather. Nathan takes his family to New Jersey each weekend to visit his mother Zelda, but Eleanor quickly tires of visiting her mother-in-law (“Visiting Your Mother”).

Zelda’s nemesis from her first years in New York, the mean-spirited sister in-law Irene, has died. When cleaning out Irene’s apartment, Sherri discovers a box with Zelda’s name on it. Sherri brings the box to Zelda, now in her 70s. In the box are letters from the Man On The Boat— letters Irene kept from Zelda 50 years ago. One by one, Zelda reads the letters (“Beloved”).

It is now the early 1980s. Now a young man, Louis comes out to his family. Nathan, a successful psychiatrist, disapproves. His mother, Eleanor, fails to stand up for Louis. When his younger sister Miriam gets married, Louis complains that her wedding is a sign that their parents are more accepting of her than they are of him (“Have You Met My Parents”).

Nathan dies, leaving his unresolved tensions with Louis. The aging and ill Sherri, distressed at the news, experiences a hallucination. In the hallucination, Sherri sees Zelda and blames her mother for having ruined her life. Other family members appear and express their resentment to their parents. The parents, in turn, defend their actions (“For The Best”).

A few days later, Louis visits his Aunt Sherri in the hospital. She angrily confronts him about the veracity of his memoir. She demands to know where Louis got all his incriminating information. Louis explains that it was her— Aunt Sherri herself— who has told Louis the stories over the years.

Shocked into recognition of her own stories, Sherri begins to accept her family’s mistakes, and the gravity of their life-altering decisions. She despairs that her life was wasted. Louis, aware of the distress his book has caused his aunt, assures her that her life has been valuable, saying that, if not for her, happiness wouldn’t have come to Sammy, Nathan, and even himself. Sherri, now having confronted the truth, finally finds a sense of peace. She encourages Louis to make his own peace with his deceased father, Nathan. The family members, living and dead, reappear and sing of the importance of acceptance and reconciliation (“Sherri’s Reprise”). Sherri pleads with the still angry Louis to forgive his father. Surrounded by his imperfect but loving family, and sharing a gentle look with his father, Louis begins his journey toward forgiveness.