Act One

Six-year-old Jen Tracy welcomes her newborn brother, John, into the world with a warning about the way that things work and a promise to protect him from Dad ("Prologue / Welcome to the World"). As they grow, Jen does her best to shield John from life's disappointments, including a painful Christmas Eve fight between their parents ("Christmas 1"). Not long after John's seventh birthday, Jen discovers a bruise on his face. "It was my fault," he tells her, "I broke a glass." Jen vows that Dad will never hurt John again, and she and John make a deal always to be there for each other ("Think Big"). As Jen grows older, she becomes more interested in boyfriends than in brothers ("Trouble with Men"). But, when it's time for Jen to go off to college, John begs her not to leave him alone ("Hold down the Fort"). Jen is determined to break free, however, deal or no deal. "I can't hold your hand forever," she tells John. "Grow up."

Jen embraces the world of the '60s in groovy New York City, where she blossoms into a drug-dabbling hippie, while John's life goes in the opposite direction ("Timeline"). Without Jen there to protect him, John falls under his father's influence and decides to join the Navy ("It Took Me a While").

When Jen returns home from New York, she and John see how much they've changed and how far apart they've grown ("Out of My Sight"). Learning of Jen's plans to move to Canada with her draft-dodging boyfriend, John accuses her of rejecting everything he and Dad stand for, and they part in anger ("Run and Hide"). After John leaves, Jen unfurls an American flag, drapes it over a coffin and reveals that John has been killed in Vietnam. "I'm sorry, little brother," she whispers as Act I ends. 

Act Two

Now living in Canada 26-year-old Jen is the mother of a newborn baby boy, whom she names John ("Old Clothes"). But this John is not the naîve child of the '50s whom his mother expects him to be. When Jen moves back to the United States, leaving her failed marriage behind, she prepares to spend Christmas alone with seven-year-old John. Her gift to her son is an old baseball glove, which she proudly tells him belonged to his uncle. But John rejects the gift, complaining, "I'll be the only kid in school with a crappy old glove!" ("Christmas 2").

Jen gets her son to play his uncle's favorite sport, but her obnoxious behavior at games only succeeds in morifying him ("Little League"). Visiting her brother's grave on what would have been his 32nd birthday, Jen remarks on the similarities between the two Johns and vows that she won't fail her son ("Just Like You"). But when it's time for the twelve-year-old to go off to camp, Jen finds herself barely able to say goodbye ("Bye Room").

In a montage spanning John's high school years, John and Jen take turns as mock talk show hosts, covering topics that reveal Jen's growing dependence on her son and John's struggle for freedom ("Talk Show"). Later, when John discovers that his mother has hidden his acceptance packet from Columbia University, it becomes clear that Jen is terrified that she'll lose John "again," and she is no longer able to differentiate between her brother and her son ("Smile of Your Dreams")

Finally realizing how desperately his mother needs him, John decides to forgo Columbia in favor of a local community college ("It tooke Me a While – Reprise"). Disturbed to see him changing his plans for her sake, Jen ridicules his decision. John is deeply hurt by his mother's reaction and he bitterly mocks her influence on his life ("Graduation"). As their argument escalates, Jen slaps her son.

Shaken by the parallels to her abusive father, Jen retreats to her brother's grave, where she finally accepts that it's time to move on ("The Read Ends Here"). Jen returns home, where she asks John's forgiveness ("That Was My Way"). Jen is fianlly able to let her son go, and they take their first steps into the world on their own ("Every Goodbye Is Hello").