Though never the picture of happiness, the Wilcoxes once seemed like a typical white Jewish clan from the Upper West Side. But in the early 2000s, two events ruptured the relationships between them. First, Naomi revealed to her children that her biological father was actually Black. In the aftermath, college-age daughter Bering left home to become a radical peace activist in Palestine’s West Bank, where she was killed by an Israeli Army sniper. Now, in 2018, Winter Wilcox is getting married, and her only demand is that her mother, father and brother emerge from their self-imposed isolations and gather once more. After decades of neglecting personal and political wounds, each remaining family member must face their fractured history and decide if they can ever reconcile.

Kelly Thorndike has just moved back to his hometown of Baltimore when one day an African American man he doesn't recognize calls out to him. Kelly is surprised to learn that this man is his friend Martin who went missing 20 years ago, and had been a white, skinny, Jewish boy. Martin tells Kelly of his racial reassignment surgery and asks Kelly for his help to spread the word. Kelly agrees, but things quickly sprial out of control.