As children, Sammy and Terry Prescott experienced a tragic loss when their parents were killed in a car accident. Fast forward a few years, Sammy, portrayed by Laura Linney, has become a single mother and a lending officer at a bank, residing in the familiar confines of her childhood home in the picturesque Catskill Mountains of New York. On the other hand, Terry, who has drifted across the country over the years, has faced his fair share of struggles and conflicts.
After a long silence between the siblings, Terry, alongside his girlfriend Sheila, finds himself in a financial bind and decides to visit Sammy and her son Rudy. Their reunion is filled with a mix of excitement and disappointment, especially when Sammy discovers that Terry was incarcerated for three months, which explains his lack of contact. Despite this revelation, she shows compassion and lends him the money he requires, which he sends back to Sheila. However, when Sheila attempts suicide, Terry chooses to extend his stay with Sammy, who welcomes the opportunity to reconnect with her brother.
In the midst of this turbulence, Rudy is tasked with a school writing assignment that leads him to envision his father, whom he has no memory of, as a magnificent hero. While Sammy has always painted a bleak picture of Rudy's Sr., Terry bluntly informs him that his father is far from a good man, a truth that Rudy naïvely struggles to accept. Throughout this period, Sammy finds herself rekindling an old flame with an ex-boyfriend named Bob, who surprises her with a marriage proposal after a brief courtship, leaving her to contemplate her future.
At her workplace, the new manager Brian introduces unconventional demands, which frustrate Sammy, especially when he insists she arrange alternative transportation for Rudy rather than allowing her to leave work spontaneously. Despite some initial conflicts, they begin an affair, even while Brian's wife is nearing the end of her pregnancy.
As the bond between Terry and Rudy strengthens, Terry tests Sammy's parenting boundaries, occasionally causing conflict by keeping Rudy out late to enjoy nights at the bar. Seeking help, Sammy turns to Ron, her church minister, for guidance on how to address Terry's life choices. The relationship between Terry and Rudy deepens, but Sammy also recognizes her own flawed decisions and ultimately rejects Bob's marriage proposal as well as her affair with Brian.
One day, filled with adventure, Terry and Rudy head to a trailer park to confront Rudy Sr. However, the encounter quickly escalates into violence when Rudy Sr. denies his fatherhood, leading to a fight where Terry is arrested after defending himself.
Returning home, Sammy must confront the truth about their family dynamics with Rudy. After an important discussion where Rudy asserts that Rudy Sr. isn't his father, Sammy tells Terry it's time for him to find his own path, despite how vital he has become in their lives. Although initially resistant to the prospect of moving out, Terry ultimately decides to pack up for Alaska. However, before he departs, they share a heartfelt reconciliation, accepting the reality of their lives and the choices that lie ahead.
