Casey Affleck portrays Jim, a disenchanted 27-year-old writer who escapes his modest beginnings in Goshen, Indiana, chasing dreams in the relentless city. After two years of struggling as a dog walker, his aspirations remain out of reach, compelling him to return to his parents' unassuming home.
His 32-year-old brother Tim (Kevin Corrigan), recently divorced and a father of two young girls, faces a similar fate, moving back after his business endeavors fall flat. Now, he works alongside their father Don (Seymour Cassel) and mother Sally (Mary Kay Place) at their family-run ladder factory.
Everything changes for Jim when he meets Anika (Liv Tyler), a warm-hearted nurse in a local bar. Their serendipitous encounter ignites an intense night, leaving Jim raw and exposed. A discussion between the brothers about whose life is more miserable leads to a fateful accident for Tim.
As Tim battles for his life in a coma, Jim confronts the stark realities of his own discontent. Grudgingly, he steps into Tim's responsibilities at the ladder factory, including coaching his nieces' basketball team, which has yet to score in 14 games, and faces the girls who are grappling with their father's dire situation.
During his visits to the hospital, Jim reconnects with Anika, evolving their bond further. But the revelation that Anika is a single mother compels him to reassess his life priorities. Despite the complications, Anika becomes Jim's unwavering support as he navigates the tumultuous waters of existence.
At the factory, Jim encounters his uncle Stacy—affectionately known as Evil (Mark Boone Junior)—who imparts unruly wisdom on topics ranging from intimacy to recreational habits. Inexplicably, Evil requests Jim's assistance with some financial dealings, including opening a checking account for what he claims to be a stash of family gifts amounting to $4,000.
Meanwhile, a dramatic turn unfolds when the DEA arrests Sally, Jim's mother, under suspicion of using the family store's FedEx account to smuggle drugs. The magnitude of the situation dawns on Jim as the mysterious villain behind it all warns him that any attempt to expose him would lead to Jim's own incrimination. Sally, the unwavering optimist, finds herself in good company among other inmates, cherishing a novel Jim sends her way. After a while, she is released on bail, but the shadows of her troubles cast a lasting impact on Jim.
Amidst his mother's incarceration, Jim wrestles with feelings of guilt over the chaos surrounding him. Despite his reluctance, Anika encourages him to seek joy, gradually breaking through his despair. Their relationship flourishes, prompting Jim to suggest that Anika and her son join him in New Orleans, symbolizing his hope to escape his predicaments. Yet, after some contemplation, the idea seems increasingly unattainable.
Ultimately, Jim decides to make the journey to New Orleans alone, leaving behind a heartfelt letter for his parents, promising never to underestimate their love again, while also revealing the drug dealer's identity. As chance would have it, Anika arrives at the bus station moments before Jim, only for him to turn back with luggage in hand, requesting to return to his reality. As the credits roll, Jim finds himself in the back seat, finally indulging in a much-anticipated bottle of water, a moment of respite courtesy of Ben's unexpected kindness.
