Wilson, portrayed by Woody Harrelson, is a lonely, neurotic middle-aged man residing in Minnesota, where he shares his meager existence with his one true companion, his dog, Pepper. Having lived for seventeen long years in the shadow of his past, Wilson remains haunted by the choices made by his ex-wife, Pippi. Their relationship crumbled after Pippi, yearning for a different life, not only aborted their child but also slipped into a web of prostitution and drug use, leaving Wilson to grapple with the remnants of his shattered dreams and aspirations.
Wilson's already bleak life takes a turn for the worse when his friend Robert, played by Brett Gelman, relocates to St. Louis, Missouri, with his wife Jodie, acted by Mary Lynn Rajskub. The move is clearly a decision influenced by Jodie's disdain for Wilson, who is left without a single true friend in a tiny apartment that echoes with solitude. Feeling increasingly isolated, Wilson contemplates the state of the human experience, lamenting that society has entirely forgotten the meaning of community and the joy of connection with friends and neighbors. In his discomfort, he often broaches the subject of his father's stage four lung cancer with complete strangers, laying bare his vulnerability in a world where social norms have become awkward and strained.
As fate would have it, Wilson learns that he must journey to see his father, who has been diagnosed with terminal cancer. With a heavy heart, he leaves Pepper with the dog sitter, Shelly, as he braces himself for what lies ahead. Sadly, when he arrives at the hospital, all he can hope for is a display—any display—of emotion from his father, only to witness his passing instead. Emotionally unmoored, Wilson is left with the task of arranging his father's funeral and sorting through the remnants of a life that once held meaning.
In a twist of irony, he encounters an old school friend, Orson, played by David Warshofsky, who serves as a reminder of the shared memories of their youth. But instead of comfort, Wilson finds Orson's toxicity unbearable, remarking that he is nothing more than a soul-sucking vampire. Desiring to find connection once more, Wilson confesses his wish to date again, but Orson, unencumbered by relational desires, dismisses the idea. In an attempt to find companionship, Wilson bumps into a woman at a pet store, only to botch the encounter entirely by inadvertently rear-ending her vehicle, making a fool of himself as her daughter points out his clumsiness.
Later, he meets a woman named Alta, portrayed by Margo Martindale, at the supermarket, and over their conversation, he reminisces about his ex-wife. Alta suggests that Wilson should use a People Finder application to track down Pippi, reigniting hope within him. With Alta's assistance, he manages to locate Pippi's sister, Polly, and soon discovers that Pippi has made her way back to Los Angeles.
Determined to find her, Wilson embarks on a quest that leads him to Pippi, played by Laura Dern, who is trying to rebuild her life as a waitress. Their reunion is initially fraught with tension, but as they begin to reconnect, Pippi reveals a shocking secret: she didn't abort their child after all—she gave their daughter up for adoption. This revelation prompts Wilson to track down Claire, their daughter, navigating a complicated relationship with her as they bond over shared experiences.
The journey isn’t without complications. As Pippi and Wilson continue to get to know Claire, played by Isabella Amara, Claire grapples with her identity and her adoptive family's disinterest, causing friction throughout their interactions. A visit to Polly’s suburban family takes a dark turn, leading to a catastrophic falling out that ends with Wilson facing a long prison sentence. Inside, he struggles but gradually finds a way to win over his fellow inmates with his honesty and charm.
After serving a grueling 36 months, Wilson is released, only to find a drastically altered world; his favorite haunts are closed, and tragically, he learns that Pepper has passed away in his absence. Returning to Shelly, his former dog sitter, he looks for comfort in the aftermath of his losses, and their relationship takes an unexpected turn as they begin to date.
The twists keep coming as Claire reaches out, revealing she is pregnant. Despite her adoptive parents' disapproval, Claire ultimately decides to incorporate Wilson into her baby's life, signaling a new beginning for him. In the end, Wilson finds a path through the chaos, experiencing joy once more, alongside Shelly and their new dog, crafting a semblance of family amidst the disarray of his life.
