Thomas Zelda, portrayed by Tim Allen, has just been released from prison after serving time for movie piracy. He is welcomed back by his quirky sister Viki, played by Sigourney Weaver, whose knack for bending the truth presents an unsettling backdrop for Tommy’s reintegration into society. Viki insists that her fabrications are well-meant, all to protect their family from harsh realities. Upon moving into her home, Tommy finds out that his grandmother had been led to believe that he was vacationing in France, a lie concocted by Viki. As she battles fragile health, Tommy feels compelled to uphold this deception. When Viki’s husband, Ed, inquires whether Tommy will head "back to France" soon, Tommy unwittingly agrees, unaware of the implications this euphemism will carry.
Things take a turn at a tense dinner when Gray, played by Ray Liotta, Tommy’s ex-partner in crime, unexpectedly shows up, leading Viki to chase him away. The next day, Tommy is summoned to meet his parole officer, Angela Popadopolous, portrayed by Jeanne Tripplehorn. She informs him that as part of his parole, he must work at "Pirate Burger," a pirate-themed eatery. Caught between the desire to follow in his father’s footsteps in painting and adhering to his legal obligations, Tommy faces tough choices.
As he adjusts to his new job, an unexpected reunion with Christy, his presumed-dead ex-girlfriend, throws Tommy’s world into chaos. Discovering that Viki had misled him about her fate, he is pulled into a whirlwind adventure with Christy, only to learn that she is engaged to someone else, Frank. This realization forces Tommy to retreat, leaving him to ponder the repercussions of his previous decisions.
Tommy next receives a surprising call, leading him to Angela’s apartment, where her son Ethan is scheming to help his mother find love. Upon seeing the untidy state of the apartment, Tommy decides to apply his skills and teams up with his ex-con pals from Pirate Burger to transform the place while Angela is away. Meanwhile, Tommy's fictional escapades in France continue, leading to a nonexistent romance with a French astronaut who sacrificed herself for the sake of Tommy's mother.
Angela's fury arises when she realizes Tommy has been in her apartment without permission. However, upon uncovering his altruistic motives, she refrains from pressing charges. Instead, she offers him a new painting assignment for a judge. As Tommy engrosses himself in this project, he finds himself being invited by Angela to support his case at a little league game, further deepening their bond. Unexpectedly, his work impresses the judge's wife, who requests additional painting.
Amidst these developments, chaos ensues as Edgar and Rick, in a moment of carelessness, displace the judge's wife's precious diamond ring. In an ill-conceived gesture of kindness, Edgar decides to steal it and present it to Christy as if it were a gift from Tommy. Unbeknownst to Tommy, this act sets him on a perilous path.
During the little league game, Tommy and Angela start to express their feelings, but disaster strikes when Angela discovers the missing ring, thrusting Tommy into a whirlwind of accusations. Determined to get to the bottom of the situation, he seeks out Edgar and Rick, only to find they have vanished. In a desperate bid, Tommy commandeers a delivery vehicle to track down his friends, discovering the ring's whereabouts. He confronts Christy and Frank, retrieves the stolen item, and returns it to Angela.
Unfortunately, the fallout from Tommy’s actions leads him back to jail, where Gray appears to bail him out, reigniting their partnership in crime. As the plot thickens, Ethan’s unexpected arrival at Viki’s home launches a sequence of events that exposes her manipulative schemes, with Tommy caught in the fallout. His conflicting loyalties are put to the test as he attempts to shield both Angela and Ethan from Viki's fabrications while learning of yet another of Viki's lies.
Tommy, witnessing the effects of Viki's duplicity on everyone around him, reaches out to Angela to join them for dinner at Viki's, unknowingly unraveling the very fabric of Viki's lies. As the evening unfolds, secrets come to light, revealing that Angela is not just Tommy's grief counselor but his parole officer. The fragile ties that bind Viki and Angela are severed, leaving Viki isolated and exposed against the backdrop of her deceit.
