The story follows Jay Wheeler, portrayed by Scott Speedman, the adventurous yet troubled "black sheep" of a wealthy family. Living life impulsively, Jay spends his days engaging in fleeting relationships with various women but never truly connects with any of them. His extravagant lifestyle leads him into deep financial trouble, owing Mr. Vincent, a menacing loan shark, a staggering $37,000 after losing everything he had on horse racing. Despite his struggles, he is unable to turn to his affluent family for help and finds himself constantly at odds with the law, currently on probation.
While serving community service as a janitor in a local hospital, Jay crosses paths with Daisy Kensington, a young woman portrayed by Evan Rachel Wood, who has grown up in isolation and is now a psychiatric patient. Under the supervision of Dr. Bertleman, played by J.K. Simmons, Daisy is sheltered and vulnerable, and it’s here that Jay takes immediate action to protect her from an inappropriate incident involving hospital staff. This act of bravery marks the beginning of a turbulent yet transformative journey for both of them.
When Jay decides to leave the hospital, Daisy, with nowhere else to go, follows him. Jay contacts his family, who invite him to his brother's wedding, leading him to concoct a lie about having a girlfriend who is a nurse. Desperate to maintain this facade, he enlists the help of his friends, all of whom refuse, leaving him no choice but to bring Daisy along.
At the wedding, Daisy charms Jay's family with her quirky and genuine personality, but amidst the festivities, she reveals her tragic past of having killed her mother in a fit of rage, which landed her in the psychiatric hospital. Jay's father, Mr. Wheeler, represented by Treat Williams, grows suspicious of Jay’s intentions, prompting Daisy to suffer a panic attack. Following the chaos, Jay confides in his parents about his true situation, admitting that both he and Daisy are in precarious circumstances.
As they escape in a classic RV, they are pursued by the law, yet they manage to bond over their shared experiences. An incident on the road brings them even closer when Daisy cleverly distracts a police officer while Jay hides, allowing them to evade capture temporarily. However, tensions escalate when Daisy, terrified of being returned to the psychiatric hospital, crashes the RV in her attempt to flee.
In a dramatic turn of events, Jay confronts his own struggles against the backdrop of Daisy’s trauma. He explains that the voices which haunted Daisy’s mother were not her own, shedding light on the nature of her suffering. Despite their precarious situation, they find hope in each other's company.
As the narrative progresses, Jay’s dire situation reaches a climax when he is arrested after an altercation at the hospital. Following this, his mother, played by Kate Burton, intervenes to help bail him out. The film concludes as Jay receives a letter containing a $40,000 check from his father, which allows him to settle his debts. In a heartfelt moment, he reunites with Daisy at the hospital entrance, and the two leave together, ready to face the uncertain future hand in hand.
