Pittsburgh, 1996. Jamie (played by Jake Gyllenhaal) finds himself working in an electronics store, engaging in flirtatious banter with various women to push sales on phones and stereos. His reckless escapades lead to a steamy encounter with Christy, the store owner’s girlfriend, which ultimately results in his dismissal when their private moments get broadcasted over the intercom.
Later that evening, Jamie joins his family for dinner. He learns that his brother Josh, a successful medical software entrepreneur, is willing to assist him in securing a position as a pharmaceutical sales representative. With Josh’s influence, Jamie lands a job at Pfizer after completing several seminar classes. Determined to make a name for himself, Jamie hits the pavement to peddle drugs like Zoloft and Zithromax, but finds the constant rejection from doctors disheartening. His partner Bruce (Oliver Platt), eager to elevate his own career by leveraging Jamie’s potential, encourages him to target Dr. Knight (Hank Azaria) to sway his colleagues towards prescribing Zoloft instead of Prozac.
Jamie devises a plan involving seduction and deceit, leading to him stealing Prozac samples and bribing Dr. Knight to shadow him in the office. Amidst this, he encounters Maggie (played by Anne Hathaway), a vibrant 26-year-old grappling with early-onset Parkinson's Disease. Their first meeting is jarring when she confronts him about his lies after he pretends to be an intern and violates her personal space.
As Jamie's personal and professional lives intertwine, he finds himself in a whirlwind fling with Maggie, characterized by passionate encounters and casual meet-ups. However, his actions soon attract the ire of Trey (Gabriel Macht), the aggressive rep for Prozac, who warns Jamie to stay away from Maggie due to the competitive nature of their work.
Their relationship becomes a mixture of tender moments and frustrating realities as Jamie navigates his growing feelings and the challenges posed by Maggie's illness. He finds success when offered the chance to sell Viagra, catapulting him into popularity amongst the medical community.
Through numerous ups and downs, Jamie and Maggie’s love story unfolds—not without conflict. Their discussions about commitment and intimacy reveal deeper fears, particularly following a visit to a Parkinson's convention that leaves Jamie shaken. As he dives into research for Maggie's condition, their relationship strains under the weight of expectations and the harsh realities of her disease.
Eventually, they separate, igniting Jamie’s reckless lifestyle filled with fleeting romances—yet leaving him emotionally hollow. A pivotal moment occurs when Jamie recognizes the depth of his feelings for Maggie, leading him on a frantic chase to express his love before their paths diverge completely.
In an emotional conclusion, Jamie confronts the complexities of love and choice, demonstrating the enduring bond they share despite life’s challenges. The film ends with a poignant montage, emphasizing the importance of cherishing each moment and pursuing one’s dreams amidst life's unpredictability.
