Jamie Randall, Jake Gyllenhaal is a charming, quick-witted electronics-store clerk in Pittsburgh during 1996 who treats flirting as a sport. He talks customers into buying phones and stereos while playfully chasing the store owner’s girlfriend, Christy, Nikki DeLoach. Their flirtation takes a sharp turn when Christy’s boyfriend is alerted by an intercom, and Jamie is abruptly fired. That night, over dinner at his parents’ house, he learns that his father and sister are doctors and that his brother Josh, Josh Gad, has made a fortune in medical software. Josh offers to help Jamie break into the pharmaceutical world, believing the sales game could be his ticket to a bigger stage in Chicago.
With Josh’s backing, Jamie dives into Pfizer’s trainee program after a crash course in seminars and sales pitches. He practices in parking lots and hospital corridors, trying to persuade doctors to prescribe Zoloft and Zithromax, only to be met with repeated refusals. His partner in the field, Bruce, Oliver Platt, sees a fast-rising opportunity in Jamie’s ambition, hoping the younger man will pave the way for Bruce’s own ascent toward the Chicago market and a steadier life with his family. Bruce pushes Jamie to win over Dr. Stan Knight, Hank Azaria, hoping that once Knight approves Zoloft, the rest will follow.
Jamie’s shadowing of Dr. Knight begins a rapid ascent into pharmaceutical theater. Dressed in a white coat, Jamie fakes intern status and watches Knight treat Maggie Murdock, Anne Hathaway, a 26-year-old waitress diagnosed with an early onset of Parkinson’s disease. Maggie notices a suspicious lump during the examination, which turns out to be a spider bite, and punches Jamie in the parking lot for misrepresenting himself and peeking at her. This encounter seeds a volatile but magnetic dynamic between them, as Jamie pursues Maggie with relentless charm, while Maggie keeps him at arm’s length in the early days.
Jamie’s professional world grows more complicated as he flirts with his receptionists and, unscrupulously, steals Prozac samples from Knight’s cabinet to fuel his social swagger. He also bribes Knight with cash to look the other way so he can shadow the doctor longer. Knight’s patient circles widen Jamie’s access, and soon Jamie’s career begins to surge as he pivots toward Viagra, riding a wave of new popularity as doctors start prescribing the broader portfolio his company is marketing.
Amid the professional climb, Jamie and Maggie’s personal chemistry intensifies. Maggie, who lacks health insurance and faces the practical burdens of her disease, is drawn to Jamie’s vitality and determination, even as she warns him about the fragility of their situation. Their relationship becomes a rollercoaster of passion and practical reality: Maggie’s illness shapes their choices, and Jamie’s ambitions pull him toward bigger opportunities and bigger risks. He pays for Maggie’s visits to specialists and covers travel costs to conferences and seminars in an effort to find delays in the disease’s progression or credible therapies, sometimes maxing out his credit cards in the process.
The film threads a tension between Tamagotchi-like romance and corporate machinery. Jamie’s drive to close deals collides with the consequences of his deception, and Maggie’s fears about her illness complicate his ambitions. They argue when she worries about finances and treatment access, and Jamie’s response oscillates between stubborn devotion and pragmatism. A pivotal moment arrives after a conference in Chicago, when Maggie is invited to a Parkinson’s convention across the street for people living with the disease. The event exposes Jamie to a broader sense of purpose and the human stakes behind the medical industry, particularly as he witnesses the real kinds of struggles faced by patients and their families.
A montage follows: Jamie immerses himself in online research and medical libraries, seeking every possible angle to help Maggie, while pushing Knight for more information about specialists. He begins to realize that love cannot erase a diagnosis, and Maggie’s outlook evolves as she learns to navigate her life with Parkinson’s. The couple fights over the feasibility of their relationship, and Maggie ultimately pushes him away, a breakup that leaves Jamie desolate yet more determined to change his trajectory.
In a late-night pajama party at a colleague’s home, Jamie reconnects with his own reckless side, impulsively taking Viagra and joining a threesome with two coworkers. The experience hurts him physically and emotionally, especially as he confronts the consequences of his choices and the hollow thrill of casual sex. Meanwhile, Josh reassesses his own life after watching his brother’s trajectory and decides to return to his wife, recognizing what truly matters.
A highlight awaits at another dinner where Jamie learns that his promotion claim was a misfire and that he has instead received a raise that won’t fix the deeper issues in his life. He returns home to discover a video he and Maggie made, sparking the realization that he wants to be with her and that his future may lie not in Chicago’s fast lane but in a shared life with Maggie. He races to catch up with her as she makes a med run to Canada, and the pursuit culminates on a highway rest stop where Maggie offers him a final chance to speak from the heart.
In a heartfelt confession, Jamie tells Maggie that she makes him a better person, that he loves her, and that he would choose their reality with all its problems over any easier path. Maggie, moved by his sincerity, acknowledges that she will need him even more, but she resists asking him to bear an impossible burden. Commissioner of emotion drives the moment, and Jamie’s rebuttal lands with quiet force:
> "you didn't"
The film closes with a hopeful montage: Jamie and Maggie living together as he studies for medical school, while he reflects on the idea that money is not the sole measure of a life well lived. A final voiceover by Jamie contemplates seizing every day, embracing passions, and choosing dreams over easy success, leaving viewers with a quiet reminder to pursue what truly matters.
Overall, the story follows a flawed, ambitious salesman who learns that love and illness force him to reframe success, showing growth from reckless scheming to a more compassionate, committed pursuit of a shared future.
