Stacy Holt, a detail-oriented associate producer on The Kippie Kann Show, firmly believes that fortune favors the prepared. Her boyfriend Derek, though seemingly the embodiment of this principle, harbors secrets about his past romances that only add to her concerns. While reviewing show tapes at home, Stacy stumbles upon a familiar face—Lulu, Derek's ex-girlfriend and a French model.
Derek's reluctance to discuss his past only intensifies Stacy's anxieties, prompting her to share her worries with her coworkers, Barb and Ira. Inspired by Ira's clever idea of using PalmPilots as a digital "little black book," they devise a plan to delve into Derek's digital life. Under the pretense of potentially inviting Lulu back onto the show, they question her about her relationship with Derek and unearth the truth—Derek was taken from his committed girlfriend Joyce by Lulu's allure.
As Stacy digs deeper into Derek's history, her insecurities grow stronger. She becomes fixated on his answering machine messages and goes through his memorabilia. Discovering that there are women from his past, including Joyce and Rachel, just a click away in his PalmPilot, she decides to meet Rachel under the guise of research, only to realize that Rachel is actually a gynecologist.
This revelation sets off a chain of events where Stacy interrogates Rachel regarding her ties to Derek, unveiling that they share custody of his cherished dog, Bob, and still see each other on occasion. Feeling like an outsider, Stacy witnesses their cordial relationship, which deepens her sense of unease.
Simultaneously, she develops a friendship with Joyce, initially under false pretenses. As their bond grows, so does Stacy's guilt, aware that her probing has contributed to the ending of Derek and Joyce's relationship. The revelation hits hard: it was Lulu who caused Derek to confront his authentic feelings for Joyce.
Now, as Stacy contemplates the repercussions of her actions, she questions whether her pursuit of truth has ultimately damaged her relationship with Derek beyond repair.
As The Kippie Kann Show approaches its live broadcast, Stacy assumes a critical production role, preparing to weave a significant storyline into the episode. Her investigative discoveries will become the centerpiece of the narrative, thrusting her into the spotlight. However, the harsh reality surfaces before the audience; a script crafted by Barb ensnares Lulu, Rachel, Joyce, and Derek, leading to emotional upheaval. The fallout hits hard for Joyce and Derek, leaving their relationship in disarray.
In a moment of sincere reflection, Stacy offers her apologies to the cast and tenderly concludes her relationship with Derek, recognizing its inherent flaws. With her conscience clear, she encourages Derek to mend things with Joyce before she departs amid an audience’s applause.
In the aftermath of this chaotic episode, Stacy embarks on a journey of self-reflection during a heartfelt interview with Diane Sawyer. This introspective dialogue sparks her personal growth and ultimately opens doors for her career, as she secures a position under the tutelage of the esteemed journalist. Excited about her new path, Stacy is elated to encounter her idol, the iconic Carly Simon, and revels in the magic of this unexpected meeting.
