Chuck Bartowski is an average computer geek until files of government secrets are downloaded into his brain. He is soon scouted by the CIA and NSA to act in place of their computer.

As Chuck is beginning to adapt to his new life as a spy, a doctor who could possibly "cure" Chuck is murdered. Chuck then begins a high-speed fight for his life, all while trying to decide which of his two new colleagues might be out to get him. Meanwhile, Chuck's sister Ellie invites Sarah to dinner to meet the family.

Chuck needs the help of Morgan and the Nerd Herd to prove that he is ready to become the store's assistant manager. Sarah and John assign Chuck his first undercover spy mission to foil a terrorism plot.

Chuck's latest mission has him raiding a Malibu mansion to grab a million dollar diamond being used to fund terrorism. Tagging along is an attractive but less-than-trustworthy DEA agent.

Returning to Stanford, the University that expelled him, Chuck has to help a former professor who is a government agent being hunted for a sensitive top-secret file he has in his possession. At the same time, Chuck learns much about himself and about the death of his friend Bryce Larkin.

While coping with the realization that Sarah still has feelings for Bryce, Chuck must assume his toughest cover yet by going on a mission as Sarah's husband. The team must foil the plot of a politically connected counterfeiter, who may be endangering the lives of Anna, Morgan and Anna's parents. Both Morgan and Anna also find themselves in the cross hairs.

Two new characters are introduced, both of whom want to take the Intersect. One is a beautiful, young female enemy agent that works in the Pita Palace next to the Buy More, and the other is a handsome CIA agent who is posing as an undercover police detective investigating a theft at the Buy More who wants to take Chuck into his custody. The former quickly blows Chuck's cover, while the latter kidnaps him and makes him vanish from his former life.

"Chuck Versus the First Date" is the second season premiere of the action-comedy series Chuck. It first aired on September 29, 2008. Chuck's time as the Intersect is coming to a close as the CIA and NSA have completed construction of the new Intersect.

Chuck goes undercover at Sarah's 10-year High School reunion, where they meet the girl that tortured Sarah back in the old days.

Sarah is forced to confront a secret from her past and feels she must do so alone, while Chuck urges her to let him help. When Sarah encounters her original handler, Kieran Ryker, she fears that he will harm those closest to her, including her mom.