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| No. | Episode | Airdate |
| 201 | CHUCK VERSUS THE FIRST DATE | 9/29/08 |
Chuck prevents Colt from obtaining the Cipher -- a device that would ultimately lead to a new Intersect. Chuck is told that this successful mission marks the end of his espionage career and the beginning of a normal life. Free from bullets and bombs, Chuck finally asks Sarah out on a real first date. But Chuck's role as the old Intersect is not good news for everyone as Casey deals with a difficult order assigned to him. Meanwhile at Buy More, Morgan devises an eccentric way to hire a new assistant manager. |
| 202 | CHUCK VS. THE SEDUCTION | 10/06/08 |
Chuck must go undercover to retrieve the Cipher from the Black Widow. But in order to get close to his target, Chuck must learn the art of seduction from the suave and sophisticated Roan. Unfortunately for Chuck, Sarah and Casey, Roan is no longer the world's greatest spy. Meanwhile, Morgan offers Captain Awesome some advice for a romantic night with Ellie, and Lester struggles to gain respect at Buy More as the new assistant manager. |
| 203 | CHUCK VERSUS THE BREAK UP | 10/13/08 |
Chuck is overcome with jealousy when his nemesis Bryce Larkin -- and Sarah's ex-lover and partner -- makes an unexpected return. Chuck and Sarah's growing feelings for each other are tested when their latest mission requires Sarah and Bryce to pose as an extremely affectionate couple. Meanwhile, Morgan faces his own challenge at Buy More when he must deal with a gang of bullies, from a neighboring sporting goods store in the strip mall called, the Mighty Jocks led by the fearful Mitt. |
| 204 | CHUCK VERSUS THE COUGARS | 10/20/08 |
Chuck learns more about Sarah's past when they run into her old high school nemesis Heather Chandler. Sarah's teenage insecurities come to surface and she tries to avoid Heather at all costs. Chuck, on the other hand, does everything he can to hear more about Sarah's hidden life. When Heather's nerdy husband Mark turns out to be a key player in a new mission, the agents must attend Sarah's high school reunion to prevent the sale of potentially dangerous super-bomber plans -- all the action ends with the ultimate cat fight. Meanwhile, Big Mike leaves town for a day and Buy More's new assistant manager Lester decides to implement a new sales policy. |
| 205 | CHUCK VERSUS TOM SAWYER | 10/27/08 |
Life in espionage takes its toll on Chuck and everyone is taking notice. Chuck tries to explain his unusual behavior to Ellie and to the quirky Buy More efficiency expert Emmett Milbarge, but a new assignment only complicates things. After a global terrorist comes searching for Jeff, Chuck is forced to socialize with Jeff in order to find out what role the oddball plays in the mission. Sarah, Casey and Chuck are all shocked when they discover that the fate of the world and the prevention of World War III rest in Jeff's hands. |
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