We start out on a yellow Cabriolet with the strains of Chumbawamba as title cards tells us it's San Diego in 1998. The driver of said Cabriolet is a frizzy-haired, brace-faced, teenage Sarah (awww), who arrives home to discover ATF agents at her house. She gets teary, but only for a minute (this is Sarah, after all), before she runs to a tree across the street, digs up a box full of money with a note that says, "In case of emergency. Love you, Daddy." We pass to the present by way of Sarah's much more beautiful face. She and Chuck are in the Buy More making plans for their fake date. She spots Nicole Richie, who gives her a bitchy look (does Nicole Richie give any other kind?) and stalks her, as Sarah tries to flee. It's very suspicious. Chuck's being cute about their date the whole time Sarah's trying to get away, telling her she doesn't need to be so dodgy about pad Thai noodles. Sarah heads straight to Casey and gives him some secret message. He does something with the inventory gun that is clearly much more than that, and tells Sarah to take Chuck to the Orange Orange's Super Secret Lair (OOSSL).
Sarah leaves Chuck in a cool room filled with a gigantic computer that he is possibly more in love with than he is with Sarah. He knows everything about the computer, and speaks geek to himself about it, which is probably just gibberish, but I am not geeky enough to know that. (I swear! I'm not!) Then he does exactly what Sarah asked him not to: touches the computer. He pulls up a bunch of surveillance cameras (Buy More; courtyard; "awkward," which is Ellie and Awesome sitting up in bed in the middle of the day -- WHO does that?!), finally landing on Sarah talking to Nicole Richie at the Orange Orange. Nicole swears she knows Sarah, but Sarah's trying to pretend she has a familiar face, or has done some commercial acting. Nicole finally realizes they went to high school together, and Sarah's name is Jenny Burton! Chuck is like, "Jenny Burton?" as if that's just as boring a name as Sarah Walker, and he wanted it to be something exotic, like, oh, I don't know Yvonne Strahovski. Nicole introduces herself as Heather Chandler, but then corrects herself, saying she's Heather Ratner now because she married Mark Ratner. Flashbacks show us that Heather was a bitchy cheerleader and Mark Ratner (Ben Savage) was a huge nerd who got shoved into his locker by jocks, while Heather stood there laughing. Not cool, Heather. Then again, she's a Heather. Heather explains our episode title by saying "James Buchanan High. Go Cougars!" And here I thought it would be an episode about Chuck versus a group of older, hot women. But I guess we had Chuck with that type of cougar a couple weeks ago.