In the Buy More parking lot, Chuck's dismayed that his life still includes Buy More, guns and spies. He asks Casey why he's still the only intersect. Casey says the other cipher exploded and killed CIA Director Graham. Chuck's shocked about Graham, but still wants to know how that affects him. Casey tells Chuck he isn't leaving Buy More any time soon. Meanwhile, Lester continues his reign of terror as assistant manager, publicly calling out Jeff and Morgan for their transgressions. Chuck can't believe his life has come to this, but Morgan tells Chuck he has a great future and gets to go home to "that." "That" being Sarah, who walks up to Chuck and kisses him. Not out of affection, but as cover to whisper to him that he's needed for a national security emergency.
Chuck tries to persuade Sarah to go on vacation together over the emergency, but she tells him they can't date now that he's the intersect again. Chuck reminds her that she dated Bryce, but Sarah says Bryce was a spy; unlike Chuck, who's an asset she's been hired to protect. A passageway inside Orange Orange leads to a massive underground bunker the CIA built for operations. General Beckman tells Chuck and Sarah that Colt, a mercenary hired to steal the cipher, rigged a fake one with a Trojan horse that caused the deadly explosion. The real cipher may be in the hands of former KGB operative Sasha Banacheck, who's in town to sell it. Banacheck endured seven years of torture in a Bulgarian prison and didn't spill one secret. Beckman says only one agent was able to get close enough to put her in prison. That man is legendary lothario Agent Roan Montgomery, who also happened to flunk Casey twice in operative training.
Beckman assigns Chuck to find the off-the-grid Roan, but Chuck refuses. Sarah dangles the carrot that the sooner they get the cipher, the sooner Chuck can have the life he's always wanted. Chuck looks at the file and flashes on it. He sees Roan's address in Palm Springs, as well as Roan's swank James Bond lifestyle with women, tuxedos, martinis and best of all, Roan proudly displaying his assets in a Speedo.
In Palm Springs, Sarah tells Chuck that Roan is a department legend, a real James Bond type. Casey grouses that he's overrated, and admits that Montgomery failed him twice in his infiltration and inducement of enemy personnel class, a.k.a. seduction. Casey scoffs -as if he needed a class in that. At Roan's house, they find his door ajar, the house a mess and Roan under his bed - asleep, snoring and clutching a bottle of gin like a teddy bear. A sexy flight attendant surprises them on her way out of the house. When Chuck sees the reality of the legendary Roan, he fears he'll be the intersect forever.
At Chuck's sister Ellie's house, Chuck is mortified when Devon asks Ellie for a quickie in the shower. Ellie tells Devon that he hasn't taken her on a single romantic date since they've been engaged and wonders why they aren't more like Chuck and Sarah, who still have that romantic spark.
At another briefing, Beckman confirms that bad girl Banacheck has the cipher and their mission is to get it back. Beckman asks about Roan, and Casey and Sarah say they can't wake him. However, he's already up, fueling up on martinis and a shower to prepare for spy duty. Casey suggests torturing it out of her. Roan, decked in an Armani suit, struts into view, saying torture won't work on Sasha. He calls Beckman by her first name, Dianne, and clearly charmed by him, she doesn't object. Casey volunteers to seduce Sasha, but Roan says they need someone innocuous, someone she'd never expect to be an agent. Someone like Chuck.
At the Buy More, Devon can't find Chuck to help him on his romance tactics with Ellie so Morgan eagerly steps in to offer advice. He says he's studied Ellie for 19 years and knows what he's talking about. Devon tells him his plan: flowers, candles, wine and jumbo shrimp. Morgan says Ellie got sick from shrimp and shoots down Devon's idea to bring her pecan pie. He has a few ideas of his own for Devon.
Roan, with Sarah as stand-in, coaches Chuck on the art of seduction. Chuck wants to be himself, but Roan doubts a woman like Sasha would ever fall for a guy like Chuck. When Sarah defends Chuck, Roan wants him to prove he can be suave by kissing Sarah. Embarrassed, Chuck places a peck on her lips so awkwardly that Roan worries he's a virgin. When Roan says he'll get Casey to kiss Sarah, it's too much for Chuck and he kisses her passionately, flustering them both. Sarah leaves to "fix her lipstick." Casey, listening to them on headphones, overhears Roan telling Chuck he can teach him how to get Sarah, but first they need more gin. Casey says to himself, "We're dead."
Chuck, dressed to charm the stilettos off a former KGB operative, gets wired up with a mike in his ear so that Roan can coach him through the seduction offsite. Chuck learns that Sasha's known as the Black Widow, not because, as Chuck says, "She's African-American and her husband died," but because she kills her lovers .
Back at the Buy More, Big Mike tells Lester he's not an effective manager because his employees don't fear him. Lester eagerly asks how he can get them to fear him. Big Mike says make like a lion on Animal Planet: find the wounded gazelle and pounce.
At Sasha's hotel, Sarah and Roan are parked across the street, monitoring wireless cameras and microphones for Chuck's big mission to seduce the cold-blooded but sexy Sasha. Casey seethes as he bartends, watching Chuck stumble toward Sasha. His attempt to seduce her falls flat as she refuses his offer to buy her a drink - she's now a teetotaler. Roan hears that and worries that a geek like Chuck can't seduce her without alcohol. With Roan and Sarah feeding him lines in his earpiece, Chuck breaks through, asking Sasha if perhaps they met in St. Tropez. She smiles. He's found his in with the icy Sasha.
At Ellie's house, Devon starts his night of intense seduction, thanks to some "inside information" on Ellie's favorite things, courtesy of Morgan Grimes. But he's picked the wrong movie, the wrong dessert, and the wrong song to seduce his fiancÃ©e. Apparently Morgan, who has been smitten with Ellie his whole life, has purposely led Devon astray.
Back at the hotel, Sasha speaks French to Chuck and he wings it. But he gets distracted as he hears Roan and Sarah argue over Sarah's true feelings for Chuck. Sasha senses Chuck's hesitation, loses interest and walks off. Chuck asks Roan what is the "4th prong of the assault" for seducing Sasha. Roan says, "Be a bastard." Chuck channels Charles Carmichael and lays on the brutish charm. Sasha responds, telling him he can take her up to her room to make "mad passionate sex with me." Chuck is stunned as Sasha pulls him into the elevator and kisses him, which Sarah sees as the elevator doors close.
As Casey and Sarah rush to Sasha's room, Chuck is alone while Sasha changes in the bathroom. He asks where they are via his watch transmitter, then flashes on a knife sitting on a table, showing him all the lovers Sasha's killed. Panicked, he tells Casey and Sarah to get him out of there, and then asks Roan what to do. Roan asks if he ever told him about the night in Thailand with the king's daughter. He hasn't. Roan promises he'll get him out of there, and then tells him to go to the balcony, tie a bedsheet around his waist and go over the railing. Chuck says no way, as he's not a real spy.
Sasha exits the bathroom in a sexy leopard negligee, and Chuck flashes on her necklace, which is hiding the cipher. Sasha puts the moves on Chuck, concealing a knife she intends to stab him with. She whispers into Chuck's ear but is speaking to Roan! "Don't send a boy to do a man's job." She moves to stab Chuck but he locks her out of the balcony. Sasha is furious when she sees that "the boy" Chuck has stolen her necklace. He calls for Roan, who has fled the scene. Chuck climbs the balcony and escapes, skirting death when he falls safely on a plush outdoor loveseat. His elation is short lived. He calls Sarah to say he's escaped, but it's Sasha who answers, saying she's captured Casey and Sarah. She tells Chuck to bring the cipher to a rendezvous point or they die.
At the Buy More, Lester holds a late-night meeting where he presents "The Wheel of Misfortune," a game of chance he's designed to make his employees fear him. He wants his underlings to spin to "win" various work duties. There's only one way out of work, and that's landing on "You're fired." Morgan is first to spin the wheel and gets fired. In protest, Anna quits, then Jeff. Then everyone. Lester screams at the departing crew, "You're all fired! Do I have your attention now?"
Roan tells Chuck that Sasha's going to kill Casey and Sarah. When Roan won't help Chuck rescue them, Chuck asks him what happened to the world's greatest spy. Roan admits he's not the man he once was, but he's still alive - and not in love with one of the agents. Roan says lesson #1 in being a spy is "never fall in love." Chuck says he must not be much of a spy, and because Roan won't help him, adds that Roan isn't much of a legend. After Chuck unsuccessfully tries to contact Beckman to save Casey and Sarah, he sees Devon has been banished to the couch by Ellie. Devon wants make up for the Grimes-induced gaffe, saying he should have gone with his original plans of rose petals, pecan pie, dinner and champagne. But, with his schedule as a doctor, he worries he doesn't have time to pull it off.
At the Buy More, Lester tells Chuck that he fired most of the staff and is in a panic to get them back. Big Mike approaches; his only concern is that Lester got the managers-only doughnuts. Later, Lester holds a second meeting and says everyone gets a practice spin on the Wheel of Misfortune. Led by Anna, they refuse to spin and demand that he make changes to get them back, which includes taking a spin on his own wheel. Lester spins and gets diaper station duty, much to the amusement of the crew. Roan enters the store and asks Chuck what he meant when he said he wasn't a legend. When Chuck says he meant it, Roan asks him his rescue plan, clearly back in to help Chuck get Casey and Sarah back.
At the rendezvous point, a messenger brings a package to Sasha. Inside is a phone, which rings. On the line is Chuck, telling her to meet him at Buy More. In the store, Chuck addresses Sasha over the PA system and through video, broadcast over the store TV displays. One of her men catches up to him and traps him on the roof. Sasha says with Chuck trapped, she doesn't need hostages. She turns to shoot Casey and Sarah, but Roan sneaks up behind her and tells her to drop it. Sasha is chagrined that her old nemesis has tricked her.
When Casey and Sarah use the distraction to disarm Sasha's goons, Sasha applies a spinning back kick and disarms Roan. She takes Sarah by gunpoint and threatens to shoot her if Chuck doesn't give her the cipher. Roan coaches him through the earpiece, telling him to remember his Thailand story. The Thailand escape involves swinging from the rafters on a bedsheet. Chuck wraps the giant "Under New Assistant Management" banner around his waist and swings straight into Sasha, knocking her unconscious. Roan, impressed with his protÃ©gÃ©, says, "Now that's what I call a spy."
In the morning at the Buy More parking lot Big Mike sees that the banner, haphazardly repaired with duct tape, now reads, "New Ass Man." Big Mike is confused, saying, "I ain't new."
On the way to their house, Devon apologizes for not having more moves. Ellie says it's important that he tried. They open the door, and to both of their surprise, the place is covered in roses with a candlelit dinner on the table. Ellie thinks Devon did it and praises him on how good he was at setting up the surprise. Though he has no idea how the place got that way, he happily takes the credit.
Roan says his goodbyes. He pulls Chuck aside and coaches him on a follow up, known as "The Montgomery." He says to surprise Sarah at home wearing a dinner jacket, bearing red wine and single red rose. After imparting that last bit of advice, Roan gets a call from "Diane," (General Beckman) and assures her he's on his way. Chuck goes to Sarah's apartment with wine and rose, eager to employ "The Montgomery." When she opens the door, she's surprised. But Chuck has an even bigger surprise coming to him when Bryce walks up behind Sarah and says, "Hello Chuck, miss me?"