Chuck and Casey are in the Buy More parking; Chuck still wondering why he's still the only Intersect, Casey tells him that the other cipher exploded and killed CIA Director Graham. Casey tells him that he isn't leaving the Buy More anytime soon. Chuck has a conversation with Morgan and believe he's life isn't going anywhere, when Sarah walks in the Store and Kisses him as part of the Cover. Sarah leads Chuck down a massive underground bunker the CIA built for operations at the Orange Orange. The General tells Chuck and Sarah that the real Cipher could be still out there in the hands of Sasha Banacheck. Beckman says only one agent has ever got close to her, Roan Montgomery. Beckman assigns Chuck and Sarah to find Roan and help them get the Cipher.
Chuck refuses at first but after a little conversation from Sarah he changes his mind. Chuck, Casey and Sarah find themselves in Palm Springs at Roan's place where he's passed out underneath his bed with a bottle of Gin. Back at Ellie's apartment she asks Devon why he still hasn't taken her out on date since they've been engaged and wonders why they aren't more like Chuck and Sarah. Beckman confirms that Banacheck has the cipher and their mission is to get it back. Casey suggests torturing her when Roan comes in the scene and tells that won't work. Roan suggests seducing her, Casey volunteers but Roan wants' someone she'd never expect to be an agent, Someone like Chuck.
At the Buy More Devon gets advice from Morgan about setting up a romantic night with Ellie. 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. Roan wants Chuck to kiss Sarah. Embarrassed, Chuck places a peck on her lips. When Roan suggests getting Casey to kiss her it's too much for Chuck and he kisses her passionately. Chuck is being wired up before going to seduce Sasha; he learns that she kills her lovers. Back at the Buy More Big Mike tells Lester to toughen up as Assistant Manager and make the employees fear you. At Sasha's hotel, Sarah and Roan are parked across the street, monitoring wireless cameras and microphones for Chuck's big mission to Sasha.
Roan and Sarah feed him lines his earpiece after she first refuses a drink. Chuck moves on to a different subject asking Sasha if perhaps they met in St. Tropez. At Ellie's House, Devon starts his own seduction which doesn't go according to plan as Ellie finds out that all of the favourites that Devon was suggesting are all favourites of Morgan. 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 losses interest and walks off, Roan tells him to be like Carmichael and soon lays of his charms. Sasha responds, telling him he can take her up to her room to make love to her. Chuck gets in the elevator with her as Sasha plants a kiss on 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. Chuck flashes on a knife showing him all the lovers Sasha's killed. Chuck wants to get out of their quickie Roan suggest he use a bed sheet around his waist and go over the railing. Sasha then comes out and Chuck flashes on her necklace, which is hiding the cipher. Chuck manages to grab the necklace and then dangles of the balcony just as she was about to use a knife on him. When reaching the bottom Chuck calls Sarah to tell her that he's got the Cipher, but it's Sasha who's answered the call 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 meeting with the employees where he presents "The Wheel of Misfortune," a game of chance he's designed to make his employees fear him. Morgan spins it first and it lands on "You're Fired" in protest the rest of staff quit.
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. At the Buy More Lester tells Chuck that he fired most of the staff and is in a panic to get them back. Lester get's the employees back and compromises with them by spinning the wheel himself. Roan enters the store and agrees to help Chuck get Sarah and Casey back. Chuck re-arranges the plan by making Sasha and her goons rendezvous at the Buy More. 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. A fight soon breaks out, with Sasha capturing Sarah and threatening to shoot her unless Chuck gives her the Cipher.
Roan coaches him through the earpiece, telling him to remember his Thailand story Chuck wraps a giant banner his waist and swings straight into Sasha, knocking her unconscious. Devon and Ellie open the door, and to both of their surprise, the place is covered in roses with a candlelit dinner on the table. Roan says his goodbyes and tells Chuck if he wants to surprise Sarah at home go wearing a dinner jacket, bearing red wine and single red rose. Chuck reaches Sarah's apartment he gets one hell of a surprise in Bryce Larkin.