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Chuck Versus the Seduction
Season 02, Episode 02
Air Date October 6, 2008
Writer Matt Miller
Director Allan Kroeker
Previous Chuck Versus the First Date
Next Chuck Versus the Break-Up
"I promise you, Chuck Bartowski on his own can seduce this woman."

Chuck Versus the Seduction is the second episode in season two, which aired on October 6, 2008. It is the fifteenth episode overall.


A legendary seduction instructor teaches Chuck how to spring a trap for a sexy spy.

Full Story[]

Arriving at the Buy More, Chuck tells Casey how disappointing it is that he was supposed to be free from the Intersect and the government. Casey tells him until they can rebuild the Intersect again, he's not leaving the Buy More anytime soon. Chuck asks if the Intersect has a computer problem that he can help with but Casey answers it was blown into a million pieces, along with Director Graham, shocking Chuck. Meanwhile, Lester is on a power trip as the new Assistant Manager. He makes it clear that he is going to be running the Buy More with an iron fist.

Sarah shows up in the Buy More and tells Chuck that there's a national emergency. They head to Orange Orange – the CIA has created an underground bunker accessed through the shop. Surprised, Chuck asks if the government is planning a permanent residence in Burbank. General Beckman, appearing on a screen, states that it all depends on him. Moving on to the briefing, she states that the real Cipher is still out there. They think it might be in the possession of Sasha Banacheck, a former KGB agent, and she might be in town to sell it. Casey suggests torture to get it out of her, only for Beckman to respond that Sasha spent seven years in a Bulgarian prison, and she didn't crack. They are going to need the help of another agent, who knows everything about Sasha and put her away – Roan Montgomery.

Roan apparently flunked Casey twice in training. He's off the grid now, so they need to use the Intersect to find him. Chuck walks out – he wants nothing to do with the spy life anymore, with all the dangling off buildings, guns pointed at his head, and his life put in danger. Sarah chases after him, telling him that the faster they get the Intersect out of the way, the faster he can lead whatever life he wants, with whoever he wants – Chuck, of course, does as Sarah asks.


Training with Roan

Chuck flashes on Roan's picture – he lives in Palm Springs. And he's a player, a ladies' man, a real James Bond type. He's a legend, apparently, though Casey thinks he's overrated. Sarah asks him what class he was in; Casey answers Infiltration and Inducement of Enemy Personnel aka "Seduction School". They show up at his house and find him passed out under his bed – an attractive stewardess is also there, one of Roan's conquests.

Meanwhile, Captain Awesome and Ellie keep having some problems. Awesome hasn't taken Ellie out on a real date for a long time. Ellie is envious of Chuck and Sarah.

Sarah and Casey tell Beckman about Montgomery's situation – he's a drunk. Finally, Montgomery shows up, dapper as ever. He gives a sly greeting to Beckman, to which she reciprocates. He then says that Sasha has to be seduced. Casey volunteers but Roan, calling him Agent Frankenstein, says that they need someone not CIA, someone no one would expect – someone like Chuck.

Meanwhile, Lester gives Chuck some grunt work, but he leaves instead and is told his mission – he has to seduce Sasha. To do that, Roan gives him a crash course in seduction. Roan keeps giving advice – he tells Chuck to try out his seduction methods on Sarah, he must kiss her. When he finally does, it turns out quite passionate. Roan is impressed – he gathers that it was not the first kiss those two shared.

Awesome shows up at the Buy More, gets tips for a romantic evening with Ellie from Morgan. Morgan knows a whole lot more about Ellie than Awesome does, it turns out. Devon is a little bit taken aback. Devon bases his date on Morgan's advice. Unfortunately, all the night's events revolve around Ellie's eighth grade persona. Ellie is not happy. Lester gets advice from Big Mike on how to strike fear into the employees – find the wounded gazelle and pounce.

Pre-mission, Chuck is dressed very well, and Sarah gives him a pep talk. Roan drops a bomb – Sasha is known as the Black Widow because she kills all her mates and Chuck needs a gun. Chuck has Roan in his ear as he enters the bar. Casey is the bartender. Chuck orders two martinis after sitting down with Sasha, who says she doesn't drink any more. She goes to the bar, Chuck follows, with Roan's advice to mention St. Tropez and the piano players at the Intercontinental Hotel.

Roan spills gin on their surveillance equipment, and they lose contact with Chuck. He is then unable to respond to Sasha, who whispers something to him in French. Sasha, disappointed, leaves. Meanwhile, Chuck overhears Sarah defensively tell Roan that she has no feelings for Chuck, that he is only her asset and that is it. Chuck is hurt by this. Sarah jumps out of the van, and heads inside.

Chuck decides that this isn't over. He asks Roan for the fourth prong in his seduction technique – Roan tells him to “be a bastard.” Chuck pursues Sasha. He is harsh and forceful – she will be missing out on the greatest night of love-making she will ever encounter if she goes upstairs alone. And it works. Sasha invites him upstairs for some “passionate love-making.” Sarah and Casey watch as the elevator door closes.


Chuck works on Sasha

Chuck enters Sasha's suite, and while she is in the other room, he flashes on a knife, and he immediately wants to leave. But, after Sasha comes out of her bedroom, wearing some lingerie, Chuck flashes on her necklace – it's The Cipher. Sarah and Casey approach the room, see the two bodyguards outside the hotel room. Sasha knows what's up – she says hello to Roan via Chuck's earpiece.

Chuck retreats to the balcony, and closes the door, after he manages to steal the Cipher from her neck. He tries to climb up to another balcony but is kicked off. He plummets down, but lands on a well-placed overstuffed chair by the pool. Chuck tries to speak with Sarah, but Sasha and her men have Sarah and Casey. Sasha tells Chuck that if he ever wants to see his partners again, he has to meet her alone the following night.

In the Buy More, Lester has a late meeting with his employees. He unveils the Wheel of Misfortune. He chooses Morgan to christen the wheel. He spins and lands on the thin strip that says, “You're Fired.” Morgan leaves, and there's a revolt. Everyone walks out.

Roan meets Chuck at his apartment, and tells Chuck that if he shows up tomorrow, there will be three dead agents instead of just two. Chuck tries to convince Roan to help, but Roan refuses, saying he's not the one who is in love with his partner. Roan then assures Chuck that Sarah has feelings for him and asks if she's worth dying for. Chuck says yes. Roan tells him that rule one is never fall in love. Chuck responds that he isn't much of a spy, but then Roan isn't much of a legend.

Chuck tries to contact General Beckman, he can't get a hold of her. He then heads to the Buy More and finds that no one is there; It's only Chuck and Lester. Lester begs Chuck to help him, that he's fired the rest of the staff. Chuck leaves him to sort it out, and Lester brings the employees back. He says that Morgan can get another spin. They say no one spins. They negotiate terms for them to come back; the last one is for Lester to spin the wheel. He does and ends up getting diaper station duty.

Roan shows up at the Buy More, he's ready to help. He wants to know what the plan is. Chuck tells him he wants to just show up with the Cipher. Roan says they need a better plan.

At the shipyard, a package shows up for Sasha. It's a cell phone. When it arrives, it rings, and Chuck tells her a location for the meet – it's the Buy More. Sasha with Sarah, Casey and her crew show up. Chuck addresses them over the monitors. One of the bodyguards finds Chuck, though, and chases him to the roof.


Pulling "The Montgomery"

With Chuck trapped, Sasha figures it's time to kill the hostages. As she's about to shoot, Roan puts a gun to her head, tells the henchmen to drop their weapons. Sasha does, but a fight breaks out. Sasha ends up getting a handcuffed Sarah in a choke hold at gunpoint. She drags a choking Sarah out to her car, followed by Roan and Casey and says that she will kill Sarah if the Cipher is not brought to her. Chuck, on the roof, unhooks a banner and readies to make a leap. He ties it around his waist and jumps. slamming into Sasha and freeing Sarah.

Team Bartowski is debriefed, they will try to get the intersect repaired, at which point Chuck's “nightmare” will be over.

Roan says goodbye to Chuck and gives him some romantic advice – show up at Sarah's in a white dinner jacket with a single red rose. Chuck takes his advice and arrives to find Bryce Larkin in Sarah's room.


  • This is the first episode to mention 'Ass Man' which becomes the nickname for the Buy More Assistant Manager.
  • The only other appearance of Roan Montgomery is Chuck Versus the Seduction Impossible.

Guest Stars[]


Chuck: [Sarah kisses Chuck] Is that, uh, a real kiss or a cover kiss? Because I'm confused right now.
Sarah: It's a "we-have-a-national-security-emergency and-I-need-to-speak-to-you-privately" kiss.
Chuck: See? I knew I felt something. [Sarah pulls him away] Who's your mama!?


Chuck: All right. Guys, sounds like a blast. Really, but you can count me out on this one. No more dangling me off of buildings, no more guns being pointed at my head, no more putting my life in danger. I am going back to my peaceful, quiet, albeit degrading, life at the Buy More, so have fun on the mission, and really love what you've done with the place.


Casey: Let's go Lover Boy, I need your services in a romantic capacity.
Chuck: Oh! I'm flattered. I just hope Sarah's involved.


  • "Desert Eagle" by Ratatat (Chuck and Casey discuss the bombing of the new Intersect)
  • "At The Checkout Counter" by Billy Martin
  • "Do You Believe In Love" by Huey Lewis And The News (Sarah arrives at the Buy More)
  • "Just Browsing" by Billy Martin
  • "65 Bars and A Taste Of Soul" by Charles Wright and The Watts 103rd Street Rhythm Band
  • "Right Here Waiting" by Richard Marx (Devon seduces Ellie)
  • "Do You Believe In Love" by Huey Lewis And The News (Ellie and Devon arrive at home)
  • "Love It All" by The Kooks (Chuck visits Sarah and finds Bryce)
  • "Di' tu se fedele" from the opera Un Ballo in Maschera by Giuseppe Verdi (Chuck seduces Banacek)