Starts out in Tehran, Iran looking at a Monet-like water lilies painting that is in a run down room with other paintings. Two men are looking at the painting and then one of them shoots the other one and takes the painting.
Next scene opens on a fragile crate in the Madrid, Barajas airport two weeks after the the first scene. A man with a pony tail opens the crate to reveal the same water lilies painting. The pony tailed man then shoots the man who had stolen the painting from Iran and takes the painting.
The next scene opens with a cloth covering being removed from the water lilies painting. A British man thanks the man with the pony tail and gives him a briefcase full of money. Then the British man shoots him.
One month later in northeast Los Angeles...
A gun is being pointed at Chuck's head and he is begging the person not to shoot. A kid, at the Buy More, complains that thats is the problem, that is can't shoot. Chuck offers to fix it without any hesitation and fixes it with a balled point pin. The kid starts playing the video game again. Harry Tang walks up behind them and tells Chuck that Big Mike wants to see him but Chuck tells him that he is with a customer. Tang leaves but then Big Mike comes up behind him and demands Chuck to come immediately. Chuck whispers to the kid to pause the game.
In Big Mike's office Big Mike grills Chuck on what he wants out of like and where he sees himself in the next five to ten years. A question Chuck is not able to answer. Big Mike indicated that if Chuck wants the Assistant Manager's position that he needs to prove that he both wants it and can handle it.
Chuck leads the other Nerd Herders into the back room and explains that they have two days to fix a bunch of old computer equipment or Big Mike will give the Assistant Manager's position to Tang. Morgan then bursts in to inform Chuck that Sarah is there to see him.
Chuck walks up to Sarah in the front part of the Buy More and asks him to kiss her. He awkwardly tries to do so for their "cover" and then she leads him to the home theater room. Casey sees them go in there and beelines for the theater room. Morgan tries to stop him but Casey knocks him over. Sarah brings out pictures of all the men that were shot at the beginning of the episode. Sarah and Casey hope he will flash on them but then Jeff walks in on everything wanting to nap in there. Chuck flashing on the picture of the water lilies painting that is on the front of the newspaper Jeff is carrying. He sees "La Ciudad", "Art Auction tomorrow night", CIA documents, weapons, and the water lilies painting from before. And Chuck concludes that La Ciudad will be at the Art auction tomorrow night.
At Chuck's home Ellie congratulates him for the Assistant Manager's job that he doesn't have yet. He talks about the not so outstanding perks associated with the potential raise. Then Ellie and Morgan start to discuss Chuck and his past, present, and future as if he wasn't standing right next to him. So Chuck reads a magazine.
Flash to Sarah's apartment, located in Chuck's building, where Sarah and Casey are getting debriefed about La Ciudad. La Ciudad was last tracked by MI6 in London but they lost him. Sarah hopes to catch him at the art show but since no one has ever seen La Ciudad and lived they do not have any idea what he looks like. Casey decides that they should take Chuck with them because everything known about La Ciudad was put into the computer that is now in his brain. Flash back to Chuck's apartment where Morgan and Ellie are still talking about Chuck's life and if he is ready for the real world or not when Captain Awesome joins in on planning things out for Chuck. When they finally ask him what he wants to do he goes to bed with a simple "Good Night Team Bartowski."
When Chuck enters his room he is surprised with Casey staring at him through his open window informing him that he has been assigned his first mission and "Hope you're ready for the real world."
At the Buy More, Chuck is grilling Casey on what he should wear on the mission. When Chuck asks what kinds of moves he might need in a fight Casey asks him if he knows how to Tango, leaving Chuck quite confused. He then walks off to go work on the old computer equipment that Big Mike had wanted the Nerd Herders to fix when Morgan shows him that Sarah has just come in and is ready to leave for their "date." Lester and Ann tell Chuck that everything is almost done and that he is free to go. Sarah and Chuck go over his cover for the evening which ends up being a version of himself that he had though would have come true post Stanford graduation. They banter a little about Bryce's betrayal as well.
Back at his apartment Chuck asks Ellie if she knows how to tango and explains he that he thinks he might need it that night. Then Captain Awesome comes out of a room in his boxers and offers to teach him how to tango. As Chuck and Awesome tango a montage of Sarah, Casey, and Chuck getting dressed for the evening out.
In the limo preparing to enter the art auction Sarah gives Chuck a watch with a tracking device. Chuck reveals he learned how to tango and Sarah and Casey start to laugh as Chuck realizes that it was just a bit of spy humor at his expense.
Back at the Buy More the rest of the Nerd Herders and Morgan are finishing up the last of the broken computers when Tang comes in with a cart full of more broken computer parts. Everyone tries to bail but Morgan convinces them to do it for Chuck, and if that isn't enough, to do it so that Harry Tang won't become their boss. The latter motivates them to go back to work.
Back at the auction Sarah and Chuck are walking around and while trying to eat an Hor D'oeuvre he spills soy sauce on his tux. In the bathroom he sees the same British man who was last seen with the painting and sees the La Ciudad CIA paperwork. He goes straight to Sarah to point out the man as La Ciudad. The man obviously suspects Chuck of knowing something and watches him carefully. As Sarah and Chuck go into the art gallery she tells him to go wait over at the bar while she does spy stuff. The bartender turns out to be Casey. A man shouts out Chuck's real name and turns out to be an old acquaintance from Stanford. He brags about being too young to retire but too rich to work while Chuck over glamorizes his Buy More job by saying that "I may be getting a managerial position at an electronics conglomerate." The man offers Chuck his card and Chuck flashes on it and says out loud the information he saw about how the guy was involved in illegal insider trading and had off shore accounts. This makes the guy assume Chuck works for the SEC, snatches his card from Chuck and runs away. While this is going on Sarah is seen chatting with the British man Chuck identified as La Ciudad.
Back at the Buy More, everyone is sitting around eating pizza and talking bout Chuck and his unusually hot girlfriend. Lester thinks something is off and Jeff suggests that she is a prostitute. Morgan tells them to stop talking about it and to get back to work when he accidentally locks himself in the caged off storage space where all the computers are. The door is broken and only Harry Tang and Chuck have the key that will open it. The Nerd Herders proceed to leave Morgan alone with the computers, that according to him, "freak me out!"
An increasingly drunken Chuck asks for another drink from Casey when Casey sees Sarah get pushed out of the room with a gun pointed at her back. He hops over the bar to follow them and tells Chuck to "Stay!" Chuck is drunkly offended and gets up to move around the room where he sees the water lilies painting but with a different frame than the one in the pictures.
A beautiful woman comes up and starts to make small talk about the painting with Chuck. When he mentions that he is more interested in the frame she looks at him in a calculating way. The two start to drink wine while looking at the painting when music starts to play and the woman asks Chuck to tango. Chuck has unfortunately learned the girls part of the tango from Captain Awesome. Up on the roof Casey is hiding in the stairwell waiting for the right time to strike as La Ciudad points a gun at Sarah, demanding to know who she is and who she works for. Casey jumps in and shoots the henchmen and Sarah breaks free. They declare that they are federal agents and then the man declares he is a member of MI6, the British Secret Service. He is not La Ciudad. He has been tracking La Ciudad through five countries. He says that they had intercepted a painting with plutonium in the frame and decided to let things proceed so they could catch La Ciudad with a fake painting. Which now raises the question... who is La Ciudad? At that moment the tango is fishing. When the beautiful woman dips Chuck he sees a scar on her neck which causes him to have a flash and he realizes that this WOMAN is La Ciudad.
Morgan has been calling Chuck nonstop and finally calls the place the auction is being held at. He ends up having his cover blown right in front of La Ciudad who has him escorted out of the room at gun point. Sarah and Casey go running back to the auction to find Chuck but find him gone. At that moment Chuck is in a hotel room tied to a chair being threatened with torture and death by La Ciudad. They pick him up to throw him out the window when he screams out that he thinks the painting is a fake and they set him down. He explains how the painting has a different frame so he thinks it is a fake painting and then La Ciudad points a gun at him and asks him how to fix a computer. Outside Casey and Sarah are following the tracking device in Chuck's watch. Inside the room Chuck has started to bore the occupants with a very detailed description of how to fix a computer. They believe him but since Chuck has seen her... she has to kill him. At that moment Sarah and Casey burst in, the henchmen fire back. La Ciudad jumps to the balcony below where Chuck's old Stanford acquaintance is crying to someone about the SEC knowing everything. He screams when he sees the woman break into his room and one of the henchmen go flying past the window to the ground. Sarah and Casey untie Chuck as La Ciudad and the one remaining henchman escape and vow to "take out" Chuck.
Finally at home Chuck walks in to see Ellie asleep on the couch waiting for him. When he covers her up she wakes up and has a bunch of questions about Sarah and the whole relationship. None of which he can answer. He kind of blows her off leaving her a little hurt and confused as to why he wont talk to her about this. She tell hims about Morgan's situation and he goes over there to save him. He send Morgan home and decides to finish the computer work alone and thinks it would be nice to do something he is good at, i.e. not spy stuff.
Morning comes and right as Chuck finishes Big Mike comes in to see if Chuck is finished. He expresses surprise that Chuck actually completed it in two days since it wasn't really a deadline that had been given but an incentive. Then he looks lovingly at his cookie before taking a bite, while Chuck humbly explains that his team did most of the work. Big Mike tells him that the first rule of management is to always take credit. At that moment Harry Tang walks in with empty cans and tells Big Mike that people have been drinking in the store. Big Mike tells Tang to loosen up and Chuck that while he needs to keep it out of the store, he gets extra points for (still in his tuxedo).
As Morgan tells of his horrific night trapped in the store, Casey approaches Chuck to tell him what has happened based on the events of the previous night. It seems like the federal government was going to catch La Ciudad and all is going to be fine. Case closed. Then Chuck sees La Ciudad's henchmen walk into the Buy More and ducks. Tang sees him hiding when one of the henchmen ask Tang if he can show him where Chuck is. Tang gladly does so but Chuck as already crawled away.
Outside a delivery woman (La Ciudad) walks, with a long package, walks past Sarah... both of them realize the others identity. Sarah ducks and contacts Casey. Casey has already seen the henchmen and is tailing one of them. Chuck tries to lead them off his trail by using the intercom to announce to the store that he is in the storage cage. One henchman asks Casey where the storage cage is and Casey says he will take him there. La Ciudad has climbed to the top of Wienerlicious and is building a sniper rifle as Sarah starts to climb up. Morgan points out where Chuck is hiding to the other henchman and Chuck flees. Casey beats down one of the henchmen in the refrigerator section while Sarah and La Ciudad fight on the roof. Chuck scrambles into the back room closely followed by the henchman, who walks right into the cage. Chuck closes it on him but the henchman opens it right up. Apparently it had been fixed. As the henchman aims to shoot Chuck a microwave collides with the henchman's head, thrown by Casey. Outside Sarah finally beats La Ciudad.
Back at the Bartowski residence, Chuck tries to explain to his sister why he can't talk about Sarah with her. He tries to find a way to talk to her about it and it turns out his sister just wants him to be happy and only wanted to know if he was truly into Sarah or not. After a nice family hug, the door bell rings. Both Morgan and Sarah are at the door. As Chuck walks Sarah to her car he tells her about his frustrations with doing all this spy stuff but having no one know what he is really doing, how he still has to work at the Buy More, and how he doesn't really feel like a hero. She says he is and that both he and she knows it. They discuss how if they were really dating they would kiss right about now but try to talk about it like it isn't desirable and then Sarah abruptly walks away. Morgan walks out and makes a comment about how creepy Casey is, as Casey is peeping at them through the blinds of his own apartment across the court yard. Then they head back inside.