As the school year progresses, Mikado tries to adjust to the city life by trying new things and becoming a different person. Anri tries to cope with the loss of someone close to her but gets cornered by a group of thugs. It's up to Mikado to save her with the help of a few people he was warned to stay far away from.
Opening Theme Uragiri no Yūyake ( 裏切りの夕焼け Sunset of Betrayal") by Theatre Brook
As Simon tries futilely to draw in customers for the Russian sushi restaurant where he works, a pair of Russian tourists ask him for directions. After sending them on their way, asking them to come again, Simon muses on the ever-changing nature of Ikebukuro. Mikado homeroom teacher asks for volunteers for male and female class representatives. Anri volunteers, and after some internal debate, Mikado does as well. After class, Mikado tries to engage Anri in conversation, but she hurriedly leaves after seeing the teacher Takashi Nasujima approach. Masaomi playfully teases Mikado about his obvious infatuation with Anri, then drags him along to hit on girls.
In the city, Mikado watches as Kida is shot down by a trio of young women, one of whom tells the others that their friend is dating someone from the Dollars. They argue over whether the Dollars are as violent as the other color gangs that have plagued Ikebukuro, and if the recent series of murders has anything to do with the group. Mikado remembers "Kanra", a friend of his online, discussing the Dollars and their possible connection to the Chinese mafia and other crimes. Afterwards, as Masaomi blames Mikado's gloomy attitude for his failure to attract any women, they run across Kadota, Walker, and Erika as the trio make their way to a book signing. Mikado asks them about the Dollars; Kadota says that they are dangerous, and warns Mikado not to get involved or ask too many questions.
Elsewhere in the city, Simon continues to unsuccessfully market the sushi restaurant. As Shizuo Heiwajima and Tom Tanaka look for a place to eat, Tom is spooked by the sight of the Headless Rider passing by on her black bike. Seiji Yagiri looks for the woman he loves as Anri runs across a young woman who looks somewhat like her missing friend Mika Harima and excitedly catches up to her; embarrassed by her mistake, Anri runs away.
Mikado and Kida continue to walk the streets, both somewhat glum. Mikado muses on the Dollars, while Kida sees a group of young men wearing yellow scarves and is unsettled. Partly to cheer himself up, Kida gives Mikado a flamboyant pep talk. Soon afterward, they come across Anri being bullied by a trio of ganguro girls, accompanied by a thug named Hiroshi, who claims he is a member of the Dollars. As Mikado prepares to rescue her after anxiously considering the ramifications of doing so, Izaya Orihara shows up and forces him into action by shoving Mikado into the fray.
As Mikado moves to Anri's side, Izaya intervenes, stating that while he cannot hit a girl, he is more than capable of stepping on their cell phones. He takes one from one of the girls, then stomps on it while laughing maniacally. The thug Hiroshi steps forward, groping himself threateningly through the crotch of his pants. Hiroshi throws a punch at Izaya, who sidesteps and shaves Hiroshi halfway bald in a single swipe of his switchblade. Hiroshi and the ganguro girls flee the scene.
In a less dangerous section of town, Izaya teasingly praises Mikado for coming to Anri's aid, and congratulates him for getting into Raira Academy. Kida asks Izaya why he is in Ikebukuro, and Izaya answers that he came to meet someone. As he looks at Mikado and mentions that he has accomplished what he came for, a convenience store trashcan hurtles through the air and hits Izaya in the face. Shizuo, smiling and visibly furious, asks Izaya what he is doing in Ikebukuro. After a bit of conversation indicating that Izaya has wronged Shizuo in the past, the pair's confrontation is interrupted by a crowd of thugs looking for Izaya, led by Hiroshi. They are surprised by the presence of Shizuo and, panicked, one of them attacks him from behind. This makes Shizuo even angrier, and he punches the thug, who flies through the air, losing most of his clothing in the process, and slams into the pavement some distance away.
Mikado sees why one should not cross Simon or Shizuo
Izaya takes advantage of the ensuing chaos to make his escape. Shizuo notices Izaya fleeing, and tries to stop him by ripping a vending machine from where it is bolted to the street and throwing it after him. Simon leaps from the upper stories of the office building where he was delivering sushi and catches the vending machine after reaching the ground. He then catches Shizuo's punch, chastising him for fighting. Noting Anri's fear and alarm, Mikado grabs her hand, and the pair run from the scene, with Kida not far behind. After catching his breath in front of a fountain, Mikado realizes that he is alone with Anri, and tries to take advantage of this by talking to her, but she cuts him off, thanks him, then runs away.
Later that night, Izaya walks the streets, pleased with himself as it turns out he was looking for information on Mikado. On the roof of an unidentified building, Shizuo sits with Celty, voicing his frustration at once again missing his chance to get rid of Izaya. Simon, worn and torn from his off-screen fight with Shizuo, continues to try and draw in customers for the sushi restaurant.
The episode is narrated by Simon, albeit without his Russian accent.