Durarara!!
Mikado Ryugamine moves to Ikebukuro at his friend’s invitation and quickly becomes entangled in the city’s dangerous underworld. After witnessing the legendary Headless Rider, he finds himself caught up in escalating violence and gang conflict that begin to throw Ikebukuro into chaos.

Season 2 · Episode 30 ·
In For a Penny, In For a Pound
Izaya is overjoyed at Mikado’s behavior, which has greatly exceeded his expectations, and grows more excited at the future uproar he is ushering in. Masaomi and Chikage talk through things, while Saki and Anri break the ice.
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Episode 30 of season 2 of Durarara!!: “In For a Penny, In For a Pound”. Aired 2016-02-13. Watch it online free on ZapFlix.