An adventure in another world with cute girls by your side and video game-like powers—sounds like an anime fan's dream, right? Not so for melancholic author Osamu Dazai, who would quite literally prefer to drop dead. Video games haven't even been invented yet when he gets yanked into another world in 1948. Really, all the fantastical adventure he keeps running into is just getting in the way of his poetic dream of finding the perfect place to die. But no matter how much he risks his hide, everything seems to keep turning out okay. Follow a miserable hero like no other in this cheerfully bleak isekai comedy!

In spite of his best time-leaping efforts, Takemichi Hanagaki continuously fails to prevent the present-day death of Hinata Tachibana, his adolescent love. The adult Takemichi grapples with grief and the ramifications of the Tokyo Manji gang's criminal empire—an unintended product of his timeline meddling. Though the gang once operated under the idealistic Manjirou "Mikey" Sano, it has now been taken over by the malicious Tetta Kisaki and, as a result, has abandoned its original optimistic intent. Despite feeling hopeless, Takemichi travels to the past once again to investigate Black Dragon, a rival motorcycle gang whose actions ultimately lead to Hinata's demise. There, he meets the young Hakkai Shiba, a fellow gang member whose older brother, Taiju, tyrannically rules Black Dragon. When Taiju brutally beats Takemichi in a one-sided street brawl, Hakkai attempts to withdraw from Tokyo Manji in apology—an act that Takemichi must prevent to spare Hakkai a grim future. Through a shared tragedy, Takemichi bonds with Chifuyu Matsuno, establishing a close comradery both boys desperately need. With Chifuyu on his side, Takemichi works to unravel the fates of Black Dragon's members, fighting to create a happy future for his loved ones.

High school student Misumi Makoto is called into a fantasy world by the god Tsukuyomi, in order to be a hero. However, powerful others in this world aren't as thrilled to have him there, and they kick him to the edge of the world just as Tsukuyomi declares that he must leave Makoto to find his own way. Now it's up to Makoto to find his own way!

Since the death of his parents, Shinpei Ajiro had lived with the Kofune family and their two daughters—Mio and Ushio. Although he then left his home island to continue his education in Tokyo, Shinpei returns after Ushio tragically drowns during the attempted rescue of a little girl. During the funeral, his best friend informs him about bruises found around Ushio's neck, casting doubt over the cause of her death. Suspecting a murder has taken place, Shinpei reevaluates recent events, but strange incidents only continue to transpire. Disappearing people and other unexplainable occurrences lead Mio to recall an old folktale referring to entities called "Shadows," which may not be entirely fantasy. Supposedly, an encounter with one's Shadow foretells the person's impending demise. Facing the dark side of Hitogashima Island, Shinpei stands against his grim fate to fulfill Ushio's final will—to protect Mio.