After one of his coworkers fails to repay a debt, apathetic bum Kaiji Itou is pressured by loan sharks to settle the large sum of cash. Since Kaiji has little money and no future prospects of his own, he is unable to return what his colleague borrowed. Faced with massive financial burdens, Kaiji is given an offer to board the illustrious Espoir—it is said that one night aboard the ship, and all of your debts will be paid. What seems like a simple night of gambling quickly turns into a game of strategy and betrayal. With the losers of the tournament being subjected to a backbreaking life of indebted servitude, Kaiji must choose his actions—and allies—carefully. However, this is only the beginning of a series of gambles that will wager Kaiji's life, testing the full extent of his wits and will to survive.

Life is not going well for 28-year-old Kyouya Hashiba. Having left his office job to pursue a career in the video game industry, his internship at a popular game studio abruptly ends, leaving him unemployed and forcing him to move back in with his parents. Additionally, his jealousy toward the success of the Platinum Generation—a group of similarly-aged creators—has caused him to regret his decision to attend a traditional university instead of an arts college. Even though he believes there are no second chances in life, Kyouya is suddenly given one when he wakes up one day and finds himself 10 years in the past. Instead of choosing business school like he originally had, Kyouya decides to pursue his passions and attends the Oonaka University of Art. There, he meets classmate Eiko Kawasegawa, the woman who had hired him as an intern in the present, alongside his new housemates and future Platinum Generation members: underachieving artist Aki Shino, aspiring singer and actress Nanako Kogure, and naturally-gifted writer Tsurayuki Rokuonji. With each project they complete together, Kyouya and his friends venture closer to discovering their true potential as creators and remaking their lives into the ideal versions they desire.

At a certain trading company, saleswoman Futaba Igarashi has managed to hold her respectable job for almost two years thanks to the guidance of her senior coworker—Harumi Takeda. However, due to Igarashi's short stature, Takeda often teases her and treats her like a kid, leaving Igarashi constantly annoyed by his antics. Despite this, Igarashi notices Takeda's reliability as he is always ready to help whenever something at their workplace goes awry. As Igarashi and Takeda spend more time together, their relationship soon develops further than simply being coworkers at the office.

Itsuki Hashima is a light novelist obsessed with little sisters, strictly focusing on them when he writes his stories. Despite his personality, he is surrounded by a tight circle of friends: Nayuta Kani, a genius yet perverted novelist who is in love with him; Haruto Fuwa, a fellow male author whose work has seen considerable success; Miyako Shirakawa, a good friend that he met in college; and Chihiro, his perfect younger step-brother who takes care of the housework and cooking. Together, they play strange games, go on spontaneous journeys, crack silly jokes, and celebrate each other's successes. However, each individual must also deal with their own issues, whether it is struggling to meet a deadline or coming to terms with traumatic events buried in their past.