Based on a manga itself, Tokyo Loser is about Natsumi (Kie Kitano) who moves to Tokyo from the countryside to enter an arts' university and become a recognized manga artist. In Tokyo, Natsumi meets Ryosuke (Sosuke Ikematsu) and they are soon a couple except the relationship is cut short owing to the latter's lack of money. Natsumi has to get a job as she struggles with her slipping dreams. Written by aghaemi

Yuri Kashiwaga was once known as a genius pianist. One day, she returns to her hometown in Goto Islands from Tokyo. There, she begins to work as a temporary teacher at a middle school and advisor for the school chorus. The chorus aims to take part at a competition. Yuri gives the members of the chorus members an assignment. She instructs them to write a letter with the title of "To myself 15 years later." The 15-year-old boys and girls write about their secrets and worries.

Tadashi Imamura is a burglar who idolises Ozaki, a star baseball player he shares a birthday with. One day he realises their connection is much deeper than that and decides to find out more. Based on a short story by Kotaro Isaka.

Hibino Tsubaki (Takei Emi) is a young teenage girl with a talent for styling other people's hair. Yet, Tsubaki suffers from low self-esteem and isn't very comfortable styling her own hair. She also has a tendency to dress old-fashioned. She's teased at high school because of this. One day, popular male student Tsubaki Kyota (Matsuzaka Tori) targets Tsubaki for teasing. Tsubaki Kyota holds sway over the entire classroom and is quite a playboy. Inexplicably they fall in love. Meanwhile, Tsubaki Kyota has commitment issues...

Set in Shizuoka and Tokyo, Japan in the late 1980's. Takkun (Shota Matsuda) is a university student in Shizuoka attempting to find a job. Mayu (Atsuko Maeda) is a dental hygienist. They meet through a blind date and begin to date, but Takkun finds a job in Tokyo and goes there. They begin a long distance relationship, but their relationship breaks down.

Seijiro Ito possesses good looks, but also has an overinflated ego. He gets involved with five different women. Rio Yazaki is one of the women involved with Seijiro Ito. She wants to revive her career as a screenwriter, by using other people's unhappiness.

Yukihiko Nishino is very popular with women, but, in the end, he is always dumped by a woman. Yukihiko seeks out his true love.

Nobuto Urita is a boxer, who loves his sport more than anything. No matter how hard he tries, Nobuto Urita keeps losing his matches. Meanwhile, Kazuki Ogawa spars with Nobuto Urita at the same gym. He is a boxer with elite talent and skills. Unlike Nobuto Urita, Kazuki Ogawa will likely win a championship. Kazuki Ogawa is also engaged to Chika Amano. She is a childhood friend of Nobuto Urita and also his first love.