Chiaki Konoike is a character who appears as the girlfriend of Bob Makihara. She is a student of Toudou Academy and is noted for having a very open-minded personality. Information regarding her background prior to the events of the story is not available. Her motivations evolve throughout the narrative. Initially, she does not object to Souichiro Nagi and Bob Makihara’s street-fighting lifestyle. However, she opposes them after they join the Juken Club. Her perspective shifts again after hearing the story of the past relationship between Maya Natsume and Mitsuomi Takayanagi. She comes to believe that Maya’s ego and stubbornness are the causes of misery for those around her. Following a fuller explanation of the past from Bunshichi Tawara, Chiaki decides to offer her support to the Juken Club, though she still holds that Maya’s stubbornness was a key factor in the events that transpired.

Chiaki is central to a specific traumatic event in the story. After Ryuuzaki decides to give Souichiro and Bob an "Unlimited Punishment," Chiaki is raped by him in the manga, while the anime depicts this as an assault. Her key relationship is with Bob Makihara, whom she refers to as her boyfriend. The nature of their relationship is portrayed as openly physical, with Chiaki frequently depicted in intimate situations with Bob, even suggesting he quit school so they could spend all their time together. No information is available about her notable abilities or fighting skills. Information about her character development is limited to the change in her stance toward the Juken Club described above.