Checkmate follows the main character, October, a villain named Vengeance in a futuristic America. Join him on his journey through mental health issues and his struggle with being a black gay man in a society that wants nothing to do with him. He meets a hero named Sunburn, or Vivaan, and their relationship progresses from hatred to a strange loyalty to true attraction. After they mutually decide they no longer hate each other, the two find themselves in a two year long relationship, heading to Vivaan's home country of Germany for a Christmas celebration with his family. After the holiday ends poorly in a car crash, October gets captured by another hero while avenging his family's murder. After escaping, October's close friend tricks him into abandoning his boyfriend, hurting them both emotionally, before a friend inevitably gets them back together.