Mafia Boss Takes High School Episode 1 begins with an interesting twist. Will is on a second date with Jane. But he's concealing his real identity from her as a Mafia lord but she gets curious. Trying to get her coffee, he mistakenly bumps into Jerry, a commoner, who begins to humiliate Will. When Jane intercedes on his behalf, Jerry even lays his hands on her. But what happens next when Will beats Jerry up and pulls out his men to aim their guns at him?