In 2008, upon learning of his father's role in the second shooting of Kate Howard and his sister's marriage of convenience to Sonny, Johnny decides to sever all ties to his family business. He moves in with new roommates Lulu and Maxie, and begins to search for a job. With no further education since high school and his known association with the mafia, Johnny finds no one willing to hire him, and during his job search he is arrested. Johnny's frustration over finances and guilt over his role in Michael's coma lead him to contemplate ending his relationship with Lulu. He also considers having sex with Maxie, when they are snowed in at his garage, to make sure the split is permanent, but the two are unable to go through with it. Eventually, after accompanying Maxie to an event representing Crimson, he takes Kate's offer of $1,000 per event as Maxie's official Crimson escort.
Maxie and Johnny miss another date to a club opening for Crimson to help Claudia get Ric's stomach pumped after she drugged him. Due to this, Lulu got a call stating Maxie and Johnny never arrived, prompting Spinelli and Lulu to become suspicious. Spinelli confronts Johnny about the incident, stating he will fight for Maxie. Maxie called Johnny who told Maxie to make sure Lulu doesn't know what happened. Johnny confessed to Lulu that he and Maxie had almost had sex during the blizzard. He tells her that he wants to be free to be who he is and that he doesn't want to have to apologize for everything that he does. He and Maxie later meet at the dock where he begins his next move of self-destruction, telling her he wants to burn down his life and does not care, now that Lulu is out of it. He tells her that he wants her. Spinelli later catches Maxie and Johnny engaged in a kiss. He tells them to stop and shames them. Johnny explains that he broke up with Lulu and he told her what is going on with him and Maxie. Spinelli punches Johnny and Maxie stops them from fighting. Johnny leaves to give Maxie and Spinelli time to talk.