Lip's Season 8 journey focuses on the struggles surrounding his sobriety. He seeks safe harbor in the arms of Sierra, who has chosen to reconcile with her son's father, Charlie. Lip takes umbrage with this idea and attempts to sabotage the relationship by sending Charlie a pizza with a packet of cocaine on top. The men run into each other at an AA meeting a few hours later, and Lip immediately feels guilty when he hears how Charlie struggled to avoid the temptation. So Lip tries to reverse the damage by breaking into Charlie's apartment to steal back the coke — only problem is he gets attacked by Charlie's dog and drops his fidget spinner on the way out. Charlie, however, thinks Lip heard the story and broke in to help him out.
Convinced that Charlie is sincere in his efforts with Sierra, Lip focuses his energy on helping Professor Youens get sober after his fifth DUI — yes, this is the one where his teacher crashes a car through a family's living room — but Lip isn't very successful as the professor seems determined to let the alcoholism take its toll. At Youens' funeral, Lip learns that he wasn't the only special student in the professor's life. Hurt by the realisation, Lip returns to the teacher's apartment to find a letter that outlines exactly how much Lip meant to the man.
Feeling alone and in need of love, Lip ends the season by taking on the brave responsibility of caring for the niece of a former coworker.