Season two starts off with Molly deciding to focus on her career rather than her love life. After accidentally getting the pay stub of her white coworker Travis, Molly learns that he makes more money than her, despite not being nearly as good at his job as she is. She starts looking into transferring to the Chicago office of Merrill, Johnson, and Schwartz after a colleague does so and she connects with a visiting lawyer, Quentin (Lil Rel Howery). She also sees a therapist on and off, who attempts to crack through her defences and confront Molly about her obsession with life looking a particular way.
Though Molly briefly dates a man she meets at a club — Lionel, played by Sterling K. Brown — she stops seeing him because she doesn't feel the spark. As she continues to waffle on the decision to transfer offices, she begins spending more time with Quentin, eventually sleeping with him. She admits that Quentin is a great guy who could be good for her, but she decides not to continue seeing him because she can't help but be self-destructive.