For the first time, we see Billy sitting in Madolyn's office and talking to her about his feelings. It looks like she's his court-appointed counselor. Then we flash to him pulling some more violent jobs and sitting alone at home looking at old photos.
In Madolyn's office, Billy tries to explain how hard it is to work beside a mass murderer all day. His heart is racing, but his hand is always steady.
Back in his apartment, Billy takes a handful of Oxycontin pills, which means he's probably drugging himself pretty heavily to stay calm while doing jobs for Costello.
It's been a year since Billy went undercover, and he's had enough. He's clearly burnt out, and his brain is starting to go on him. He wants to know why Queenan and Dignam haven't made a move on Costello yet, since Billy can connect him to dozens of felonies.
But Queenan and Dignam say they're still building a case. They also mention that they think Costello has a spy inside the special investigations unit, which only freaks Billy out even more.
Back in Madolyn's office, Billy says he wants Madolyn to give him Valium to help him sleep because he's going nuts with insomnia. But Madolyn is skeptical; she thinks he's using her to get drugs.
After Billy storms out, Madolyn runs after him to give him a prescription and tell him she's transferring him to another counselor. Things calm down between the two of them, and Billy asks her out for a cup of coffee. Yup, just like that.