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Lilly is James's girlfriend while they're in rehab. They sneak out into the woods, breaking all the rehab rules, just to be with one another. So it must be love, right?
Well, it's more like another addiction. James is replacing his dependency on chemicals and alcohol with an addiction to Lilly. When they lock lips, he writes that she "Kisses me kisses me I am high" (3.1.227). Lilly: "Sorry, there's a little coke on my gums." Just kidding.
At least James gives Lilly a name, unlike the nameless girl he was infatuated with (the one he stared at for three years). Lilly is 22, she's from Phoenix, and her mother was a heroin addict. After dealing with tons of abuse, she moved to live with her grandmother in Chicago. That's the same Grandmother who thinks James is cute and later gets sick with cancer.
That's about all we get to find out about Lilly, though she does play a small role in James's recovery, like that time she whispers "You're okay" (2.3.293) to him over and over in the woods. She also tells him to respect his parents... and he does, which makes us wonder: does it invalidate his apology to his parents if he's only doing it because Lilly told him to?
When James and Lilly are finally caught, Lilly runs away from the clinic. James chases her to a crack house and saves her, very publicly not smoking crack in the process. Everyone is so amazed that James managed not to do crack while he was in the crack house that they pretty much give him a free pass to leave the clinic.
Does James really love Lilly, or does he mostly see her as a way to prove himself, which is what he cares about most? Is it strange that Lilly is relegated to a footnote at the end? All we know is that she commits suicide the day James gets out of prison. Are we supposed to think things would have been different if James had been there to save her? Is this a good thing or a bad thing? Was James a positive influence in her life? Was she a positive influence in his?