Character Analysis
Maura is will's friend from school who clearly likes him in a more-than-friends way. In fact, she likes him so much that she seems to overlook the fact that he is obviously totally not into her.
She's jealous of any interaction will has with other girls and annoyed when he won't open up to her. Of course, she doesn't help her case by snooping in his things, finding a bottle of pills, and then asking him to explain his problems. Not cool at all. She also ambushes him at work to ask if he's gay, which will does not appreciate one bit:
maura: are you gay?
me: what the f***?
maura: it would be okay with me if you were.
me: oh, good, because the thing i'd be worried about the most is whether you were okay with it.
maura: i'm just saying.
me: noted. now will you just shut up and let me work, okay? or do you want me to use my employee discount to get you something for your cramps? (4.2)
The weird part of this is Maura knows that will is gay. She knows this because she's been talking to him online as a boy for months now. Yes, Maura stoops so low in her obsession with will that she actually makes up a fake profile of a guy named Isaac, goes into a chat room that will frequents, and strikes up a super intimate relationship with him. It's pretty insane and pretty horrible.
will has rejected Maura in every way possible as a girl, but she likes him so much that she just can't let it go. So she pretends to be Isaac. Why on earth would someone be so cruel? And how could she tell him the truth in such a heartless way? We'll let her self-destruct in her own words:
maura: yeah, the album's called "isaac's not coming, you f***ing liar."
this is not good.
me: that's a pretty stupid name for an album […]
maura: i am isaac, will.
me: don't be stupid. he's a guy.
maura: no he's not. he's a profile. i made him up.
me: yeah, right.
maura: i did.
no no no no no no no no no no no no.
me: what?
no please no what no no please no f*** no NO.
maura: isaac doesn't exist. he's never existed.
me: you can't
maura: you're so caught. (8.18-20, 24-28)
Oh, Maura—you've pretend to be another person for months and betrayed your friend, but will is the real liar here? Sure he is… It's hard to disagree much with will when he tells us that Maura is a "f***ing witch ass b**** mussolini al-qaeda darth vader non-entity" (10.45). Girl has gone beyond the realm of bad behavior. So when will refuses to speak to her or even acknowledge that she exists, we totally get it. She betrayed him in the worst way possible and she totally deserves to be shut out by him forever and a day.
But is there any justification for Maura fronting as Isaac? Hmm… By the end of the story, will understands her a little better:
maura: you didn't mind me when i was isaac. when we would chat every night.
me: but that was a lie! a complete lie!
now maura looked me right in the eye.
maura: c'mon, will—you know there's no such thing as a complete lie. there's always some truth in there.
i don't know how to react to that. i just say the next thing that comes to my mind.
me: it wasn't you i liked. it was isaac. i liked isaac.
the blankness has disappeared now. there's sadness instead.
maura: ...and isaac liked you. (18.61-67)
Okay, so this doesn't justify Maura's super calculated deception, but it does show that will is starting to understand what drove her—and it wasn't malice half as much as a desire for will's affection and attention. She liked him and she just couldn't let it go without a fight. Her feelings as Isaac were genuine; that part wasn't a lie. In real life, Maura is a snarky goth girl who always looks on the dark side, but as Isaac, she's softer and more supportive of will. Isaac is exactly who will needs. Except he doesn't exist. At least not as a guy.
In the end, Maura might still be a rotten person who does a really rotten thing, but she is also forgiven. She and will aren't going to ever be friends again, but he also won't carry around his hatred for her anymore. They can both let things go and move on. And maybe that's the best possible outcome in a terrible situation like this one.