The movie follows a girl in her early twenties named Izzy Howard (Lola Morgan), who wants to be a great writer. Yet her hypersensitivity to the competitive energy of her roommates Ursula (Alexandra Warrick) and Selma (Meredith Casey) inhibit her success. Izzy and Ursula are both students in the same writing seminar at Columbia University. Selma studies acting at Juilliard.
In a writing seminar, Izzy and Ursula’s professor, Greg Benson (Thoeger Hansen), tells a story about how he survived a near-death experience because he was destined to be a writer. Izzy feels both frustrated with Greg’s ego and unimpressed with his work. Ursula, on the other hand, has a crush on Greg. After class Ursula gets a phone call from Selma, asking if she wants any pills because she has an appointment with a psychiatrist. During the phone call, Selma lies in bed with Lenny (Michael Ford), an actor also studying at Juilliard who was recently cast as Jocasta in a gender-bending production of Oedipus Rex. Lenny overhears the phone conversation and asks Selma if she can get him Vicodin, because he has to wear heels for the production, and his foot hurts. She reluctantly agrees.
Influenced by her professor’s story about destiny, Izzy visits a Tarot Witch (Greer Morrison), who can tell right away that Izzy is depressed and has always had trouble fitting in. The Witch says that this is because she’s an indigo child, which means she belongs to a chosen generation that will have to be strong when “heavy shit goes down” during her lifetime. The Witch offers Izzy a more elaborate reading for the price of $25. Izzy declines because it’s out of her budget. Instead she bargains for a $5 Tarot Special. The first card The Witch pulls from her Tarot deck has a picture of a skeletal figure holding a scythe, with the word “Death” written underneath.
Izzy returns to her apartment with two items: a bottle of Tanqueray and a small green Tarot Book. Her roommates act concerned. Izzy passes out on the couch, cradling the bottle of liquor. She wakes up to the sound of knocking on the door, gets up, and looks through the peephole on the front door. She sees Lenny in his Jocasta costume. Confused, she goes back to bed. Selma comes to the door in a bathrobe and gives Lenny a canister of Vicodin in exchange for a wad of cash. She also invites him to spend the night. They have violent-sounding sex, which Izzy overhears from the other room.
Izzy spends the night on the floor of the living room, passed out with the Tarot Book open on her chest. She is woken abruptly up by Selma, who’s mad because Izzy stole some of her Valium. Izzy says the reason she stole it was because she was having night terrors. Ursula comes into the room and tells her to get dressed for writing class. Izzy tells her she’s not going; she’s decided to drop out of college and write a novella. Her roommates are not supportive, and leave her alone to go chat in the bathroom. Ursula suggests that Izzy might be schizophrenic. Selma says no, no, no; Izzy must have seen Lenny in his costume. Then she tells Ursula she has a plan “to help Izzy.”
On campus at Juilliard, Selma asks Lenny if he’s willing to come back to the apartment costumed as the Grim Reaper to trick Izzy into thinking she’s had a near-death experience. Lenny is reluctant to get involved because he thinks Selma is doing it just “to be a bitch.” Selma says that Izzy has a tendency to blend fantasy and reality, so this might be the only way to effectively intervene with her reckless behavior. She also insinuates to Lenny that if he agrees to do his, she’ll reward him with sexual favors. Lenny considers this.
At night, Izzy works on her book while Ursula attempts to write an essay for Greg that’s due the next day in class. Selma comes home with a bag from the drugstore containing various canisters of pills. She and Ursula leave the apartment together to go out to a restaurant in Brooklyn. They make a point of leaving Izzy alone. Immediately Izzy takes the pills and blends them with Tanqueray. She passes out on the couch. In the middle of the night, Lenny (disguised as Grim Reaper) climbs through the window. He and Izzy exchange few words, though it seems like they’re about to do the nasty. A montage renders Manhattan barren-and-lifeless at night.
The next morning, Ursula finds Izzy sleeping on the couch alone with pages from her book strewn around her. She picks up a few pages and brings them to her writing seminar, where she presents them to Professor Benson as if she wrote them. Greg says he’s very impressed with her work and offers to give Ursula writing advice. Awkwardly, he touches her on the arm. Ursula returns to the apartment and finds Izzy distraught, because she can’t find the notepad that contains her writing. She asks if Ursula’s seen it; Ursula says no. An air of distrust has set in between them. Ursula goes into the hallway and calls Selma on the phone.
Selma answers Ursula’s phone call in the middle of a hook-up at Lenny’s place. It turns out that Ursula didn’t call for Selma, but for Lenny. That night Ursula and Lenny meet on an abandoned street. Their exchange feels fractured. Ursula explains the situation: Izzy’s writing a book, and Ursula is eager to read the whole thing, so she wants Lenny to sneak back into the apartment and steal the rest of it. Lenny seems vaguely suspicious of Ursula’s motives. Then Ursula says something about “getting laid.” Lenny shakes her hand and says he’ll do it.
That night Lenny returns to the apartment in his costume. He finds Izzy awake and waiting, having just taken a fresh dose of liquor and pills. He starts to kiss her (awkwardly) but she pulls away. Izzy says she doesn’t feel like giving him a blowjob. Lenny says that’s OK, because he’s only there to talk about the pages of her book. Izzy seems relieved that he’s the one who took them as opposed to her roommates. She asks if he read them; he lies and says yes, and that he wants to read the rest of it. Izzy says she’s never had someone ask to read her writing and that it seems too good to be true. She tells Lenny that she thinks he’s a hallucination, a projection of her own fantasies, and that’s the only reason he had slept with her in the first place (because she’s “not a stone cold fox in the sexual department”). Lenny continues to flatter her with fake compliments. Finally Izzy gives in and hands over her manuscript. She says he doesn’t have to read it right there and then, and kisses him.
Back in writing class, where Izzy’s still absent, a heated debate takes place regarding The Bell Jar by Sylvia Plath. One student named Jones (Gabriel Schwartz) holds the opinion that Plath only killed herself to be dramatic. Greg seems to side with Jones, while the girls in the class disagree with him. Ursula gives a passionate defense of Plath, saying that she was such a great writer that it doesn’t matter “how much of a cunt she was to her friends.” Greg appears shocked by Ursula’s choice of words.
Ursula rushes to Selma, and asks if Lenny’s handed over the manuscript yet. Selma says no and asks Ursula why she cares so much. Ursula explains that she made a fool of herself in front of her professor, and thinks if she hands over the manuscript, he might be more forgiving. She also tells Selma that she thinks she’s the main character of Izzy’s book. Now Selma is interested. So the two of them wait outside of Lenny’s rehearsal to get the manuscript from Lenny. He exits holding the pages in his hand. Selma asks for him to hand it over, but he refuses, because it contains sensitive material. Ursula takes it from his hand. She and Selma run away with it.
Izzy returns to the Tarot Witch to ask about the mysterious visit by the Grim Reaper. The Tarot Witch says she’s never heard of that happening before. Izzy says it’s possible that she was just strung out on liquor and pills. The Witch says that any boy who calls himself the Grim Reaper might not have the best motives, and suggests that Izzy consider how much she’s willing to sacrifice for a boy.
In a park by the waterfront, Ursula and Selma read pages of the manuscript and try to figure out which of them is the basis for a character named Selena. It seems like Izzy has intense feelings toward Selena. Ursula wonders aloud whether Izzy’s a lesbian. Selma notices that Izzy keeps obsessing about how beautiful Selena was. Then Ursula points out that she describes Selena as “slender,” which she thinks could only apply to her and not Selma.
That night, Selma binges on cheese; Ursula picks at a bar of dark chocolate; Izzy eats from a can of sardines. Selma says that she once read on a diet blog that a woman’s attitude toward food says a lot about her sex life. She and Ursula turn to Izzy and insinuate that what she’s eating — fish — must mean she’s not straight. Annoyed, Izzy goes into the other room, where she assesses her own appearance in a mirror. She seems really insecure.
Selma goes back to Lenny’s apartment. He tells her that sex with her is more satisfying than with Izzy. Selma appears both unconvinced by Lenny’s flattery, and suddenly guilty about the whole situation. She tells Lenny that she thinks they should stop hooking up. Lenny seems irritated. Then Selma asks if it’s OK for her to bring her roommates to see his production of Oedipus Rex that night; Lenny says that’s fine. Selma leaves him alone.
Izzy goes back to writing seminar and reads a poem to the Grim Reaper that implies she’s suicidal. After class, Greg hands her a card for a therapist he knows and recommends. Ursula waits for Izzy in the hallway after class. On his way out of the building, Greg runs into them both and asks Ursula about the book she’s writing. Izzy appears to figure things out, though Ursula doesn’t notice. Ursula says that the guy she wrote the poem for sounds like an asshole. She invites Izzy to go see Oedipus Rex with her and Selma that night.
At the show Lenny delivers a monologue from Oedipus Rex, in which Jocasta tells her son to beware of the malignant goddess Ambition (“for she’s a foe to justice”). The girls wait for him afterward and congratulate him. Izzy, looking especially worse for wear, tells him he was good. Lenny says thanks but acts like he doesn’t even know her. Ursula and Selma invite them both to dinner in the meatpacking district; Lenny says no. They leave without waiting for Izzy. By now Izzy feels so disheartened about the future, so disgusted with her own looks, and so hurt by the betrayal of Lenny and her roommates that she commits suicide by stepping into oncoming traffic.