Sydney (or simply 'Syd') (Radha Mitchell) is a 24-year-old woman living in New York City who has her whole life mapped out in front of her. Living with longtime boyfriend James (Gabriel Mann), and working her way up at a respected high-art photography magazine called 'Frame', Syd has desires and frustrations that seem typical and manageable. But when a crack in her bathroom ceiling springs a leak and Syd finds herself knocking on the door of her upstairs neighbor to complain about the leak, a chance meeting suddenly takes her on a new path.
Opening the door to an uncharted world for Syd is Lucy Berliner (Ally Sheedy), a renowned photographer, enchanting, elusive, and curiously retired. Now age 40, Lucy lives with her once glamorous former model, heroin-addicted German girlfriend Greta (Patricia Clarkson), and plays host to a collection of hard-living party kids. Before Syd's caught her breath, she's caught Lucy's fascination and is drawn into the center of Lucy's strangely alluring life upstairs.
Syd mentions Lucy to her bosses (without realizing that she is famous) but they remain uninterested until they realize exactly who Lucy is. Syd then sets up a meeting with Lucy and her employers at a local diner where Lucy frequents. Lucy agrees to work for the magazine as long as Syd is her editor. Soon a working relationship develops between the two and a project is underway which promises a second chance for Lucy's career. But as Syd and Lucy's collaboration draws them closer together, their working relationship turns sexual and the lines between love and professionalism suddenly blur. As Syd slowly discovers the darker truths of Lucy's life on the edge, she is forced to confront her own hunger for recognition and the uncertain rewards of public esteem.
In a minor subplot, Lucy makes occasional visits to her estranged Jewish mother Vera (Tammy Grimes), whom is nearly as troubled and self-destructive as her daughter Lucy. Whereas Lucy takes recreational drugs such as cocaine and marijuana, Vera drinks and chain-smokes despite her own failing health. Lucy is open and honest about her sexual orientation to her mother who makes little effort to hide her conempt that her only daughter and child is a lesbian, but seem to half-heartedly accept it anyway.
Soon, James becomes more jealous about the amount of time that Syd is spending with Lucy, while Greta also feels the same with Lucy over her meeting with Syd. When Greta passes out and nearly dies from a drug overdose at one of Lucy's parties, she is revived by Syd of all people. Lucy tells Greta to get clean and quit drugs, but Greta refuses unless Lucy ends her business relationship with Syd. Lucy refuses, and Greta moves out to want some space.
Lucy then asks Syd to come away with her on a weekend getaway to get inspiration at her parents country house. When James finds out, he makes Syd choose between him or Lucy. He tells Syd that if she goes away from the weekend with Lucy, their romance will be over. Syd goes anyway.
During a road trip to the countryside and to the country house, Lucy and Syd talk about their own respective lives. Lucy then begins taking photos of Syd sitting in the car in casual poses. That evening at the country house, Lucy and Syd finally consumate their growing attraction to one another and they both sleep together. In the morning, Lucy takes more photos of a semi-nude Syd in bed and even takes a posted one of herself laying next to Syd in the bed.
Upon arriving back in New York the next day, Syd discovers that James has moved out, and Lucy finds likewise with Greta. Afterwords, Lucy gives the photos that she took of the various parties, as well as the photos that she took of Syd and asks to use them for Frame's latest cover. Syd shows the photos to her employers whom are not satisifed with them. Desprate, Syd then shows the photos of her that Lucy took of their weekend together as an alternate to the cover. She is then forced to admit that she and Lucy are now lovers.
One evening, Greta returns to Lucy's apartment wanting to get back together with her, but Lucy is hesitent to do so, aware of Greta's contining drug addiction. Greta then convinces Lucy to have one last drug binge together for old times sake.
The next morning, as Syd is on her way to work, she finds one of Lucy's friends, Arnie (Bill Sage), sitting in his car outside the apartment building. He tells her that Lucy died apparently from a drug overdose. Syd is filled with conflicting emotions over how to react to it, but Arnie tells Syd that her response no longer matters.
In the final scene, Syd arrives at 'Frame' and discovers that they have indeed used Lucy's photos taken of her in their latest magazine piece. As everyone in the office congragulates her for a job well done, the shaken Syd cannot handle this latest turn of events and leaves the office to take the rest of the day off.