Set in New York City spanning six or seven months, Greg (Daniel Carlisle) has just moved in with his girlfriend Molly (Emily Peck) who lives in the city. During their first night out since moving in together, Greg and Molly go out for drinks and a meal at the local Four-Faced Liar bar where they meet Trip (Todd Kubrak), his girlfriend Chloe (Liz Osborn) and his lesbian friend Bridget (Marja Lewis Ryan). Molly and Bridget bond as they discuss Wuthering Heights and relationships. Molly tells Bridget that she has everything in common with her boyfriend, but Greg lacks passion. Bridget tells Molly that she doesn't have a girlfriend because no one can hold her interest for long enough to bother. Bridget in fact lives with Trip and Chloe in the spare bedroom where she always gets up at the same time every morning as Trip and they both brush their teeth together while standing in front of the bathroom mirror.
Trip and Greg bond over drinking beers and smoking joints on the roof of Trip's apartment building. Trip soon shows concern with Greg over Molly spending more and more time with Bridget and he reminds Trip that Bridget is a lesbian. Greg tells Trip that he is getting worked up for nothing.
One evening around Halloween, Trip annoys Chloe by blowing off a ballet performance to watch sports. She takes Bridget in Trip's place to watch the show. However, Trip wins her back with a candlelit apology, her favorite dessert, and a self-deprecating dance. That same night, Greg drunkenly tries to force an unintrested Molly into sex. She leaves him to stay with Bridget until he apologizes.
At a New Years Eve party at the bar, Molly laments to Bridget that she has never been thrown up against a wall and kissed. In the restroom, Bridget does just that whens she follows Molly in, and the pair has breathless sex in the years final moments. Afterwords, both Molly and Bridget appear shocked by their own actions. Molly returns to Greg, but she begins a secret affair with Bridget. A montage is shown over the next few weeks as Molly's bond with Bridget grows stronger as they walk arm-in-arm or hand-in-hand along the street as well as make out with each other in private and in public; from Bridget's bed, to sofa, to at a park, on the street, and in a concrete underpass.
One day, Chloe catches Trip having sex with a random girl and she finally leaves him. When she enters Bridget's room to gather some stuff and finds a very naked Molly in bed with her after another night of lovemaking, Chloe openly expresses her disapproval and disappointment with Molly and her infidelity.
When Trip also finds out about Molly and Bridget, he reports it to Greg, who forgives his girlfriend because "she's worth it". Molly then breaks off her romantic relationship with Bridget and announces that she is marrying Greg.
A few days later at Molly's birthday party at the bar, Trip attempts to woo Chloe back, while Bridget shows up and presents her case to Molly with a simple, I like you. Greg sees Bridget outside the bar and he confronts her outside by asking if she loves Molly. The angry and jealous Greg finally looses his temper and throws Bridget up against a car over her presence at the party. When Chloe and Molly realize that both Greg and Bridget are missing, they all run outside where Trip pulls Greg off of Bridget who wonders off while Chloe follows and tries to comfort her.
As the film comes to an end, Molly ends her engagement with Greg who moves out and back to his home town. Molly then visits Bridget to report Greg leaving her and both women lie in bed side by side, staring at the ceiling. Bridget tells Molly that she's totally keeping her interested and that she's trying to be the one Molly wants. Then she questions the look on Molly's face, to which Molly responds with the look indicates love. Bridget cries a little of not able to say anything back. The final shot shows both of them continuing to stare at the ceiling, each speculating their next move.
However, their facial expressions tell more than words ever will. Bridget's expression is one of entering unexplored territory (i.e., that of love). Molly's expression is one of self-doubting as she has fully committed to living a full-on lesbian life very different from that she has ever experienced.