Plot
The plot is set in New York City over three days in the lives of 10 different characters who interact with each other in various sexual encounters, which follow from one character to the next.
It begins when a young woman named Julie (Condola Rashad) meets at a loft with her former anthropology professor, Adam (Justin Kirk), where she tells him that she is a virgin and wants him to take her virginity.
Afterward, the plot shifts to Adam, who visits a tarot reader named Erika (Jennifer Tilly) for advice on his sexual prowess and superstitions. She performs a ritual on him to "cleanse" Adam of his sexual needs.
Erika then meets with Diego (Jason Day), a much younger bicycle messenger whom she meets for weekly sexual trysts in a Harlem apartment, where Diego confides in her that he is in love with another woman. Erika gives him advice on how to court her.
Diego then goes to the house of Laura (Paz de la Huerta), the woman he has a fixation on, where she invites him in but tells him that she cannot have sex, for she has a bad heart and had surgery where she carries a large scar on her chest. Diego tells her to accept her physical deformity as it is to feel accepted.
Laura then goes to her chiropractor, named Matt (Lee Pace), where she dresses up in revealing underwear and tries to seduce him. He first refuses her advances but eventually gives in to them.
The next day, Matt visits Kim (Vahina Giocante), a young French woman he is dating, who reveals to him all about her own sexually active life with other men and women and her comfort with it.
Kim works as a switchboard operator in a local answering service, where a regular caller named Julian (Thomas Sadoski) wants to meet with her for lunch the following day. Unsure of the man he is, Kim has her girlfriend meet with him at a local cafe. She becomes uncomfortable with the way Julian hits it off with the other woman, so she reveals herself. Julian understands Kim is unsure, and they spend the night together in a threesome with Kim's girlfriend.
Julian is revealed to be a speechwriter who visits a call girl named Alice (Ingeborga Dapkunaite) on a weekly basis, where she practices bondage acts on him. Alice tells Julien that she is considering giving up her call girl profession to open her own art gallery and cannot see him anymore. Julian tries to persuade Alice not to give up on what she does best, but her mind is made up, and she walks out to spend alone time in her new artist studio.
Alice goes to a health spa, where she meets and has a sexual encounter with a younger man named Shawn (Ben Levin) in the steam room. Shawn is rushed to the hospital after he slips and hits his head and cannot remember the sexual encounter due to short-term memory loss. Alice accompanies him to the hospital to tell Shawn that their encounter did happen.
After Shawn leaves the hospital, the events come full circle when he meets with his childhood friend, who happens to be Julie. He first tells Julie that he wants to have sex with her, and Julie disapproves, claiming it would be weird since they are best friends. The next day, they meet up, and Julie decides she wants to try having sex and assumes Shawn is a virgin; he protests and says her reasons yesterday were valid and he is not a virgin, but she does not believe it and convinces him to have sex on the rooftop. The final scene is of Julie breaking the red bracelet she shared with her anthropology professor and holding hands with Shawn while he reads a book.
