New York, I Love You
(2008)

There are 10 main stories in the film, though throughout the course of the movie, many of the characters from various stories meet each other and interact.

  1. Two thieves (one professional, one recreational) play a game of one-upmanship.  Ben (Hayden Christensen) returns the ring he stole from Garry (Andy Garcia), who has yet to leave his wife for his student Molly (Rachel Bilson).  As he leaves, Molly catches up with Ben and they start to spend time with each other.
  2. A jeweler and his customer (Natalie Portman) discuss their respective religions; he is a Jain, she is a Hassidic Jew.  That night, she at her wedding and he driving home, they both smile at the idea of being able to marry.
  3. A composer (Orlando Bloom) spends his days reading Russian novels at the behest of his film's eccentric Director and having phone conversations with the Director's PA (Christina Ricci), who he has never seen.  She offers to read the books for him and fill him in so he can focus on scoring.  He opens the door to his apartment and finds her there and they finally meet.
  4. A writer (Ethan Hawke) persistently, and explicitly, hits on the woman who bums a cigarette off him.  She turns out to be a hooker and gives him her card. On that same street corner, Alex (Chris Cooper) and Anna (Robin Wright Penn) meet over a cigarette, and have a sexually-charged discussion about anonymous sex.  Anna leaves, saying she has to return to her husband.  She goes back to the restaurant, and sits down with…Alex and they finish their dinner.
  5. A teenage boy is stood up by his prom date and his sympathetic pharmacist (James Caan) sets up him last minute with his daughter (Olivia Thirlby), who it turns out is in a wheelchair.  When they run into his ex (Blake Lively), she lies and tells the ex that the boy is taking her because of the Make A Wish Foundation.  They have sex in Central Park, fulfilling his wish for prom night.  When he drops her back at her home, she steps out of her wheelchair - turns out she's a method actress and studying being wheelchair bound.
  6. Gus (Bradley Cooper) and Lyrida (Drea de Matteo) had a one-night stand and both were more affected by it than they expected.  They plan to meet up for a second night, but begin to doubt themselves and their connection.  When they finally meet up though, their second-guessing is forgotten and they take a cab home.
  7. A retired opera singer (Julie Christie) checks into a hotel, planning to commit suicide.  She is befriended by a melancholy Russian bellboy (Shia LaBeouf).  He interrupts her as she is planning to jump, and when he goes to close the window, falls to his death.  The hotel manager (John Hurt) looks out the balcony where the body should be and tells her there is nothing there.  She asks him to close the window.
  8. A dancer spends the day in the park with his daughter before handing her over to his ex-wife and her new partner.    He tells her their daughter misses her, she asks him to take the daughter again the next day, and he agrees.
  9. A painter keeps painting the portrait of a young shop girl.  He eventually asks her if she would sit for him, but she says no.  Later that day she sneaks out from her job to go see him, but he has died. As she leaves his apartment, she finds one of the paintings he did of her and takes it home.
  10. Abe (Eli Wallach) and Mitzie (Cloris Leachman) celebrate their 63rd wedding anniversary, talking a walk at a slower pace than the city around them.

Throughout the film a woman keeps running into the various characters, always filming on a video camera.  We see at the end that she is a video artist; she displays her footage at an art show and we see glimpses from all the stories in the film.

Thanks Mary C!