Captures a generational moment - young people on the cusp of truly growing up, tiring of their reflexive cynicism, each in their own ways struggling to connect and define what it means to love and be loved.
Six New Yorkers juggle love, friendship, and the keenly challenging specter of adulthood. Sam Wexler is a struggling writer who's having a particularly bad day. When a young boy gets separated from his family on the subway, Sam makes the questionable decision to bring the child back to his apartment and thus begins a rewarding, yet complicated, friendship. Sam's life revolves around his friends-Annie, whose self-image keeps her from commitment; Charlie and Mary Catherine, a couple whose possible move to Los Angeles tests their relationship; and Mississippi, a cabaret singer who catches Sam's eye.
- Sam, a struggling writer is asleep in bed with an unknown (presumably)female who dresses quickly, trying to leave before Sam wakes, rushing out as the phone starts to ring. Sam wakes to Annie, a friend with alopecia areata (an autoimmune disorder that has made her lose all her hair) calling to remind him about a party she is hosting, and telling him which clothes to wear. Sam, during the message quickly preps for a meeting, calls Annie from his celular phone to tell her he messed up, slept late and ruined his life. She assures him he will be fine. He promises to be early to her party.
Enroute to his meeting, Sam, realizes a boy is separated from his family & tries to take him to the police, where the boy resists. Sam, not knowing what to do, takes the boy (who will not talk, not even to answer basic questions) to his meeting, asks the receptionist to watch after the boy, & during the meeting (about a novel sam has written) sees the boy running the halls. Sam interrupts the meeting to grab the boy and sit him on the couch in the in the office with sam, which promptly terminates the interview. As Sam and the boy is leaving the secretary says bye to "Rasheen", the boy.
On the way home Rasheen says he is thirsty, and Sam uses this as an excuse to enter a bar where a red head he is interested in works. Sam uses the opportunity, and Rasheen, as an excuse to break the ice with the girl (Mississippi, from Mississippi).
When sam cannot get any information from Rasheen, he goes to Annie's party with the boy and meets with his cousin, Mary Catherine, who's boyfriend, Charlie is in Los Angeles on business. During the party, Annie reveals her disorder as Mary gets a call from Charlie, where it is revealed that Charlie loves Los Angeles and it is suggested that Mary hates it.
Sam ends up going to see Mississippi at the bar while Rasheen sleeps on his couch, learns that Mississippi is a singer and refuses to go see her in case she is not a good singer, because he readily admits he likes her and thinks she is great. Sam invites her home and convinces her to live with him for 3 days, which he regrets the next morning. Annie is having trouble with a colleague (Sam number 2) who works on 7th floor but continually visits the 5th floor and takes pictures of Annie. Sam takes Rasheen to Social services and leaves him there, asking Rasheen not to mention his name, but later finds Rasheen following him as he gets home.
Mary and Charlie have conversations about Los Angeles versus New York, and it is revealed that Mary is afraid to leave new york. During the movie we also see evidence of Mary being pregnant (morning sickness) and she offers to break it off when Charlie proposes to her.
Mississippi finds out the truth about Rasheen and tries to break it off with Sam but he manages to momentarily salvage the relationship. Annie ends up sleeping with her ex, then finding out that he is "seeing" someone else. Mary goes to the doctor and finds out she's pregnant. Annie finds pictures on her desk and agrees to dinner with Sam number 2 and ends up dating him a while.
Sam (#1) goes to social services to find out about how to foster Rasheen, but gives too much information and leaves in a hurry (setting the stage for his arrest later). Mary tells Charlie to leave, but he coaxed out the truth, that she's pregnant, and they agree to live wherever, and become happy. Annie tries to break it off with Sam (#2) but he convinces her that she is worthy of love and adoration and they end up sleeping together. Sam (#1) gets arrested and released, with Rasheen getting sent to a different foster home, causing him to miss a performance by Mississippi, which causes her to break it off with him, telling him he is great writing short stories because he prefers to live short stories, while she is ready for the novel. Sam (#1) later gets a call from Annie , who gives him some of his own advice, causing him to go buy art supplies for Rasheen, who has been drawing great pictures during the events of the movie, and deliver them to Rasheen at his new foster home, and then goes to see Mississippi at a performance, where it is implied that they get back together and it is implied that everyone lives happily ever after.