Alfie
Tags: melodrama, flashback

Plot synopsis:
Alfie (Jude Law) is a Cockney limo driver who regularly beds and discards beautiful women. In addition to maintaining a casual relationship with a single mother named Julie (Marisa Tomei) that he refers to as his "semi-regular-quasi-sort-of-girlfriend thing", he also sleeps with various girls on the side, such as the unhappily married Dorie (Jane Krakowski). At the first inkling Dorie wants something more than casual sex, he decides to block all contact.
Alfie wants to go into business with his coworker and best friend, Marlon (Omar Epps), but Marlon is preoccupied with trying to win back his ex-girlfriend, Lonette (Nia Long). Marlon asks Alfie to put in a good word with Lonette. Alfie meets with her at a bar to persuade her to get back together with Marlon - and ends up having sex with her on a pool table. Alfie meets with Marlon the next day, terrified that he knows about their indiscretion, but is relieved when Marlon says he and Lonette got back together.
Alfie goes to Julie's place for another booty call, but she throws him out after confronting him about his affair with Dorie, which she learned about after finding the other woman's panties in his laundry. Alfie soon gets another unpleasant surprise: Lonette is pregnant with his child. Without telling Marlon, they visit a clinic and arrange for her to have an abortion. Soon afterwards, Marlon and Lonette unexpectedly move upstate without even saying goodbye to Alfie.
Following repeated failures to achieve an erection with various women, he visits a doctor who tells him he is perfectly healthy, and that his impotence is due to stress. However, the doctor also locates a lump in Alfie's testicle that may be cancerous. Alfie immediately has a test run at the clinic and spends a few anxious days awaiting the results. During one of his trips to the hospital, Alfie meets a widower named Joe (Dick Latessa) in the clinic bathroom. Joe imparts some life advice to the depressed Alfie: "Find somebody to love, and live every day like it's your last". Soon afterwards, Alfie finds out he doesn't have cancer.
Believing he's been given a second chance, Alfie decides to "aim higher" in his love life. To that end, he picks up a beautiful but unstable young woman named Nikki (Sienna Miller), and they quickly embark on a passionate, turbulent relationship. They move in together, but Alfie finds it hard to put up with her mood swings, especially after she goes off her medication. He begins to distance himself from Nikki, and sets his sights on an older woman, Liz (Susan Sarandon), a sultry cosmetics mogul. Alfie becomes infatuated with her, but she wants to keep their relationship strictly sexual. Alfie then breaks up with Nikki.
Alfie runs into Julie in a coffee shop, and finds that he still has feelings for her; to his dismay, however, she's now happily involved with someone else. A trip upstate to visit Marlon and his now-wife, Lonette, reveals that she never actually went through with the abortion. Alfie also learns that Marlon knows that Alfie got her pregnant, but nonetheless raises the child as his own. Marlon then cuts all ties with him. Alfie calls Joe, who tells him that he needs to get his life together. Alfie turns to Liz for comfort, but is crushed to discover that she has a new man in her life. Alfie demands to know what her new boyfriend has that he doesn't; Liz replies, "he's younger than you".
Alfie has a chance meeting with Dorie late one night. He tries to get back into her life, but she says that she wants no part of him. The film ends with Alfie talking to the audience about changing his ways.