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This movie starts out with Alfie (Jude Law) waking up in his bed. He speaks directly to the audience throughout the movie, so we get his first hand account of what's going on and how he feels (or what he wants us to think how he's feeling). He introduces himself and goes into his morning ritual. He is a self-proclaimed "fashion whore" and thinks that pink looks fabulous on him, and any man comfortable with his masculinity should be okay with wearing it. He puts on an expensive looking Prada suit, then lets us know that it was off the sales rack. We find out that Alfie is really only a chauffer, driving around wealthy individuals in limos. He says it's just a stepping stone considering he's going to open up a limo service of his own with his best friend.

We then get to meet Alfie's best friend, Marlon (Omar Epps). Marlon is visably upset and Alfie lets us know that he has just been dumped by his beautiful girlfriend, Lonette (Nia Long). Marlon cheated on her with his ex-girlfriend, then showed up drunk at her door at 3am throwing up. He can't understand why she won't take him back.

That night, Alfie meets up with one of his many women. Jane Krack-something (from Ally McBeal). They're going at it pretty hard, and when done, Alfie does the obligatory three seconds of cuddling before proclaiming that he has to go pick someone up and needs to go. He says Jane is just gorgeous and gives her his highest rating: an A -. On his way to drop her off, Alfie lets us know that ol' Jane is starting to get too attached and it's probably time to walk away. At about this time, she slips her red thong into his coat pocket. When he drops Jane off, we realize that this is the last time he's planning on seeing her.

Immediately afterwards, he goes to his "quasi-sometimes girlfriend" Marisa Tomei. She's a single mom who is obviously in love with Alfie. She has a little boy who's about five or six, and Alfie is absolutely in love with the little kid (this is where his softness starts to come out). Alfie reaches down into his pocket and sees that Jane's thong is still in his pocket, he puts it in Marisa's trash real quick before tucking her little boy in bed for the evening. A couple of days later, Alfie shows up at Marisa's door drunk looking to get some attention. She opens the door but keeps the chain on. Asking why she won't let him in, she throws the red thong in his face and tells him to leave.

He tries to act like this doesn't bother him, but it becomes more and more obvious throughout the movie that he genuinely cared for Marisa and her little boy. One night, Alfie goes out with Marlon to a bar that is owned by Lonette (his girlfriend that dumped him). After Marlin leaves, Alfie stays behind to convince Lonette to give Marlon a second chance. They start up a game of pool and start taking shots, before they know it, they're having sex on top of the pool table. Alfie decides the best thing to do is just forget about it.

He then starts trying to sleep around as much as he can but comes across a small problem: he's become impotent. He goes to the doctor where the doctor tells him it's most likely because of stress (due to breaking up with Marisa). While down there, the doctor finds a lump and they have to do a biopsy (we later find out it was benign). On his way home from the biopsy, he sees Lonette waiting at his apartment. She tells him that she's pregnant and it's most likely his. They go to the clinic so she can have an abortion. She has since gotten back together with Marlon, they're engaged, and she knows if the baby is born half white (Marlon and Lonette are black), she'll most likely lose Marlon. You see Alfie genuinely upset over the whole process. When Lonette finally exits the clinic, Alfie asks her how she is and all she can say is, "Empty". Soon after, Lonette and Marlon move to upstate New York and Alfie doesn't really see them anymore.

Christmas is soon approaching, and Alfie states that no one should ever be without a relationship during the holidays. At about this time he meets Nikki (Sienna Miller). She is this hippi-esque beautiful wild child who he falls for immediately. They start this passionate affair and he has a blast with her. At a party, he starts to realize she's sometimes not all the way with it. Apparently, she's on medication to control her mood swings. She is obviously in love with Alfie though, and Alfie genuinely feels for her. Regardless, he starts an affair with Susan Sarandon, who is a very wealthy woman with Alfie's personality. She's used to using men for sex and Alfie falls for her. Soon after, Alfie dumps Nikki and you truly feel for her when she's leaving with her suitcases in the rain.

Alfie decides to go over to Susan Sarandon's house but only finds out that she's there with a "younger man". He's heartbroken. Finally someone has done to him what he's done to so many. While driving down the road, he sees Marisa Tomei in a cafe and stops in to see her. She looks absolutely beautiful, and he asks if they can start dating. At about this time, her boyfriend comes in and sits next to her - pretty much answering Alfie's question.

Feeling his life spiraling downward, he decides to go see the two people that always meant the most to him: Lonette and Marlon. He borrows a car from his boss and makes the trek to upstate New York. Once there, Lonette comes outside to welcome him. She has a weird look on her face and just then, Alfie can hear a baby cry. He gets excited asking if Lonette and Marlon had another baby, and she says no. They go inside to see the baby and we realize that he's half white, meaning it's Alfie and Lonettes - she never had the abortion. He goes outside in shock, and that's when Marlon drives up. Marlon can't even look at him. Marlon stayed with Lonette because he loved her, but he was incredibly hurt by Alfie's betrayal. Alfie drives off but has to pull over because he breaks down.

He contacts an elderly man he met at the doctor's office that gave him some advice. They go for a walk on the beach where the elderly man puts it simply and eloquently, "Alfie, think before you unzip."

The end of the movie is Alfie on a pier looking over the water. We see a blonde walking and realize it's Jane from the very beginning of the movie. Alfie walks up to her and they start talking. She's visably uncomfortable considering he never called her back and dumped her with no explanation. He tries to explain why, saying he gets nervous when things start to get serious. She looks at him and says, "The only person you need to make an explanation to is yourself.", then walks off.

Alfie ends the film acknowledging that so many women had taken him into their lives, accepted him, treated him wonderfully and he always just left them. He says that he thought he was getting a good deal, but he's come to realize he got the short end of the stick. It ends with you not really knowing if he's going to change his ways or not considering the sly grin he gives the camera in the end. You can't help but like him though.