NOTE: This spoiler was sent in by lorencastwho says... "This was a good movie; A little confusing at times to follow but in the end, very good."
We start off with seeing Matthew (Josh Hartnett) looking in a window at engagement rings and then goes inside and is talking to the jeweler. They dont show him purchase one, he seems to have trouble picking one out. Next he is in his office, he works in this very upscale office I think working in some kind of advertising.
He is headed off with this boss to a meeting at Bellucci's Restaurant to meet with 2 representatives from a Chinese company and runs into his friend Luke (Matthew Lillard). They talk a little bit on the street of how they havent seen each other for 2 years and Luke learns he is back in Chicago after moving to New York 2 years ago. Luke gives him his card of a Chinese shoe store where he works or owns they never really said and tells him to call him. As they are talking a woman meets him who we find out is both his bosses Sister and Matthew's girlfriend (Jessica Pare) I cant remember her name, she hands him a bottle of pills to take on the plane trip to China. While they are toasting, one of the Chinese rep's Toast "Heres to a long and happy marriage".... "Of their two Companies". This freaks Matthew out a little bit hearing the word marriage and he excuses himself to the restroom.
He walks back to the phone room and knocks on the door, we can barely see a shadow of what looks like a blond in the room and she tells him to hold on. He goes in to the restroom and takes one of the pills and through a vent can hear this woman talking and realizes it sounds like someone. This is where he starts to flash back to his ex Lisa (Diane Krueger). We see that he used to work in a TV & Video repair shop near Wicker Park and his co worker was working on a video camcorder that is playing on the screens when he sees Lisa on the screen and is taken away with her beauty.
Next we cut to him working in the shop one day and as he is working on another camcorder it is catching images from outside the window and he sees her (Lisa) on the screen. He jumps up and runs out knocking a girl down (Rose Byrne) into a video tape display. Important Later!! He follows Lisa to a modern dance studio where she is rehearsing. Now we cut back to present day in the restaurant where he runs out of the bathroom after who he thinks is Lisa and we see the back of somone run in to the people he was meeting with and break her heel and then run out. He never sees her face or hair because once he sees his girlfriend, boss and clients he hides around the corner. He then goes in to the phone room and just kind of stands there taking in the air of the woman's perfume and finds a newspaper folded up by the phone when he picks it up he finds a folder from the Drake Hotel with a card key and a room number written on it.
He is leaving the restaurant with his girlfriend where she drops him off at the airport to go to China. Once she gets in the car, he hides and waits till the car drives away before he takes off. He heads over to the Drake Hotel and to the room and knocks where no one answers. He uses the key he found to enter and finds a light on in the bathroom where he enters and finds a silver compact sitting on the counter. Next he walks over to the bed and sits and starts to act sleepy, he flashes back to the pills his girlfriend gave him to sleep and how he took one in the restroom of the restaurant. He then falls back and sleeps.
We then are taken to another flashback where he walks in the Chinese Shoe Store and walks up to his friend Luke who is helping woman with trying on shoes. He tells Luke how he saw this girl and thinks he's in love but he doesnt know who she is or her name. While they are talking Luke points out what a beauty a girl (Lisa) is in the window. Matt tells him thats the girl, She then walks in to the store and Matt runs to the back room. He tells Luke he has to talk to her and to give him some shoes. He then walks out and acts like a store clerk asking if he can help her? She inquires about some black shoes with a red heel that are in the window. Important Later!! He goes to get her an 8.5 size and she tries them on and somehow they dont fit right. He offers to special order her another pair and call her when they come in if she gives him her phone number. They have some banter which i didnt quite catch about Modern Dance and she seems to remember him from the studio watching her earlier. He asks her out and she turns him down. Then she writes on the box something and tells him to call her when the shoes arrive. Once she leaves he looks down and sees that shes written a meeting place for tomorrow at some cafe. We next cut to them at the Cafe talking and walking in the park and him describing how he loves taking pictures because ordinary things can be soo beautiful. Next he is driving her home and she gets out and he starts to drive off and then backs up and runs up to her apartment and knocks and he rushes in to her arms and they make love. We then see a flash off them later in an apartment dancing around and in love. Next he shows up at her dance studio and asks if he can talk to her. She mentions shes about to go into rehearsal and he says its important so they go to a bar and are sititng when he mentions he was offered a job in New York working for an ad agency who likes his pictures. He tells her how she is it for him and he wants to build his life with her and he wants her to move in with him. She says she has to go and to meet him in Wicker Park at 3pm tomorrow. We cut to him in Wicker Park and waiting around and then he heads home dissapointed and checks him machine and there are no messages. Next he goes to her dance studio and a guy tells him she left with some European dance show that wanted her right away.
He then wakes up in the bed at the Hotel and finds a Article torn up in the ashtray of someone who has died.
He goes to the shoe store with Luke and tells him everything about thinking he found Lisa. He asks to borrow Lukes car to go to the funeral hoping he will run in to Lisa. Luke tells him okay but he has to be back by 7pm because he has a date. He goes to the funeral and theres only one man left and follows him to an apartment where the man leaves a envelope and a rose at the door. Once the man leaves he gets the envelope and its addresses to a Lisa with a note beggin her to call him and a key. He takes out the note and writes a note of his own that tells Lisa he has her key and to meet him in the park at 3pm tomorrow and that he must talk to her.
He is later in the park waiting and waiting and no one shows. He then goes to Belluccis Restaurant and leaves the hotel key and leaves a note for Lisa saying he's been trying to find her and to call him at Luke's apartment. He goes back to the apartment, knocks and enters the apartment where he sees the black shoes with the red heel and the one heel that was broken in the restaurant. While he is looking around someone comes in and we see someone walking around and wearing a jacket similar to the one Lisa was wearing in Matthew's flashbacks. She is looking out the window when Matthew comes up to her and says her name. We see that it is Rose Byrne and she is freaked out by him being there and tries to hit him, he says its okay he is Lisa's friend and she says thats funny because she is Lisa. They talk and he finds out is was her in the restaurant and its her apartment and the guy that came and left the rose is a infatuated lover. Matthew starts to leave and she asks him to stay awhile because she is scared of the guy coming back. Oddly enough he agrees to sleep on the couch and while asleep he finds her watching him and then takes off her robe and is naked and they wake up in bed together.
She wakes up and starts to leave saying she is a nurse and has a shift but asks him to wait for her. We then see her heading to her car and sitting in it. She then has a flash back of meeting Lisa where they lived across from each other and them becoming friends and confiding in Lisa that she is in love with a guy but she doesnt really know him and one day when their walking she goes in to Tv & Video store to pickup her camera and we see this is when he ran in to her and she fell in to the video tapes and she sees him go after Lisa on the street. She is upset because she loved him even though she never approached him and visibly jealous of him going for Lisa. Next a car honks and she is shaken back to reality and drives away in her car to an apartment where Lisa is. We learn Rose Byrne name is really Alex and that is her apartment where Lisa is and that Lisa was afraid of the guy so she is staying with Alex and the apartment that Matthew went to was really Lisa's apartment and the hotel room was where she stayed until the guy found her there.
Next we see Luke meeting up with his date who is rehearsing at a Theatre and is an actor. We cut to the woman who is taken off her heavy makeup and see that it is Alex. They are going to go out and he starts talking about Matthew and how he thought he found Lisa but it landed up being some Psycho girl. She becomes upset knowing its her hes referring to and says she doesnt feel well and has to go.
Lisa looking for her compact goes to Belluci's and asks if she left it. The waiter says no but asks if her name is Lisa and hands her the envelope with the letter from Matthew. She calls Lukes apartment and asks for Matthew where he tells him hes not there but is on the way. Alex walks in after just having spent the night with Luke and he of course tells her this.
Next we see Matthew back at Lisa's Apartment having remembered the black shoes with the red heel that were broken he gets another pair for Alex whos name he still thinks is Lisa and when he goes to try them on her they are too big because she wears a 7 and the real Lisa wears an 8.5 which is the size of the broken shoes. He now knows shes lying about something so he follows her to Belluccis where she is meeting Luke, Luke sees Matthew and invites him to meet his girlfriend Alex. They walk up to the table and Matthew doesnt let on to Luke that he knows Alex. Alex and Matthew banter back and forth about love and he takes off to the park to meet Lisa after Luke tells him about the call. He in like sooo many movies is stuck in traffic and cant get a cab and just misses her. Luckily she told Luke that she had a flight to London to catch. Matthew races over to the airport searching in crowds when his girlfriend (Jessica Pare) walks up believing he just flew in from China. He quickly tells her he cant be with her and spots the back of Lisa's head in line to board the flight. Suddenly Lisa gets a call from Alex and she confesses shes been keeping them apart. We flashback to when Lisa was leaving to London 2 yrs ago she gave Alex a letter to give to Matthew, Alex at first rejects since her and Matthew have never met and then she gives Alex, Matthews apartment key to leave it on his bed. We see Alex enter Matthew's apartment and delete 9 messages Lisa left for him trying to explain her abrupt departure due to a show in Europe. Later we see Alex at her apartment talking to Lisa and telling her that she found Matthew in bed with a woman when she went to deliver the letter.
Back to present day, Lisa is sitting on the floor of the airport talking to Alex, hurt she hangs up with Alex and Matthew sees her sitting there and he comes up from behind and Lisa turns around and they embrace.