Matt Simon, Josh Hartnett, a young advertising executive, returns to Chicago with his fiancée Rebecca after spending the last two years in New York. On the way to a restaurant for a meeting that would kick off a business trip to China, he bumps into his old friend Luke, Matthew Lillard, who is preparing for his own venture. Inside, Matt believes he overhears Lisa, the beautiful dancer he loved two years earlier, who vanished overnight. The moment tugs at him with a mix of hope and doubt, and he finds himself torn between the present and a past that refuses to stay buried.
Unable to face the possibility that the woman in the crowd could be Lisa, he cancels the trip and launches an obsessive search for her, a pursuit that unfolds alongside flashbacks of Matt and Lisa’s romance. A key card left at the restaurant points him toward a hotel, where he discovers Lisa’s silver compact and a clipped newspaper article. He leaves a note for Lisa at the restaurant bar, borrows Luke’s car, and tails the man from the article to an apartment. There, Matt finds a note to Lisa under the door, with her key enclosed. The apartment is deserted, but he leaves Lisa a note of his own, asking her to meet him in Wicker Park, and he keeps the key as a tangible link to what might have been.
An ecstatic Matt returns the car to Luke, who is furious because he has missed a date with his new girlfriend Alex. When Alex calls, Matt takes the blame and Luke is mollified, though the tension between past loyalties and present commitments lingers. The next day, after waiting in vain at Wicker Park, Matt goes back to the apartment and is confronted by a woman who is also named Lisa. She says the apartment is hers, but she has a coat and red-soled shoes with a broken heel identical to Lisa’s—shoes that came from Luke’s shop, where Lisa first met Matt. She claims she was at the hotel because the man in the newspaper was stalking her, and asks Matt to stay the night. They end up sleeping together. But the truth surfaces in a cascade of revelations: this “Lisa” is actually Alex, Lisa’s old neighbor and friend. Alex had fallen in love with Matt from afar, but he had met and fallen for Lisa before Alex found the courage to speak to him. The man from the newspaper was stalking Lisa, and Alex had agreed to swap apartments with her for a few days before Lisa left for a new job in London.
Luke persuades Matt to come with him that night to see Alex perform in Twelfth Night. She is unrecognizable in stage makeup, but panics after she sees Matt in the audience with Luke. Matt returns to the apartment, still sensing Lisa’s presence despite its emptiness, and spends the night. Alex sleeps with Luke that night. In the morning, when Matt calls Luke, she answers the phone then drops it in a panic. She overhears Luke say Matt is at the apartment, and runs out to call him and meet him there. After receiving Matt’s note at the restaurant, the real Lisa calls and asks Luke to tell Matt to meet her at three o’clock, saying he will know where. When Alex arrives at the apartment, Matt gives her another pair of red-soled shoes, Lisa’s size, but they are too big. She realizes he suspects something, but Matt says he can exchange them and leaves. Alex then calls Luke and asks him to meet her at the restaurant.
Now suspicious, Matt follows Lisa (Alex), bumps into Luke, and follows him into the restaurant to finally meet Alex, the girl Luke is in love with. Matt confronts Alex, and her deception is revealed. A flashback reveals that two years ago, the same day Matt asked Lisa to move in with him, Lisa was offered a last-minute job touring with a show in Europe and had to jump on a plane. Lisa had given Alex a note to deliver to Matt, telling him she loved him and wanted to live with him. Instead, Alex had kept the note, deleted all the messages Lisa had left for Matt on his answering machine, and told Lisa that she had caught Matt in bed with another woman. Matt never learned why Lisa left, seemingly without a word.
In the present, a confused Luke tells Matt that Lisa called and wants him to meet her at three o’clock before she returns to London. Matt is unsure where to meet, but Alex gives him Lisa’s old note and he realizes that Lisa is at Wicker Park. Arriving too late, Matt races to the airport, where he is met by Rebecca, who has come to pick him up from the business trip to China he never went on. Lisa is nearby on the phone, listening to Alex admit what she has done and apologize. Matt spots Lisa in the crowd, and, moved, follows her toward a reunion that is finally theirs, as Lisa senses his presence and turns to kiss him. They are reunited at last, the past resolved and their connection renewed.
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