The film tells the story of a male college student, Gyeon-woo (Cha Tae-Hyun), and the Girl (Jun Ji-hyun) who is never named in the movie. Gyeon-woo just cannot seem to catch a romantic break. His prospects are so pathetic that even his mother tries to help, telling him to visit his aunt for two reasons. Firstly, because Gyeon-woo reminds his aunt of her son who drowned recently; secondly, because there is a girl his aunt wants to introduce him to. Gyeon-woo repeatedly puts off going to see his aunt.
The movie begins with Gyeon-woo on top of a mountain, speaking wistfully about a girl he knew two years ago that had buried a time capsule with him on that mountain. She had never returned like she'd promised. Next, one sees Gyeon-woo at a photo studio, having his passport photo taken. He is called by his aunt so that she can finally introduce him to the girl she's been trying to set him up with. The movie then flashes back to the past.
While Gyeon-woo is at a restaurant with some of his friends, he is interrupted by a call from his mother telling him to go meet the girl that his aunt wants to set him up with. He refuses and continues to eat with his friends. At the train station on his way to his aunt's, he observes a girl, drunk, standing precariously close to the edge of the train platform as the train approaches; he pulls her to safety just in time. Inside the train, Gyeon-woo cannot help but stare at the girl wavering back and forth. He is slightly attracted to her but repulsed by her drunkenness. Finally, she throws up on a passenger and faints but not before she calls Gyeon-woo "honey". The passenger aggressively chides Gyeon-woo and tells him to take care of his girlfriend. Gyeon-woo, completely flustered, carries her all the way to the nearest hotel. While he is showering, her cell phone rings. Stark naked, he runs out to answer it and informs the caller of their location. Just as Gyeon-woo realizes there are no towels in the shower, a pair of women police officers burst into the room and arrest him.
After getting out of jail—where he was bullied by gangsters—he goes home. His mother beats him with a vacuum cleaner for not turning up at his aunt's and there is a brief flashback of his lifetime failings as a student. He receives a call from the Girl demanding he meet her and explain why he was naked in bed with her. The Girl's dominating and demanding tone during the telephone call establishes her typical posture as a xanthippe, an attitude she maintains throughout the film. Both at the takeaway joint and at the bar to which she drags him she tells him to order, criticises his choices and then tells him what to order. Over soju she cries, admits to breaking up with her boyfriend the day before and gets thoroughly drunk, resulting in another trip to the previous hotel.
After this second overnight stay at the hotel, she begins to become a more active part of his life. She visits Gyeon-woo in school and manages to get him to hang out with her. In one situation she obtains permission from a teacher by claiming she needs him to accompany her on the way to an abortion, with Gyeon-woo being the father. Her mood swings wildly from joyful to downright violent but Gyeon-woo puts up with it and lets her abuse him for her amusement.
She is an aspiring scriptwriter and throughout the movie gives Gyeon-woo three different screenplays from different genres. The first is an action movie—The Demolition Terminator—which switches gender roles, symbolically having the Girl save her helpless lover (Gyeon-woo). The second is a wild perversion of a Korean short story—Sonagi—in which the Girl, having died, asks that her lover be buried along with her—even though he's still alive. The resulting situation is quite humorous. The last is a wuxia/samurai movie spoof full of genre clichés and anachronisms. All three feature the same common thread: the Girl is from the future.
Despite all the horrible things Gyeon-woo endures, he is determined to help cure the girl's pain. In one scene, he decides to surprise her for her birthday and takes her on a nighttime trip to an amusement park which ends up quite differently than how he planned: The pair encounter an AWOL soldier who holds them hostage and rants about his misery. Gyeon-woo convinces him to release her, and she in turn convinces the soldier to free Gyeon-woo and go on with his life. Throughout the first half of the movie she is resolute in her pain, dishing it out in plenty. As the second half comes around, however, she begins to change: she shows vulnerability.
The second - more dramatic - half of the movie begins with the Girl waiting for Gyeon-woo after class. They are walking through the university campus when she suddenly complains about the pain caused by her high-heels and convinces Gyeon-woo to switch shoes with her. Overjoyed, she tells him to chase her, which he does wearing her high heels. It starts raining and they return to her home. At her house Gyeon-woo overhears an impassioned argument between the girl and her mother over her relationship with him. He does not hear from her for quite some time and his life without her begins.
However, one day she calls him and tells him to bring her a rose during class to commemorate their 100th-day anniversary. He does this, leading to a touching and romantic scene where he arrives in disguise and is about to leave the packed auditorium but is led to the front by the beautiful melody of George Winston's variations on Pachelbel's Canon in D. The Girl is onstage playing a piano in front of an audience of her all-female classmates who applaud in approval at his romantic gesture - a similar gesture, the viewer is later informed, was performed by her previous boyfriend. As the night further unfolds he is confronted at her house by her parents. Her father is naturally infuriated that she is drunk again and demands a break-up.
Time passes and one day the Girl calls Gyeon-woo to meet her for dinner. When he arrives he is surprised to see her with a date. The Girl introduces Gyeon-woo to him as "her friend." During dinner, the Girl leaves the table briefly, leaving Gyeon-woo and her date by themselves. Gyeon-woo candidly offers advice on how to ensure her happiness by following ten rules. He devised his rules from considerable pain, dedication and devotion to the Girl. When she returns her date begins to explain the rules. It is at this point that she realizes just how well Gyeon-woo understands and cares for her. She abruptly leaves her date and searches for Gyeon-woo. Once reunited the two realise they are at a turning point in their relationship.
They travel to a mountain in the countryside where she unveils a time capsule. During the previous night the couple wrote their true feelings in letters which the Girl says will be buried next to a particular tree on the mountain. They agree to meet again at the tree after two years to read the letters together. After burying the time capsule they go their separate ways.
During the two year span, Gyeon-woo works hard to improve himself in many ways, even writing My Sassy Girl which someone has bought the movie rights to, an event he eagerly anticipates telling the Girl about. When the agreed upon date arrives, he travels to the mountain but the Girl does not show up. Eventually, he opens the time capsule and reads her letter and learns the root of her angst and behavior: Gyeon-woo reminds her of her previous boyfriend who, rather than breaking up with her, actually died before she met Gyeon-woo. All through the time the Girl and Gyeon-woo were seeing each other she had been seeing her dead boyfriend's mother, who wants to introduce her to a nice young man.
A year after Gyeon-woo visits the tree, the Girl finally arrives. Sitting under the tree is an old man. During their conversation the old man reveals the secret of the tree, that it is not the same tree; the original tree had been struck and killed by lightning a year before and a similar tree had been planted by a young man so that someone special wasn't sad, and that he has read the letters. The Girl says she had hoped that destiny would bring the couple together during the two years. As the girl begins to read the letter, she sees a UFO (time machine) flying away. This lead her to believe that the old man was Gyeon-woo from the future.The Girl then tries to call Gyeon-woo repeatedly, but she was informed that number is either changed or doesn't exists.
The film then cuts to Gyeon-woo entering a subway station, wearing the same suit he was wearing at the beginning of the movie. The flashback has ended and continuity is resumed from right after Gyeon-woo leaves the photo-studio. Gyeon-woo is caught outside the shutting doors of a train, presumably ignorant at first of the Girl's presence on the train but after a few seconds of staring he seems to realise whom it is he sees from behind. As the train pulls out he runs along but has to give up.
At lunch with her deceased boyfriend's mother after a year-and-a-half, the Girl is surprised to hear a familiar voice apologise for his lateness. The mother introduces her nephew Gyeon-woo whom she has been trying to introduce to the Girl for years. The mother, who is Gyeon-woo's aunt, tells the Girl to go out with him, he'll make things easier for her and then tells Gyeon-woo that the Girl can give advice to him about his impending trip to England but Gyeon-woo replies, "I don't have to go now." The pair hold hands under the table and the Girl says she thinks she met a man from the future (Gyeon-woo's future self). The final shot shows the pair in their activity from earlier in the film, dressed in school uniforms going into a bar.
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