The central plot of "20th Century Girl" is built on a crucial misunderstanding. Na Bo-ra spends the first half of the film observing Baek Hyun-jin for her friend Yeon-du, only to fall for his best friend, Poong Woon-ho. The first major twist occurs when Yeon-du returns from the U.S. and reveals that the boy she fell for was actually Woon-ho, who was wearing Hyun-jin's school jacket that day. This revelation throws Bo-ra into turmoil, forcing her to suppress her feelings for Woon-ho out of loyalty to her best friend.
After Yeon-du selflessly prioritizes their friendship, Bo-ra and Woon-ho are free to be together. They share a heartfelt confession at the train station just before Woon-ho moves back to New Zealand, promising to keep in touch. They exchange emails for a time, but Woon-ho suddenly and inexplicably goes silent, leaving Bo-ra heartbroken and confused for years, assuming he simply moved on.
The final, devastating twist is revealed in the film's present-day timeline (2019). The adult Bo-ra receives an invitation to an art exhibition. There, she meets Woon-ho's younger brother, Joseph, who informs her that Woon-ho died in an accident shortly after he stopped emailing her all those years ago. The film concludes with Bo-ra watching a final videotape Woon-ho made for her, where he confesses his love and his hope to see her in the 21st century. The title is a poignant reflection of the fact that their story, and Woon-ho's life, never made it past the 20th century.