Opening in the year 2046, in which a man named Tak (Takuya Kimura) attempts to persuades wjw 1967 (Faye Wong) to travel back in time with him, the film soon shifts to the year 1966, in which Chow Mo-wan (Tony Leung Chiu-wai), a struggling author, asks the woman he loves, Su Lizhen (Gong Li) to sail with him from Singapore to Hong Kong on Christmas Eve. She declines, and over the next three years, we return to Chow Mo-wan on December 24 as he finds himself with another woman each year -- lighthearted Lulu (Carina Lau) in 1967, eccentric hotel heiress Wang Jingwen (Faye Wong) in 1968, and Bai Ling (Zhang Ziyi), a high-class prostitute, in 1969. In time, Chow Mo-wan and Wang Jingwen become reacquainted, and a love affair blooms, but the fates are not on their side.