Ip Man's peaceful life in Foshan changes after Gong Yutian seeks an heir for his family in Southern China. Ip Man then meets Gong Er who challenges him for the sake of regaining her family's honor. After the Second Sino-Japanese War, Ip Man moves to Hong Kong and struggles to provide for his family. In the mean time, Gong Er chooses the path of vengeance after her father was killed by Ma San.

Faced with the task of creating a film about first love for his producer Wong Kar-wai, Kot ruminates on his creative process, his rejected ideas, and finally his two chosen tales, about a sleepwalker guided through the night by a lonely admirer, and a married convenience store owner faced with the vengeful first love that he once rejected.