The famous cross-dressing Cantonese opera singer Chan Kam Foong passes away, leaving her secret journal to her granddaughter, Xiu Yin, an archival officer at the Singapore National Archives.

Xiu Yin reads through the journal that chronicles her grandmother's relationship with Dearest Intimate in their village in China to their respective escapes to the Nanyang before WWII and her desperate search for Dearest Intimate in Singapore. Her grandmother's reflections and letters to Dearest Intimate forces Xiu Yin to examine her marriage to an abusive husband and she plucks up the courage to leave him.

A surprise encounter with her first love, a rising Cantonese opera singer, brings a period of calm and joy. But when Meng proposes marriage, Xiu Yin backs off and he leaves for Hong Kong. It takes three years of loneliness and letter writing before they reunite again.