Baseado nas experiências de milhares de pessoas ao redor do mundo, inclusive do próprio roteirista deste filme, O Homem da Escuridão conta a história de uma fotógrafa que acaba de se casar e é perseguida por um homem misterioso, que a segue em seus sonhos. Com sua sanidade no limite, a moça começa a ver a mesma figura sombria em vários lugares. Sem saber se é uma alucinação ou se é realidade, ela conhece um homem que alega saber a verdade sobre o tal personagem misterioso e aceita fazer uma experiência para tentar encontrá-lo. Quando o homem ultrapassa a barreira da realidade, o perigo vem.
Taiwanese successful actuary Chung Wen Kai lives a life free of any unnecessary risks, or calculated ones if any. Wen Kai plans to pay Sandra, his rich girlfriend who has been away in Singapore for a business trip, a surprise visit on Valentine’s Day. Wen Kai also plans to propose to Sandra. What Wen Kai did not plan for was to have lost the diamond ring at the airport. Wen Kai also did not plan to meet Haney Goh, whom Wen Kai will “partner” reluctantly in order to buy a new diamond ring for Sandra at couple-only 50% Valentine’s Day special discount at a jewellery shop in Singapore. While stepping out of the jewellery shop, the “couple” are robbed and Wen Kai loses all his valuables including a phone which Haney took to throw at the robbers. Feeling sorry for Wen Kai, Haney decides to help Wen Kai in completing his goal to propose to Sandra.
After graduating from high school, classmates Jerry and Lok move into an apartment together for the freedom to best explore all the best that the world can offer them: women. Jerry applies to be interviewed for a survey on dating, only to fall in love with interviewer So, even if she's more interested in data than dating. When Lok's sister, Foon, returns from Tibet, she moves in with the duo and soon she and Jerry are at each other's throats...
