In 1960 Hong Kong, Yuddy, Leslie Cheung a smooth-talking playboy, seduces Li-zhen, Maggie Cheung but shows little interest in a lasting romance, leaving her heartbroken. He soon moves on to Mimi, a vivacious cabaret dancer. Zeb, Jacky Cheung, is drawn to Mimi, but his affections are not returned. Behind the glitter, Yuddy's bond with his adoptive mother, Rebecca, Rebecca Pan, a former prostitute, is strained by a long refusal to reveal the identity of his birth mother.
Li-zhen finds solace in Tide, Andy Lau a steady policeman who walks the rounds near Yuddy's apartment. Tide dreams of a sailor's life, yet he remains in the police force to care for his ailing mother. Li-zhen opens up about a heartbreak, her successful cousin's upcoming marriage, and a longing for home in Macau. She promises Tide a free ticket to a football match of his choice, and Tide responds with a simple habit: if she needs someone to talk to, she should call him from the phone booth he passes every night. After his mother dies, Tide leaves Hong Kong to pursue the sea.
Rebecca eventually reveals to Yuddy that his birth mother lives in the Philippines. With that knowledge, Yuddy departs to search for her, handing his car to Zeb and leaving Mimi behind. A despondent Mimi resolves to follow him. Zeb, who still loves Mimi, sells Yuddy's car to fund her journey and tells her to come back if she does not find him.
Yuddy traces his mother to a Philippine home, but she refuses to see him, leaving him with the ache of a connection denied. On a stopover in the Philippines, Tide finds a drunk Yuddy on the street and brings him to his hotel room. Yuddy does not recognize Tide at first, yet he accepts the help. A moment of danger erupts at a railway station when a payment dispute over a fake American passport escalates into violence; Tide intervenes, and the two manage to escape by train. Tide asks Yuddy if he recalls what happened on 16 April 1960 at 3 p.m., the moment he had asked Li-zhen to remember at the start of their courtship, and Yuddy says he does, but suggests it may be best to tell Li-zhen that he does not. When Tide steps away to talk with the train conductor, he returns to find Yuddy fatally shot.
A final sequence unfolds with Mimi arriving in the Philippines, Li-zhen closing the ticket stall, and a phone ringing in the booth. The film ends with a lingering image of a slick young man, smoking and preparing himself in a darkened room, leaving the story paused on memory, longing, and what might have been.