Set in 1960's Hong Kong, the story centers around the Troubled Yuddy/York (Leslie Cheung), a bad boy in the All Girls Want Bad Boys sense who seduces women into loving him then mistreats them until they leave him. The film starts with his romance with demure concession stand girl Su Lizhen (Maggie Cheung), and after their breakup to his seamlessly picking up feisty hooker Mimi. The story also deals with York's dysfunctional relationship with his adoptive mother Rebecca (Rebecca Pan), an aging prostitute whose crass emotional extortion over his Missing Mom has left him with much of the emotional baggage that makes him mistreat women.
The rest of the film deals with York, Lizhen , Mimi, Nice Guy cop Tide (Andy Lau) and York's Dogged Nice Guy friend Leb (Jacky Cheung) dealing with the emotional fallout of these relationships while York chases down a lead on his biological mom's whereabouts.
This film contains examples of:
- All Girls Want Bad Boys: York's cocky attitude and good looks.
- Betty and Veronica: Lizhen as Betty with Mimi as Veronica. Notably, Lizhen doesn't want York back (even though she still has feelings for him), tells Mimi as much and warns her about what he can do.
- The Cameo: Tony Leung Chiu-wai appears at the end of the movie for about ten seconds before the credits rolls.
- Did You Think I Can't Feel?: Lizhen to York... who does think she can feel, but doesn't care.
- Dogged Nice Guy Leb to Mimi, who he has no chance with because she's still in love with York (and knows this), so he sells his car so she can chase down York and realize what a cad he is, hoping to the outside chance he'll be the rebound guy.
- Dysfunction Junction: Many of the characters have — or get — an emotional hangup over the course of the movie.
- Even Bad Men Love Their Mamas: York with Rebecca and his biological mother, despite the former's manipulation and the latter's absence. That being said, York is willing to cut all contact with Rebecca to learn his mom's location.
- Even Evil Has Standards: Though York is a cad, he never physically abuses his lovers, won't steal from them, and even outright tells them he's going to use them... and they put up with it!
- The Gunslinger: Tide (Andy Lau), who spends most of the movie as a fairly stoic beat cop who never brandishes a weapon, only to efficiently mow down a gang later in the movie... much to his own horror.
- Hooker with a Heart of Gold: Mimi. While she's very bossy and would normally be The Vamp, when paired with York she's actually his sugar momma.
- Inner Monologue: Every character gets one monologue explaining their thoughts and feelings up to that point, evenly spaced throughout the movie.
- Single Woman Seeks Good Man: By the end of the film Lizhen has healed enough that she calls the phone box that Tide says he walks by on patrol. Since he's now a sailor, it's fairly wishful to think they'll actually hook up, though of all the leads the two of them are the ones to have changed the most.
- The Sociopath: York has shades of this. While there are some lines he won't cross in Love, he's also all too willing to kill a man rather than pay the price of a forged passport.
- Soiled Dove: Averted with Rebecca, who toys with York by dangling the name and location of his biological mother over his head to keep him near.
- What the Hell, Hero?: Tide to York after the latter murders a man to avoid paying for a forged passport.
- You All Share My Story: All the characters are interconnected mutually, meeting up unexpectedly with shared connections and not realizing it.