Dochinpira 14: A Hitman's Affair (1995)

On another day as a professional seducer, Jin receives a bizarre request from a slick businessman: steal his girlfriend’s heart so she’ll break up with him. Sounds easy, until Jin meets Kanae, a cold, stunning beauty… who happens to be the daughter of a powerful yakuza boss. Things gotten worse when Yuri, a sultry hostess from the apartment next door, latches onto Jin with relentless desire. But the real danger surfaces when Jin discovers the businessman is actually a gangster in disguise plotting an assassination against Kanae’s father.