How to Be a Player

"How to Be a Player" is a 1997 American sex comedy film that tells the story of Drayton "Dray" Jackson, a young playboy with a singular objective: to have sex with as many women as possible without getting caught by his girlfriend Lisa. His sister Jenny and her friend Katrina take matters into their own hands, hosting a party in Malibu where all of Dray's girlfriends are invited, with the intention of exposing him for the player he is. In the end, Dray learns that when put in a hostile environment, a "player" doesn't reform - he adapts.