Loving Jezebel (1999)

Writer-director Kwyn Bader's debut feature is an extremely likeable romantic comedy that features a star-making performance from Hill Harper. Harper plays Theodorus Melville, a mixed-race suburban youth who discovers at an early age that he has a penchant for falling in love with the wrong girls--most often, his friends' girlfriends. Barely surviving college, where he slept with the girlfriend of the football team's star running back, Theodorus eventually settles in New York City with his best friend, whose gorgeous Trinidadian girlfriend, Mona (Sandrine Holt), can't hide her attraction for him. Meanwhile, Theodorus is in the midst of a passionate affair with Frances (Nicole Ari Parker), a firecracker of an actress whose mental stability is questionable. Working as a waiter in a coffee shop, Theodorus befriends the bumbling Samantha (Laurel Holloman), a sweet-natured woman who is married to Gabe (David Moscow), a walking time bomb. By the time that Theodorus has an epiphany which enables him to fully give in and choose his truest love, his philandering ways threaten to catch up with him once and for all.