Three stories, interwoven, each exploring a different aspect of searching for love in the city of Los Angeles. The lead characters are interconnected, but not necessarily related, and each thread operates more or less independently. The first story explores the life of a 29-year-old virgin, Jenny, who desperately wants to lose her virginity before her 30th birthday. As she encounters one loser after another on dates, Jenny pines after her boss, Dustin. While at her grandmother's retirement home, Jenny learns a powerful lesson from her grandmother about sex and the meaning of life. The second explores two days in the life of Shane, the lead singer of the L.A. rock band Dirty Virgin. Shane has her pick of admirers but it's her roommate Dustin she wants to be with. Shane confesses having feelings for a "mystery man" on a radio show but when Dustin meets Cali, Shane's shot at love starts to dwindle.