Woo (Smith) is an extroverted woman living in New York City, and she has a notorious knack for turning men into mush. When Woo's psychic friend Celestrial (Girlina) predicts that the man of her dreams is about to enter her life, Woo doesn't believe it is true. Celestrial, however, is convinced that Woo is destined to meet a tall, debonair Virgo. Woo's cousin Claudette (Paula Jai Parker) and Claudette's boyfriend Lenny (Dave Chappelle) plan to spend the night together but find themselves entertaining Woo instead. Lenny begs his best friend Tim Jackson (Davidson) to take Woo out - even though shy, strait-laced law clerk Tim is the polar opposite of the sassy and brassy Woo. That same night, Lenny and Claudette's night goes wrong when his sick obsession with chicken drives her to be forced to dress up as a sexy but awkward "chicken ho" (he makes her cluck and walk like a chicken) but she is allergic to feathers.