Strange Fits of Passion (1999)

The hilarious tale of one young woman's quest to lose her virginity. She is a sexually curious, romantically frustrated bookstore clerk on a mission. Taking the advice of her friends she goes from one person to the next in her vain attempts to be deflowered. In between encounters with other people, she returns to the one person she can trust and truly relate to, her gay friend Jimmy, whose faith in love is being shake by the revelation that his boyfriend has been unfaithful.