When Will I Be Loved (2004)

Synopsis
Directed by James Toback, the erotic drama When Will I Be Loved? revolves around Vera, the debutante girlfriend (Neve Campbell) of a fast-talking hustler (Frederick Weller) who is on the verge of making millions through a big-money gambling venture. Feeling undervalued, Vera explores her sexuality through whatever means she can think of, including explicit discussions with a potential employer, picking up random men, and videotaping steamy trysts with her female lover. When Ford (Weller) proposes that Vera spend the night with Italian media mogul Count Tommaso (Dominic Chianese), who is willing to put up 100,000 dollars for the occasion, Vera concocts a scheme to show both men what her true worth really is. ~ Tracie Cooper, All Movie Guide