Liza Weil in Whatever (1998)

A teen faces her impending adulthood in the carefree sex and drug revolution years of the early 80's prior to fears of AIDS. She lives with her bitter, divorced mother and her sadistic kid brother. Looking forward to a life based on her passion for art, she nevertheless gets in with the partying crowd which causes her to miss deadlines and poor grades which jeapordizes her future. Ultimately she ends up losing her virginity to an older artist wanna-be who she has had a long standing crush on.