Mary Jane's Not a Virgin Anymore (1996)

Jane, a high school senior, feels like she doesn't belong either in the ultra-conservative suburbs where she lives with her always arguing parents, or downtown if only because some of her colleagues at the Victoria, the downtown art house movie theater where she works, are constantly reminding her that she's from the suburbs.

On an impromptu date with Steve, the "friend of a friend", Jane loses her virginity. The entire experience, which was both emotionally and physically bad, leaves Jane with bad taste about sex largely because she knows that Steve orchestrated the date to include sex without telling her. Beyond Matt - Steve's best friend - who she considers a boor, blowhard and drunkard, Jane confides in all her colleagues at the theater who she surveys about their first sexual experiences, those discussions when she learns their different and often misguided views of sex: Dave, her slightly older gay boss, whose first was somewhat different in he exploring his sexuality at the time; Ryan, the adorable geek who deep down Jane would have liked to be her first; party girl Grace who is hiding a not so secret secret associated with her sex life; and Ericka, the punk rocker who is also hiding a different kind of secret associated with her sex life. Things for Jane take a turn when Dave hires Tom, the proverbial good looking nice guy who shows an interest in her. Jane may have other things to think about in life as her movie theater colleagues and friends go through issues in their own lives.