Movie: Rushmore (1998)
Director: Wes Anderson
Stars: Jason Schwartzman, Bill Murray, Olivia Williams
Max Fisher (Jason Schwartzman), the protagonist of Rushmore, thinks he's older and wiser than he is. This is alternately charming and infuriating. And in one moment, it becomes the source of serious discomfort.
Max has fallen for a teacher, Rosemary Cross (Olivia Williams), at the prestigious private academy he attends. During their most heated conversation, Max tries to kiss her. Mind you, this is after she's made it quite clear to him that he can't have a relationship with her, that this is all the way wrong, and that he's acting like a brat. Tragic Max doesn't get it. When he goes in for the kiss, Ms. Cross pushes him, and he tumbles over a plastic bin.
This is where the second-hand embarrassment starts, with Max looking utterly pathetic. Then, Cross spells it out in the brutal language of middle school boys. "How would you describe it to your friends," she asks. "Would you say that you fingered me?" The word is perfectly calibrated to make the skin crawl. Max appears aghast, just like the viewer. â€”RS