It all creates a sense of entitlement that initially comes off as confidence, but things change when Max starts to get rejected in his attempts at romance with Ms. Cross (Olivia Williams). As she refuses to reciprocate his schoolboy crush, Max reveals the spoiled child that hides under the façade of an assured young man. Max treats Ms. Cross as if she owes him something simply because he likes her and has done uninvited favors for her. The men in her life, like Dr. Flynn (Luke Wilson) and, later, Herman Blume (Bill Murray, in his first appearance in a Wes Anderson film), are constantly harassed and bullied by Max. His romantic pursuit, if you can really call it that, is ruthlessly and desperately persistent. It’s led romantic and more about his irritation that Cross has not dropped everything and centered her life on Max’s wants and needs.

The film doesn’t forgive Max for his transgressions, though. He slowly loses everything he values in his life as he keeps behaving in such abhorrent ways. He’s expelled from Rushmore for trying to build an aquarium in Cross’s honor on school grounds without the school’s permission or knowledge. His repellent, foolish, over-the-top actions obviously repel Cross completely, and he loses a friend in Blume for similar reasons. At his lowest point, Max even loses the motivation to keep going to his public school and works full-time in his father’s barbershop. After this period of penance, things only begin to turn around for Max as he learns to humble himself and consider other perspectives than just his own male gaze. He apologizes to fellow students he mistreated, then works with them to use his greatest skill, producing plays, to make things right with those he’s wronged more severely. Through his Vietnam War piece, 'Heaven and Hell', he honors Blume’s military experience and gives roles to students with whom he’d once been at odds. The play also is dedicated to the memory of Ms. Cross’s deceased husband, Edward Appleby, as way of apology to Ms. Cross for his disrespect. Cross and Blume are sat together by Max’s arrangement, which allows them to discuss what went wrong in their relationship and decide to give it another try. Through his humility and repentant gestures, Max actually earns the trust that was freely given before, and that work is what makes it mean so much more.