When Kathryn discovers that Sebastian has developed feelings for the Headmaster’s daughter, the chaste and virtuous Annette Hargrove (Reese Witherspoon), she is disgusted. To punish him for his sentimentality, she proposes a wager. If Sebastian can seduce and publicly humiliate Annette before the start of the school year, Kathryn will grant him one night with her—the ultimate prize he has always craved. But if he fails, Sebastian loses his beloved vintage Jaguar.
She walks away.
If you search for , you will find endless analysis of its fashion. And for good reason. Costume Designer Denise Wingate uses clothing as a character map.
The keyword continues to trend not out of simple nostalgia. It resurges because every generation discovers the cold, glossy horror of the Upper East Side. With a television reboot in development (as of 2025) and the film streaming on multiple platforms, new viewers are realizing that this is not a teen comedy. It is a tragedy of manners, drugs, and devastating one-liners.
As the story unfolds, the characters' personalities and motivations are expertly revealed through their dialogue and interactions. Sebastian, played by Ryan Phillippe, is a complex and intriguing character, whose façade of confidence and control slowly cracks to reveal a vulnerable and insecure individual. Kathryn, on the other hand, is a masterfully crafted villain, whose sharp wit and intelligence make her a formidable opponent.
But something shifts. One night, Sebastian and Annette are caught in a rainstorm. They take shelter in an abandoned greenhouse. Annette, shivering, looks at him and says, “You’ve never let anyone see you cry, have you?”
No article about would be complete without acknowledging the soundtrack. It remains one of the most iconic of the decade.
Sebastian tries to explain, but the truth is ugly. He admits the wager. He admits everything except the one thing that matters: that he loves her now.
