How did Rob Reiner redefine rom-coms and the role of romance in action adventure movies? In light of the recent tragic death of Michele and Rob Reiner, Mandy Kaplan joins Matthew to talk about his legacy and then examine two defining films from the director: When Harry Met Sally... (1989) and The Princess Bride (1987). One asks whether men and women can be friends; the other explores what “true love” actually means. Together, they reveal Reiner’s unique approach to romantic storytelling and the moral questions embedded in how we connect with others.We explore how When Harry Met Sally... uses Sally’s rigid control and Harry’s defensive cynicism to examine self-deception and emotional availability, while The Princess Bride employs fairy tale structure to investigate devotion, sacrifice, and the nature of romantic commitment. Both films challenge conventional rom-com formulas to ask deeper questions about authenticity, vulnerability, and what we owe each other.Questions We Discussed

• Can men and women actually be friends without sex complicating things, and how does When Harry Met Sally... answer this question?
• How does The Princess Bride define “true love” differently than typical romantic stories?
• How does Westley and Buttercup’s relationship in The Princess Bride model devotion and sacrifice?
• What makes Rob Reiner’s approach to romantic comedy distinct from other directors in the genre?
• How do both films explore the relationship between friendship and romantic love?
• Does The Princess Bride’s fairy tale framework allow it to examine love more honestly than realistic rom-coms?
• What role does vulnerability play in the ethical transformation of characters in both films?

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