This chapter explores women's nuanced relationships with romantic comedies, focusing on themes of internalized misogyny and societal norms. Through the lens of 'How to Lose a Guy in 10 Days,' the discussion critiques the perpetuation of harmful stereotypes while reflecting on nostalgic perceptions of young love and the absurdity of character dynamics. The speakers draw connections between these films and broader challenges in gender roles and emotional landscapes, offering insights into how these narratives shape real-world dating experiences.