Katherine Dee, an author and former dating advice columnist, shares her insights on modern dating dynamics shaped by technology and social media. She discusses how dating experiences can differ dramatically across locations like San Francisco and New York. The conversation dives into the prevalence of 'situationships' and avoidant behavior among younger generations. Dee also examines the cultural implications of the Me Too movement and evolving views on masculinity and femininity, highlighting the fragmented nature of contemporary relationships.