The Downfall of Dating: Are We Looking for Love All Wrong? | Esther Perel

Renowned psychotherapist and relationship expert Esther Perel joins Maria Sharapova on Pretty Tough to explore why modern dating feels so exhausting and what makes long-term relationships lose their spark. Esther explains why dating has become more like a job interview, how the qualities we initially love about our partners can become sources of conflict, and what couples can do to break out of the same arguments.

She also shares her experience conducting couples therapy between a man and his AI girlfriend, raising questions about intimacy, infidelity, and the future of human connection. Plus, Esther shares why being the first to apologize can change the course of an argument.

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CHAPTERS00:00 — Introduction: Meet Esther Perel and the Evolution of Relationship Psychology

01:45 — Surviving vs. Living: The Existential Difference Between Being Alive and Fully Engaged

04:30 — The Power of Mentorship: How Esther Built Her Career Through Curiosity and Boldness

05:45 — From Clinician to Global Public Health Campaign: Why Relationships Need "Practice"

09:45 — The Art of Reflective Listening: Why Most People Only Listen for 10 Seconds

13:00 — Playing the Workplace Card Game: Esther’s Biggest Feedback Lesson

16:30 — Taking Therapy to the Big Screen: Inside the Movie The Invite and Penelope Cruz's Character

22:00 — Mating in Captivity: Reconciling the Eternal Paradox of Safety and Adventure

31:15 — Modern Dating Fatigue: Why the "Checklist" Approach Destroys Romance

40:00 — The First Human-AI Couples Therapy Session: Is Loving a Chatbot an Affair?

47:30 — Who Holds the Power? Why the Person Who Apologizes First Interrupts the Pattern

52:15 — Refusing to Choose: How Ambitious Women Can Hold Both Ambition and Vulnerability Without Burning Out

56:00 — The "Pretty Tough" Rapid-Fire Questionnaire: Unlearning Rumination and Embracing Directness

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About Pretty Tough

Pretty Tough is the weekly interview podcast hosted by five-time Grand Slam champion, entrepreneur, and bestselling author Maria Sharapova. Each week, Maria sits down with founders, CEOs, athletes, creatives, investors, and other high achievers for candid conversations about leadership, ambition, decision-making, performance, entrepreneurship, wellness, and building exceptional careers.Drawing from her own experience at the highest levels of sport and business, Maria explores what it really takes to succeed—from navigating failure and reinvention to scaling companies, leading teams, and pursuing excellence over the long term.

About Maria Sharapova

Maria Sharapova is a five-time Grand Slam champion, former World No. 1 tennis player, entrepreneur, investor, bestselling author, and one of the most recognizable athletes of her generation. Since retiring from professional tennis, she has built businesses, invested in consumer, technology, and lifestyle companies, and become a respected voice on leadership, performance, and entrepreneurship.

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