Uploaded June 2026 | Updated September 2026, 1 hour ago
A recent session was a threshold moment for Esther where she found herself doing couples therapy with a man and his AI companion. To explore the questions it raised, Esther sits down with New York Times technology reporter, Kashmir Hill, who has spent years reporting on the growing world of AI relationships. They explore the psychological pull of these systems, the design choices behind them, and the deeper human needs they tap into. When a chatbot can mirror your thoughts, validate your feelings, and never turn away, where does connection end and illusion begin?
Please note, the Times sued OpenAI in 2023, accusing it of copyright infringement. The company has denied those claims.
Chapters
00:00 What Happens When an AI Understands You Better Than People?
01:37 Is Falling for AI Just Roleplay or Something More Real?
02:31 When Does an AI Stop Being a Tool and Become a Companion?
03:24 Why Did Ayrin Fall in Love With Leo?
04:15 What Makes an AI Relationship Feel So Safe?
05:30 Are You Falling in Love With AI or With Yourself?
08:06 What Happens When Your AI Forgets You Overnight?
10:02 Why Would Someone Leave an AI for a Human Relationship?
11:08 What Can Human Love Offer That AI Can’t?
13:23 Why Did Antonio Choose His AI Companion Over People?
15:40 Should an AI Be Able to Reject You?
17:55 Who’s Really in the Relationship You or the Company Behind the Bot?
19:34 What Are You Giving Away When You Confide in AI?
20:43 Can AI Become Part of a Polyamorous Relationship?
22:00 Is Talking to an AI Companion a Form of Cheating?
23:20 Is AI Romance More Like Porn or Betrayal?
23:34 When Does an AI Relationship Become “Real” Love?
24:05 Is AI Changing the Meaning of Love and Ethics?
25:49 Can Love Exist Without Reciprocity?
27:25 Are AI Companions Designed to Keep Us Addicted?
29:27 Why Does Text-Based AI Feel So Intimate?
31:56 Do AI Companions Cure Loneliness or Deepen It?
34:31 How Do We Keep AI From Replacing Human Connection?
36:29 Are We Turning AI Into a Spiritual Oracle?
39:25 What Happens When We Hand Our Agency Over to AI?
42:44 Will AI Bring Us Closer Together or Further Apart?
About Where Should We Begin?:
Every Monday morning, step into the office of iconic psychotherapist Esther Perel and listen in as real people in search of insight bare the raw, intimate, and profound details of their stories. From breakups and open relationships to workplace conflicts and fractures in the family, it’s a place to hear our own stories reflected in the lives of others.
About Esther Perel:
Psychotherapist, relationship expert, and New York Times bestselling author Esther Perel is recognized as one of today’s most insightful and original voices on modern relationships. Fluent in nine languages, she helms a therapy practice in New York City and serves as an organizational consultant for Fortune 500 companies around the world. Her celebrated TED Talks have garnered more than 40 million views and her bestselling books, Mating in Captivity and The State of Affairs, are global phenomena translated into more than 30 languages. Esther is also the host of the hit podcast Where Should We Begin? which is available on Apple Podcasts. Learn more at EstherPerel.com or subscribe to her Substack Entre Nous for bonus content.
A recent session was a threshold moment for Esther where she found herself doing couples therapy with a man and his AI companion. To explore the questions it raised, Esther sits down with New York Times technology reporter, Kashmir Hill, who has spent years reporting on the growing world of AI relationships. They explore the psychological pull of these systems, the design choices behind them, and the deeper human needs they tap into. When a chatbot can mirror your thoughts, validate your feelings, and never turn away, where does connection end and illusion begin?
Please note, the Times sued OpenAI in 2023, accusing it of copyright infringement. The company has denied those claims.
Chapters
00:00 What Happens When an AI Understands You Better Than People?
01:37 Is Falling for AI Just Roleplay or Something More Real?
02:31 When Does an AI Stop Being a Tool and Become a Companion?
03:24 Why Did Ayrin Fall in Love With Leo?
04:15 What Makes an AI Relationship Feel So Safe?
05:30 Are You Falling in Love With AI or With Yourself?
08:06 What Happens When Your AI Forgets You Overnight?
10:02 Why Would Someone Leave an AI for a Human Relationship?
11:08 What Can Human Love Offer That AI Can’t?
13:23 Why Did Antonio Choose His AI Companion Over People?
15:40 Should an AI Be Able to Reject You?
17:55 Who’s Really in the Relationship You or the Company Behind the Bot?
19:34 What Are You Giving Away When You Confide in AI?
20:43 Can AI Become Part of a Polyamorous Relationship?
22:00 Is Talking to an AI Companion a Form of Cheating?
23:20 Is AI Romance More Like Porn or Betrayal?
23:34 When Does an AI Relationship Become “Real” Love?
24:05 Is AI Changing the Meaning of Love and Ethics?
25:49 Can Love Exist Without Reciprocity?
27:25 Are AI Companions Designed to Keep Us Addicted?
29:27 Why Does Text-Based AI Feel So Intimate?
31:56 Do AI Companions Cure Loneliness or Deepen It?
34:31 How Do We Keep AI From Replacing Human Connection?
36:29 Are We Turning AI Into a Spiritual Oracle?
39:25 What Happens When We Hand Our Agency Over to AI?
42:44 Will AI Bring Us Closer Together or Further Apart?
About Where Should We Begin?:
Every Monday morning, step into the office of iconic psychotherapist Esther Perel and listen in as real people in search of insight bare the raw, intimate, and profound details of their stories. From breakups and open relationships to workplace conflicts and fractures in the family, it’s a place to hear our own stories reflected in the lives of others.
About Esther Perel:
Psychotherapist, relationship expert, and New York Times bestselling author Esther Perel is recognized as one of today’s most insightful and original voices on modern relationships. Fluent in nine languages, she helms a therapy practice in New York City and serves as an organizational consultant for Fortune 500 companies around the world. Her celebrated TED Talks have garnered more than 40 million views and her bestselling books, Mating in Captivity and The State of Affairs, are global phenomena translated into more than 30 languages. Esther is also the host of the hit podcast Where Should We Begin? which is available on Apple Podcasts. Learn more at EstherPerel.com or subscribe to her Substack Entre Nous for bonus content.
