Uploaded June 2026 | Updated September 2026, 2 weeks ago
Olivia Wilde (The Invite, Booksmart, and Don’t Worry Darling) is a director, actor, and filmmaker. Olivia joins Armchair Expert to discuss being raised by war-correspondent parents, growing up too fast on the Georgetown campus, and finding her footing at boarding school. Olivia and Dax talk about learning the wrong lessons in LA audition rooms, leaving The OC to chase movies, and making the jump from directing music videos to Booksmart. Olivia explains why the most personal work is usually the best work, how parenting teaches patience and humility, and why we need to relearn the art of disagreement.
Watch the fact check: youtu.be/IObbNUdfxgI
Check Allstate first for a quote that could save you hundreds: allstate.com
Watch Armchair Expert episodes: youtube.com/playlist?list=PLzPEuwClyOzDdlrAmU-IwKncG87qrF7Vw
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About the Show:
Hi, I’m Dax Shepard, and I love talking to people. I am endlessly fascinated by the messiness of being human, and I find people who are vulnerable and honest about their struggles and shortcomings to be incredibly sexy. I invite you to join me as I explore other people’s stories. We will celebrate, above all, the challenges and setbacks that ultimately lead to growth and betterment. What qualifies me for such an endeavor? More than a decade of sobriety, a degree in Anthropology and four years of improv training. I will attempt to discover human “truths” without any laboratory work, clinical trials or data collection. I will be, in the great tradition of 16th-century scientists, an Armchair Expert.
Watch Armchair Expert every MONDAY, WEDNESDAY, and FRIDAY here on Youtube!
Listen to episodes ad-free by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/shows/armchair-expert-with-dax-shepard
Chapters:
0:00 - Olivia Made a Mike Nichols Movie
9:00 - Remembering Your Childhood
15:55 - Triple Citizen
24:40 - Intellectual Salon
30:45 - Boarding School
38:49 - The Skill of Disagreeing
49:53 - Casting Intern
59:09 - Acting Career
1:09:51 - Booksmart
1:15:29 - Thank You, Darling
1:25:32 - Sexuality on Screen
1:30:39 - The Content Inferno
1:35:39 - The Invite
1:48:22 - How Do We Survive Relationships?
2:03:07 - Laughing About How Ridiculous We Are
#armchairexpert #daxshepard #oliviawilde #theinvite #dontworrydarling
Olivia Wilde (The Invite, Booksmart, and Don’t Worry Darling) is a director, actor, and filmmaker. Olivia joins Armchair Expert to discuss being raised by war-correspondent parents, growing up too fast on the Georgetown campus, and finding her footing at boarding school. Olivia and Dax talk about learning the wrong lessons in LA audition rooms, leaving The OC to chase movies, and making the jump from directing music videos to Booksmart. Olivia explains why the most personal work is usually the best work, how parenting teaches patience and humility, and why we need to relearn the art of disagreement.
Watch the fact check: youtu.be/IObbNUdfxgI
Check Allstate first for a quote that could save you hundreds: allstate.com
Watch Armchair Expert episodes: youtube.com/playlist?list=PLzPEuwClyOzDdlrAmU-IwKncG87qrF7Vw
Follow Armchair Expert on social:
instagram.com/armchairexppod
facebook.com/ArmchairExpPod
twitter.com/armchairexppod
Connect with Wondery
wondery.com/shows/armchair-expert-with-dax-shepard
facebook.com/WonderyMedia
twitter.com/WonderyMedia
instagram.com/WonderyMedia
tiktok.com/@wonderymedia
About the Show:
Hi, I’m Dax Shepard, and I love talking to people. I am endlessly fascinated by the messiness of being human, and I find people who are vulnerable and honest about their struggles and shortcomings to be incredibly sexy. I invite you to join me as I explore other people’s stories. We will celebrate, above all, the challenges and setbacks that ultimately lead to growth and betterment. What qualifies me for such an endeavor? More than a decade of sobriety, a degree in Anthropology and four years of improv training. I will attempt to discover human “truths” without any laboratory work, clinical trials or data collection. I will be, in the great tradition of 16th-century scientists, an Armchair Expert.
Watch Armchair Expert every MONDAY, WEDNESDAY, and FRIDAY here on Youtube!
Listen to episodes ad-free by joining Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/shows/armchair-expert-with-dax-shepard
Chapters:
0:00 - Olivia Made a Mike Nichols Movie
9:00 - Remembering Your Childhood
15:55 - Triple Citizen
24:40 - Intellectual Salon
30:45 - Boarding School
38:49 - The Skill of Disagreeing
49:53 - Casting Intern
59:09 - Acting Career
1:09:51 - Booksmart
1:15:29 - Thank You, Darling
1:25:32 - Sexuality on Screen
1:30:39 - The Content Inferno
1:35:39 - The Invite
1:48:22 - How Do We Survive Relationships?
2:03:07 - Laughing About How Ridiculous We Are
#armchairexpert #daxshepard #oliviawilde #theinvite #dontworrydarling
