Armchair Expert with Dax Shepard

Podbit · Armchair Expert with Dax Shepard

Olivia Wilde

Explore episode Jun 29, 2026
Arts
Andover's Theater Program and the Birth of a Director

Olivia Wilde · Jun 29, 2026 Arts

Phillips Academy Andover had a mainstage theater, multiple black box spaces, and a student-producer program. Olivia Wilde produced 12 plays in a single year — essentially doing college-level creative work at 15. That's where the director was born.

Where this was said

Georgetown Campus, Getting Sent to Boarding School, and Why She's Glad She Was

At 37:24 · chapter starts 28:20

This chapter covers a crucial formative arc. Olivia describes growing up in Washington DC feeling like she was 24 at age 13 — haunting the Georgetown campus, pretending to be a college student with invented majors, attending the 930 Club music venue past curfew. She had her braces removed at 13 because they made her 'look young.' Her parents, she says, could see where this was heading and sent her to Andover boarding school. She initially resists the implication that this was a punishment, but concedes that DC was a hard town for a precocious 13-year-old. The boarding school turned out to be transformative: Andover had a mainstage theater, multiple black box and studio spaces, and a student-producer program. Olivia produced 12 plays in a single year. She got into Bard College, deferred three times, and never went.

Society & Culture
Boarding School, Georgetown, and Growing Up Way Too Fast

Olivia Wilde · Jun 29, 2026 Society & Culture

Olivia Wilde grew up on the Georgetown campus making up college majors to impress older students, got her braces removed at 13 because they made her look young, and was snuck to boarding school at Andover partly to save her from herself. She now says it was the best thing that ever happened to her.

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