Reclaiming with Monica Lewinsky

All year long, people have asked Monica the same question: Who’s been your favorite interview? And all year long, the truth has been the same — there was something unforgettable in every single conversation. So for this special compilation, we’ve pulled together some of the most powerful, lingering moments of 2025 into one episode.
From Miley Cyrus talking about shame, sexuality, and the collateral damage of fame, to Alan Cumming confronting his abuser, to Chelsea Handler cracking open decades of armor over a single orange — these are the stories that stayed with us. Jurnee Smollett and Gabrielle Union explore blood memory and ancestry; Mark Duplass names “the woog” that lives between anxiety and depression; Sarah Paulson and Allison Janney reflect on childhood survival strategies and the characters that shaped them. Tarana Burke reframes grace, John Oliver and Margaret Cho show how gallows humor can literally save us, Molly Ringwald and Adam Scott unpack the long tail of fame, Olivia Munn reclaims her mastectomy scars, Beanie Feldstein talks about grief and language, Jon Chu and Tony Hawk share the hustles and crash landings behind their legends, and Elise Loehnen and Courtney Smith dig into the high cost of reputational harm — especially for women.
And because Reclaiming is never just one thing, we even tucked some of the year’s funniest, most unhinged moments at the end — from sex vocabulary lessons to Broadway “up the butt” lore to John Oliver’s favorite four-letter word. It’s a season of memorable moments, in one episode: raw, reflective, heartbreaking, and laugh-out-loud ridiculous in all the best ways.

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This week on Reclaiming, we sit down with Michael Urie—actor, producer, and director whose career has been shaped by sharp comedy, emotional range, and a deep love of the stage and screen. In this conversation, Michael reflects on the lasting impact of Ugly Betty, what it meant to play a character who resonated so deeply with audiences, and how those early television years helped define his voice as a performer. He opens up about his unconventional path into acting—the power of the ACT after bombing the SATs—and how that second chance ultimately led him to Juilliard, along with the expectations and stereotypes that often come with elite training.
We also explore his annual festival Pride Plays and why creating intentional space for LGBTQ+ artists feels increasingly vital in a media landscape dominated by algorithms and influencers. And just in case things get too serious, Michael also gives Monica permission to call him “Mikey,” finishes the rest of her banana, and proves once and for all that Mikey will eat anything.

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This week on Reclaiming, Monica sits down with author Elise Loehnen and coach Courtney Smith for a conversation about goodness, desire, and the new "workbook" they co-authored "Choosing Wholeness Over Goodness" . Elise reflects on the ideas behind her other book “On Our Best Behavior” and the cultural pressure for women to be selfless, disciplined, and “good,” while Courtney explains how those inherited beliefs settle into the body and quietly steer our choices. Together they explore Enneagram types and how understanding our dominant type and wing can illuminate the fears driving our behavior, the drama triangle and the roles we slip into without noticing, and the surprising insight within envy and wanting. They talk about the fear of losing approval when we step out of line, the shame that gathers around desire, and the courage it takes to name what we truly need.

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This week on Reclaiming, Monica sits down with bestselling author Harlan Coben for a conversation about risk, and the emotional heart that anchors every twist he writes. Harlan reflects on the fear and curiosity that led him to co-author a book with Reese Witherspoon, the childhood losses that shaped his most beloved characters, and the belief that pressure is a privilege for any creative life. He opens up about the hotel key he still keeps from his father, why thrillers only work when readers care deeply, and how boredom, insecurity, and paying attention to human behavior quietly fuel his work. Together, they explore grief, humor, the lives we imagine, and the stories that keep us tethered to one another.
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This week on Reclaiming, Monica sits down with the authors of ALL THE COOL GIRLS GET FIRED, Laura Brown and Kristina O’Neill, for a conversation about identity, resilience, and rebuilding after everything shifts. Laura and Kristina share the story of being fired from their dream jobs, how they moved through shock and uncertainty, and why that moment became the spark for their next chapter. Together, they explore how women are taught to carry shame around career loss, the power of community and humor in hard moments, and what it really means to reclaim your worth outside of a title. Sharing the firing stories of famous women like Oprah, Katie Couric, Carol Burnett and many others, It it is an honest, grounded look at letting go, starting again, and trusting that sometimes the fall is what sets you free.

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