

QUESTION EVERYTHING
PRETTYSMART
Behind every headline is a person + a deeper story. Question Everything with journalist Danielle Robay cuts through social media buzz to uncover the voices, ideas, and cultural moments that shape how we see the world. Each week, she asks bold questions that challenge assumptions and reveal the nuance behind the narratives, inviting you to look closer at the world, and at yourself. Because there’s always more to the story.
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Danielle is also the creator of the bestselling QUESTION EVERYTHING card game series, which has sparked connection and conversation in thousands of living rooms around the world. She’s also the co-executive producer (alongside Reese Witherspoon) and host of Bookmarked by Reese’s Book Club. With her signature curiosity—dubbed “The Queen of Questions”—and a background in political science, Danielle brings both heart and rigor to every conversation. A Gloria Steinem Fellow and mentee of Larry King, she’s carried forward a legacy of curiosity and connection, interviewing icons from Taylor Swift to Malala Yousafzai in more than 8,000 hours of elevated conversation.
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Danielle is also the creator of the bestselling QUESTION EVERYTHING card game series, which has sparked connection and conversation in thousands of living rooms around the world. She’s also the co-executive producer (alongside Reese Witherspoon) and host of Bookmarked by Reese’s Book Club. With her signature curiosity—dubbed “The Queen of Questions”—and a background in political science, Danielle brings both heart and rigor to every conversation. A Gloria Steinem Fellow and mentee of Larry King, she’s carried forward a legacy of curiosity and connection, interviewing icons from Taylor Swift to Malala Yousafzai in more than 8,000 hours of elevated conversation.
Episodes
Mentioned books

Oct 23, 2025 • 1h 41min
Why 73% of Divorces Are Filed by Women +: Why Social Media is Causing Divorce with James Sexton (Divorce Attorney)
What if the best way to understand marriage is to talk to the person who sees it fall apart every day? In this episode, Danielle sits down with James Sexton, a high-stakes divorce attorney, bestselling author, and the man clients describe as “the sociopath you want on your side.” After 25 years and thousands of cases, Sexton has witnessed love at its breaking point + is sharing the unfiltered lessons that most couples never learn until it’s too late. From prenups to cheating, social media to second marriages, he reveals what really destroys relationships—and what actually keeps them alive. This conversation goes way beyond the courtroom; into love, fragility, human complexity, and why marriage is both the riskiest and most rewarding gamble you’ll ever take. James Sexton shares: The biggest mistakes that lead to divorce (and how to avoid them) Why 73% of divorces are initiated by women + what that really means The shocking truths about love, sex, cheating, and forgiveness he’s seen firsthand Why your spouse’s social media feed might be the biggest threat to your marriage What “high conflict” divorce really looks like (and why most divorces aren’t that) How money complicates marriage The simple but overlooked practice that could save your relationship Why every marriage ends in either death or divorce What second marriages teach us about doing it right the first time Why James believes love isn’t permanent…it’s on loan Follow James Sexton on Instagram: @nycdivorcelawyer Explore his book How to Stay in Love Check out Trusted Prenup Book Rec: All the Light We Cannot See by Anthony Doerr + Unworld by Jason Green

Oct 16, 2025 • 55min
The Greatest Lie Women Were Ever Told About Sex: with Cindy Eckert
What happens when a woman refuses to take no for an answer—from the FDA, from society, from stigma? In this episode, Danielle + Cindy Eckert, the billion-dollar entrepreneur and founder of Sprout Pharmaceuticals, who fought the U.S. government to bring the first FDA-approved drug for women’s sexual desire to market. Together, they unpack how women’s health, equality, and pleasure became a battleground and why the future of feminism might start in your doctor’s office. Cindy shares: The “lightning bolt” moment she realized women’s desire is rooted in brain chemistry, not emotion How Viagra was approved in 6 months while her drug took 6 years + what that says about systemic bias The truth about medical gaslighting and why women are still understudied and undervalued in healthcare Why she bought back her billion-dollar company to finish what she started How to know when your idea is worth fighting for (and when to walk away) The power of curiosity, candor, and crying in business Her advice for women who want impact, not just success The childhood disruption that made her fearless and independent Why women deserve pleasure, not permission Follow Cindy on Instagram @cindypinkceoBook recommendation: The Five Temptations of a CEO by Patrick Lencioni Learn more about her mission and work at The Pink Ceiling and Sprout Pharmaceuticals Disclaimer for ADDYI: ADDYI is for premenopausal women with acquired, generalized hypoactive (low) sexual desire disorder who have not had problems with low sexual desire in the past, and who have low sexual desire no matter the type of sexual activity, the situation or the sexual partner. The low sexual desire is troubling to them and is not due to a medical or mental health problem, problems in the relationship or medicine or other drug use. ADDYI is not for use in men or to enhance sexual performance. Your risk of severe low blood pressure and fainting is increased if you drink 1-2 standard alcoholic drinks close in time to your ADDYI dose. Wait at least 2 hours after drinking before taking ADDYI at bedtime. Your risk of severe low blood pressure and fainting is also increased if you take certain prescription, over the counter or herbal medications, or have liver problems. Low blood pressure and fainting can happen when you take ADDYI even if you don’t drink alcohol or take other medicines. Do not take if you are allergic to any of the ingredients in ADDYI. Allergic reactions may include hives, itching or trouble breathing. Sleepiness, sometimes serious, can occur. Common side effects include dizziness, nausea, tiredness, difficulty falling asleep or staying asleep and dry mouth. See full PI and Medication Guide, including Boxed Warning at addyi.com/pi or call 844-PINK-PILL.

Oct 9, 2025 • 1h 1min
Cancelled: The Dark Side of Wellness Culture with Lee Tilghman (Lee From America) and Leigh Stein
What really happens when the internet turns on you + you’re CANCELED? Danielle sits down with Lee Tilghman (aka @LeeFromAmerica), once one of Instagram’s first and biggest wellness influencers and now the author of the new memoir If You Don’t Like This, I’ll Die. Joining her is bestselling author and internet expert Leigh Stein, whose satire Self Care eerily mirrored Lee’s real-life unraveling before they had ever met. Together, they unpack the rise, fall, and reinvention of Lee—and what their stories reveal about cancellation, consumerism, feminism, and the cost of turning your life into a brand. Lee and Leigh share: The rise and fall of @LeeFromAmerica + the truth behind her “cancellation” Why women often cancel women (and what that says about power, belonging, and feminism) How influencer culture shifted from smoothies and self-care to social justice and “performative activism” The hidden costs of turning your personal life into a brand The cycle of consumerism, outrage, and burnout that traps us online The role of mob mentality and snark communities in shaping influencer culture Why wellness can be both a lifeline and a lie + how to find balance offline The loneliness of influencer fame, and why it can feel so isolating at the top Why Gen Z still dreams of influencing despite burnout and backlash What it really takes to walk away, reinvent yourself, and reclaim your identity Follow Lee Tilghman on Instagram @leefromamerica Grab a copy of If You Don’t Like This, I’ll Die Book Rec: Big Magic by Elizabeth Gilbert Follow Leigh Stein @leighstein Grab a copy of Self Care Book Rec: The Situation and The Story by Vivian Gornick

Oct 2, 2025 • 52min
Fighting Imposter Syndrome: Dr. Lisa Orbé-Austin
Do you have imposter syndrome? You’re not alone—70% of people will experience imposter syndrome at some point, and today, Dr. Lisa Orbé-Austin is here to help us break free. As a psychologist, imposter syndrome expert, and bestselling author of Own Your Greatness and Your Unstoppable Greatness, Dr. Orbé-Austin dives deep into how imposter syndrome shows up in our lives—and, most importantly, how we can overcome it. In this episode of Question Everything, she reveals: The subtle signs that imposter syndrome is creeping in The powerful link between self-worth and imposter syndrome Is there a link between imposter syndrome and perfectionism? How your upbringing shapes those feelings of self-doubt Are women especially vulnerable to imposter syndrome? Her personal experience battling imposter syndrome—even on the Today Show The two main cycles of imposter syndrome: overwork and self-sabotage How it impacts our personal lives and relationships Why marginalized groups are hit the hardest Simple steps to start loving yourself through it all Follow Dr. Lisa Orbé-Austin here Check out her latest book here Book Rec: The First 90 Days by Michael D. Watkins

Sep 25, 2025 • 58min
Hollywood’s Best Kept Secret Behind the Most Natural Faces: Holistic Plastic Surgeon Dr. Few
In a captivating discussion, Dr. Julius Few, a holistic plastic surgeon from Chicago, shares insights from over 30 years in aesthetics. His 'less is more' philosophy emphasizes the beauty of subtlety and why the best surgery is often invisible. He explains the dangers of filler overuse and the 'distortion vortex.' Dr. Few reveals his unique '85% rule,' the importance of turning patients away when necessary, and how his innovative procedures have transformed eyelid surgery. Tune in for a fresh perspective on beauty, aging, and self-acceptance.

Aug 21, 2025 • 55min
How To Stay Hopeful in a World on Fire: Mandana Dayani
When the world feels like it’s burning, some people retreat. Mandana Dayani builds. In this episode, Danielle sits down with the powerhouse behind I Am A Voter and Archewell, attorney, entrepreneur, and activist Mandana Dayani—a woman whose story spans war zones, boardrooms, and the front lines of cultural change. From escaping post-revolution Iran to advising the White House, launching viral civic movements, and leading Prince Harry and Meghan Markle’s media and philanthropic company Archwell, Mandana shares the moments that shaped her and the values that keep her grounded, outspoken, and unshakably hopeful. Mandana shares: The childhood escape from Iran that shaped everything The guilt that became her fuel Why she left a “perfect” persona behind to tell the truth What it really took to launch I Am A Voter + why she’ll never stop The heartbreak of October 7th and what it revealed about her community How she built Our Campus United and The OCU Chronicle in response to rising antisemitism Why integrity is her personal compass and the question she asks herself every night Her experience working with Meghan & Harry—and what storytelling means at scale The power of reinvention, especially when you're already at the top And why she believes optimism isn’t naive—it’s necessary Follow Mandana on Instagram @mandanadayaniBook Recommendation: The Way of Integrity by Martha Beck. Learn more about her work at www.mandanadayani.com

Aug 7, 2025 • 38min
The Raw Truth About Marriage, Motherhood + Wanting More: Valeria Lipovetsky
What happens after you build the life you always wanted? In Part 2 of this intimate conversation, Valeria Lipovetsky returns to open up about the messy, beautiful middle—marriage, motherhood, sex, ambition, and what it really takes to grow with your partner over time. She shares the honest truth behind her 12-year relationship, how becoming a mother in her early 20s shaped (and tested) her identity, and the quiet decisions that helped her rediscover herself—without blowing up her life. Valeria reveals: Why her marriage nearly broke under the weight of early parenting The new season she’s entering with her husband—and what changed Her personal “renaissance” and what it means to prioritize connection again Why she believes motherhood is the ultimate mirror The surprising (and hilarious) truth about sex after kids What she’s learned about boundaries, ambition, and giving yourself the big piece of chicken How she protects her peace while living a public life Plus, Danielle opens up about freezing her eggs, feeling like time is running out, and how a list of 1,000 questions (and a stranger's offhand comment) changed her life. This is part two of a two-part series. If you missed Part 1, go back and listen! Follow Valeria on Instagram @valerialipovetsky Book rec: A New Earth by Eckhart Tolle Grab the QUESTION EVERYTHING card game (updated edition)

Jul 31, 2025 • 42min
The Pressure to Be Everything: How Valeria Lipovetsky Created a Life That’s Fully Her
What does it take to build a life and career that’s fully, unapologetically yours? In this episode (part 1 of 2), Danielle sits down with entrepreneur and creator Valeria Lipovetsky for a conversation that’s less of an interview, and more of a mirror. They toss out the question cards, ditch the formal intros, and dive straight into the good stuff: ambition, motherhood, marriage, sex, social media, fertility, and the surprising superpower of asking better questions. Valeria shares: Why she never went to therapy—and what finally changed her mind The single moment that cracked open her authenticity Her unexpected (and poetic) obsession with secondhand shoes The timeline pressures no one tells women about—and what helped her reclaim her own The hardest season in her marriage—and how they’re finding their renaissance now Why her son taught her more about self-confidence than any book ever could Her honest take on growing a massive following while still feeling like she’s figuring it out The rules she broke to build a multi-million dollar business—and the one phrase that still haunts her from childhood This is part one of a two-part conversation—come back next week for even more. Follow Valeria on Instagram @valerialipovetsky Book rec: A New Earth by Eckhart Tolle Grab the QUESTION EVERYTHING card game (updated edition)

Jul 24, 2025 • 48min
What Mount Everest Taught Her About Failure, Fear, and Finding Her Voice: Alison Levine
What does it take to lead the first American women’s Everest expedition, survive a near-fatal heart condition, and keep climbing into your 50s? For mountaineer, author, and speaker Alison Levine it all comes down to one thing: putting one foot in front of the other, even when you’re terrified. Alison joins Danielle to talk about the summit attempt that made her the butt of a late-night punchline—and the second attempt that helped her rewrite what success really means. In this episode, she shares how a childhood marked by isolation, medical setbacks, and grit shaped her into one of the most inspiring leaders on and off the mountain. Alison shares: How being born with a hole in her heart shaped her risk tolerance The story behind the first American Women’s Everest Expedition—and why they had to turn around 270 feet from the top What it felt like to fail so publicly—and what she learned when she finally reached the summit 8 years later The mantra that replaced “go big or go home” Why fear can be your best asset Her surprising leadership advice (hint: ego isn't the enemy) The unspoken voice every woman battles—and how to train it to speak differently Why the strongest teams honor each other’s limits What she learned dragging a 150-pound sled across Antarctica Why she just left her successful speaking career to write a one-woman show—and what’s at stake How being “the smallest one on the team” became her greatest asset The quote from Pitbull that reframed how she views failure Book rec: Man’s Search for Meaning by Viktor Frankl Follow Alison on Instagram here.

Jul 17, 2025 • 1h 35min
Scooter Braun: “I Let It Burn”
Scooter Braun, a former music manager turned entrepreneur and investor, shares his transformative journey through 23 years at the top of the music industry. He reveals the vivid dream that prompted his walk away, discussing the real stories behind stars like Justin Bieber and Taylor Swift. Scooter candidly addresses the pressures of fame, his darkest moments, and how his divorce catalyzed personal growth. He also explores the future of music in a TikTok-driven world and offers insights into what it truly takes to spot talent.


