Gayle King (CBS Mornings, Oprah Daily) and Brooke talk about the difficulties of divorce, the biggest co-parenting challenges, and the one unforgettable piece of advice Maya Angelou gave Gayle when things got tough. Plus, Gayle reflects on working at CBS during the height of the #MeToo movement and shares a "now what" moment from her childhood that has come to define her life.See omnystudio.com/listener for privacy information.

New York Times bestselling author Celeste Ng (Little Fires Everywhere, Everything I Never Told You) chats with Brooke about the underlying meaning of her latest novel Our Missing Hearts, why she doesn't take public reaction to her work personally, and what it's like to take a back seat when a project gets adapted by Hollywood A-listers. Plus, Celeste reveals how a harrowing racist encounter from her childhood has forever changed the way she approaches injustices in the world. See omnystudio.com/listener for privacy information.

Actor, comedian, and Brooke’s bestie Ali Wentworth joins the show for our first-ever crossover episode! Brooke shares why she regrets waiting to lose her virginity, Ali reveals the time she asked her mom about masturbation on Christmas, and the two swap stories about their failed relationships (from ending an engagement to catching a cheating ex-fiancée). Plus, Brooke reveals if she's ever slept with a coworker during a fun game of "Never Have I Ever." The party continues Thursday with a down-and-dirty game of Bad Choices on Ali’s podcast Go Ask Ali.See omnystudio.com/listener for privacy information.

Brooke talks with Patton Oswalt (The King of Queens, The Goldbergs, A.P. Bio, I Love My Dad) about the “coin flip” that landed him in San Francisco, how grief made him more emphatic after the tragic loss of his first wife Michelle, and what he wishes internet trolls understood about his friendship with Dave Chappelle. Oh yeah, and Brooke tells us about the time she sent her mom into the afterlife without pants.See omnystudio.com/listener for privacy information.

Kal Penn (House, Designated Survivor, Harold & Kumar Go to White Castle) opens up to Brooke about his “tragic” rejection from Yale, being pigeonholed in Hollywood because of the color of his skin, and how Harold and Kumar helped him subvert racial stereotypes and land his dream role. Then, Kal digs into the biggest pivot of his life: his decision to leave acting to go work for the Obama Administration.See omnystudio.com/listener for privacy information.

Geena Davis (Thelma and Louise, A League of Their Own, Commander in Chief) joins Brooke to talk about the perils of having polite parents, how playing empowered female characters onscreen helped her cope with childhood trauma and her latest thoughts on Bill Murray. Plus, she shares a #MeToo moment involving a Hollywood director that changed how she forever saw the industry.See omnystudio.com/listener for privacy information.

Brooke and Julianna Margulies (ER, The Good Wife, The Morning Show) swap stories about their bohemian childhoods, what it’s like to realize you’re famous, and how they've learned to shed the labels given to them by others. Plus, why Julianna turned down a $27 million paycheck in order to leave ER and how she dealt with the unexpected backlash from fans.See omnystudio.com/listener for privacy information.

What do you do when you encounter the unexpected? That make-or-break moment that leaves you crying in front of strangers or quitting your job to pursue your true passion. Now What? with Brooke Shields dives deep into the world of redos, resets, and forward fails: From career pivots and personal missteps to moving through grief (or just plain moving on). Join Brooke as she sits down with authors, experts, and celebrity guests to hear their ‘now what?’ moments and learn what they’ve done (or are still doing) to get through it.See omnystudio.com/listener for privacy information.