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.

Ali Wentworth turns the tables on BFF Brooke

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.

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Legendary broadcast journalist Katie Couric joins our final episode to share lessons she's learned from her extraordinary career. Katie tells Brooke how she responded when CNN’s president questioned her talent, what she took from her history-making turn at CBS Evening News, and how she fought to shake the “morning news albatross.” Speaking candidly about the lingering pain from her husband and sister’s deaths, Katie also shares how standing up to cancer has become her life’s mission. See omnystudio.com/listener for privacy information.

Katie Couric on shaking the morning show stigma

Brooke’s hubby Chris Henchy makes his “Now What?” debut! The couple swap details about their meet-cute on the Warner Brothers lot, their parenting skills and favorite family traditions, and how Chris’ dedication to his Irish granny helped convince Brooke he was "the one." Chris also opens up about his journey from finance bro to comedy writer, and shares how he moved on from the failure of his first movie to one of his greatest successes to date. See omnystudio.com/listener for privacy information.

Brooke's husband Chris Henchy takes the hot seat

Writer, director, and actress Jennifer Esposito stops by to talk about her critically acclaimed new film, Fresh Kills, and shares how making her dream project helped her heal from years of abuse from industry heavyweights. Brooke and Jennifer discuss the importance of self-advocacy, Jennifer’s life-long struggle with celiac disease, and the power of art to breed greater empathy and understanding. See omnystudio.com/listener for privacy information.

Jennifer Esposito on not taking no for an answer

Author, advice columnist, and all-around badass Cheryl Strayed joins Brooke for a wide-ranging conversation about parenting, childhood poverty, and what it means to be rich in love. Cheryl gets candid about the years leading up to her famous trek on the Pacific Crest Trail, and shares why she’s in need of another life-changing journey. Plus, the one thing Cheryl keeps in mind whenever she gives advice. See omnystudio.com/listener for privacy information.

Cheryl Strayed on embracing the gray area

Neurosurgeon, podcast host, and CNN’s Chief Medical Correspondent Dr. Sanjay Gupta chats with Brooke about why some brains respond more positively to “now what” moments than others, what his mom’s refugee journey taught him about resilience, and why his pivot into broadcasting was one of the biggest challenges of his life. Plus, Brooke and Sanjay share the advice they’d give their 25-year-old selves. See omnystudio.com/listener for privacy information.

Ali Wentworth turns the tables on BFF Brooke

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