Now What? with Brooke Shields

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Ali Wentworth turns the tables on BFF Brooke

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.

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  Katie Couric on shaking the morning show stigma

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  Brooke's husband Chris Henchy takes the hot seat

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  Jennifer Esposito on not taking no for an answer

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  Cheryl Strayed on embracing the gray area

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  Dr. Sanjay Gupta on training your brain to be resilient

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  Joan Baez on learning to confront the past

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  Cedric the Entertainer on putting fatherhood ahead of fame

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  John Stamos on sobriety and choosing to survive

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  How Sarah Silverman changed comedy’s boy’s club

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  Why Willie Geist is the anti-Anchorman

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  Bowen Yang on why he ditched a medical career for comedy

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  Erin Andrews on refusing to give up hope

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  How being a benchwarmer pushed Ellie Kemper into comedy

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  Now what do we do about women’s health?

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  Savannah Guthrie on why a little fear is a good thing

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  Michael Strahan on the importance of being seen