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.

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 <a href="https://www.iheart.com/podcast/1248-go-ask-ali-70320874/">Go Ask Ali</a>.

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.

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.

Now What? with Brooke Shields

Ali Wentworth turns the tables on BFF Brooke

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/d6b281d7-2cb8-494a-8406-af430149a54e/transcript

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