What do you do in life doesn't go according to plan? That moment you lose the job, or a loved one, or even a piece of yourself. I'm Brookshields and this is now What, a podcast about pivotal moments as told by people who lived them. Each week, I sit down with a guest to talk about the times they were knocked off course and what they did to move forward.
Some stories are funny, others are cut wrenching, but all are unapologetically human and remind us that every success and every setback is accompanied by a choice, and that choice answers one question. Now, what do you sweat under your eyes? Is that? What? That is? Why? Under your eyes? I've never heard of anything like that. Almost supermodel, but I know so many supermodels. Nobody sweats under their eyes for the ones over eight. Um, there's something about the being
around me, being around you. It makes me nervous and then I start to sweat, and it it just um collects and it's part of my glasses and you'll see, you'll see a miss, you'll see the moisture. My guest today is one of my very best friends, Ali Wentworth. Ali is a comedian, writer and actor. A producer and a fellow podcast host. Her show, Go Ask Alli, drops each week and never ceases to make me smile, sometimes
cry a little. Ali's interviews are incredible, so good, in fact, that we decided to mix it up this week and have her interview me. We talk about our now what moments, our darkest, deepest secrets. We even play a few games, including her favorite bad choices. We had a blast and our producers enjoyed the conversation so much that they it run twice as long. Half of it airs today on this show. The other half airs this Thursday on Go Ask Ali. So, without further ado, here is Ali Wentworth.
Hello everybody, I am here with my bestie Ali, and Ali Wentworth is going to actually reverse the tables on us, and for a change, she's gonna put me in the hot seat this week. So Ali, should we just start? I think we should start. Been chomping at the bit. I'll wait to get down and dirty with you, all right. I'm gonna start off easy and then we're gonna go into some stuff that I hope nobody in your family
ever hears. But let's just carrying our listeners in slow and easy like jazz I'm gonna ask you just a very soft question, no curveballs. Do you remember when we first met? Not really, because so I made you were you were not that impressurable to me. No, I remember meeting you later. I remember in the when was I doing the show and you were dating a friend of Chris's. Did we ever meet? Then? Which show are you referring to?
Um my hit television show on NBC. I knew I had a bet that you would say suddenly, Susan within the first five minutes of your podcast. That's what I That's what I lead with. So I remember, we both have a house in Long Island, and we both have two girls that are basically the same age. So we were once at a stoplight in Long Island and I looked over and I saw you with these two little girls in the back of your car. I had two little girls in the back of my car, and I said,
this is ridiculous. I don't care if she's an icon. Our kids should play together, because you don't often find people that have kids the same age. So I rolled down my window and I said, motion for you to roll down your window, and you gave me that look like I can't can I just go to the market without fans A people who rolled down the windows for me, but they had bottles in their mouth. So and I said to you, hey, we have you know, daughters the same age. You know, we should do a do a
play date or something. And you gave me a very fake kind nod and then peeled off as soon as a light turned green. So well, I didn't recognize you. I didn't know you to recognize me. I just thought it was a mom to mom moment. But then I thought, and I turned to both my children in the backseat, and I said, celebrities are horrible people. Be friends with her, but um, that's so funny. You don't remember that. But
then we met later and we just immediately clicked. But then also, you were the first person that I went out on a limb and called you and said I want to work with you. I eat held me, I emailed you, and you said I love your show so much. It's a show that I created called Nightcap, and you said I would love to be on it. And I wrote a whole episode for you. And I had never reached out to anyone on my own behalf before. I always let agents do it. And all that, and so
I was like, I was like, cut, damn it. I want to work with this person, and what do I have to lose. I'm just going to ask her. And it was a big lesson for you. It's a huge lesson for me. Now you ask everybody for everything, No, but you've gotten. The one thing I said was please, I want to do this for you for myself, but I want you to challenge me. And you were fantastic. Thank you. But I think that it was in a way that was now what moment for me just because
I wasn't working. It was frustrated, and it was the first time I ever said, you know what, I'm not going to rely on agents or whatever, and I'm just gonna put myself out there. And I'm lucky that you responded the way you did. But I think it was a big, big lesson for me to sort of be humbled enough to say, I would love to do this if you have me, and if you'll trust me, Listen,
I'm a big believer in putting yourself out there. I was sitting in an office with a group of my agents a few years ago and I said, so, what what can we do? What's happening and they said, yeah, there's just really nothing out there for women your age. And I said, oh, have you told Diane Lane and Laura Linny that, because I think they're they seemed to be quite active. And they said, yeah, actress is in
your position. Yeah, there's nothing. There's really nothing. And I said, okay, thank you, and I walked out the door and I thought, I will not listen to that. Created they show nightcap from it. All right, So I know that you've asked some of your guests this, so I want to hear your take. How would you introduce yourself? Um, I would say I would start with I'm an actress. I would start with I'm Brooke Shields and I'm an actress and mother.
It's it those and I've just added entrepreneur because I've started my own company. I would probably say author as well, but not a model. You know what, I would not say a model. It's the weirdest thing because I was a model, but because it was sort of one dimensional, it didn't feel fully who I was. So when I think about it, the things that define me the most now are being an actress and being a mother. So growing up, are there people that you envied. I didn't
really learn envy until later. I mean I was obsessed with Renee Russo and I knew her in this uh seventies, and I went to school around the corner from where her apartment was, and my mom would let me before picking me up, I could go do my homework at her house. At her apartment older than you, right, she yeah she is. She was in her twenties, I think. And you go over and do your homework with an
older supermodel. Yeah, because my mom wouldn't. She didn't want me to stay at school and she couldn't pick me up until later, so Renee said come, no comment. She had like a low table and I would sit at her low coffee table and do my homework and she had bowls of walnuts that she had cracked like it was just she and I just looked. I thought she was the most beautiful creature I had ever seen. And what was she doing when you were doing homework? She
was just cracking walnuts. Yes, she was just cracking walnuts. Um. So she was kind of a babysitter. I mean kind of a babysitter, but really not. It wasn't too regular, but I remember doing that, and I just remember thinking she was so beautiful, and I was so impressed that she went to California to become a actor, so she was kind of a role model. I wouldn't say you envious of her. No, I didn't have envy, like I didn't till you met me. Yeah, that's when it really
kicked in. Um. Envy didn't really kick in until after college, when I wasn't getting any opportunity to act. Then it became fear based envy. You know, what is so and so doing what is so and so getting? You know, just pure insecurity, pure insecurity, I mean, and like I went to grade school with Laura Linney and she was sort of embarking and taking off on this thespian like she was really an actress. But you were going off
to model. So I'm just curious. How were your peers reacting to you going off and all of a sudden they're seeing you in commercials and magazines and on television doing Calvin kleinads. I mean, that must have been surreal for them. I mean, to hear her tell it, yes, you know, she said, there would be whispers of oh my god, this is what Brooks going to California to do a movie with Judge Burns, and you know, and
I didn't hear any of that. And when I came back, you know, we all picked up exactly where we left off. So it was sort of seamless in a weird way. Nobody bullied me, nobody was mean, nobody thought it was super cool. Whenever I had a photo shoot, my mom made sure that friends came, so I wasn't an isolated kid. I always had my actual friends from school around me. The most famous kid in my class was g Gordon Lyddy's son, who's one of the guys that broke into Watergates.
So I know what it's like to have somebody famous in your class and UM be envious of them, Yes, very envious. Yeah I wish I wish I didn't get into Watergate. Yeah I wish do you had to? Um? I never had do you have you ever had envy? Like as an actress, not as an actress. I never felt that somebody else had my career. Know, it always makes me laugh when somebody goes, you know, shelf I first stole my career. I'm like, UM, And I always felt like there was sort of room for everybody, So
there was never envy. I sort of thought, oh, well, she got to go do this movie. But I went to summer camp and I made friends with Kathy Horde Bay and you know, so it's like, yeah, that that's you know, I missed out on that, but I got
to do this. Yeah. And my husband, George Stephanopolis from Good Morning America's ABC, uh, he always said to me, you know, I remember I went to Network for the show Friends, me and Lisa Kudrow, and I always say, yeah, my life would have been really different had I gotten that part. He wouldn't have been married to me. And I go, that's true. I might have been married to Brad Pitt. But certainly happy with what happened. What's one really poor choice that you're happy you made as a
young person. I have thousands, but I'm wondering what yours is. I'm actually happy everything that happened, even the negative. I mean, I think that it was, in hindsight, a bit of a mistake for me to be so open about my virginity, because it never left me alone. And this was when you wrote a book about abstinence or that you were still a virgin. There was a section in a book
that I wrote when I was in college. Actually I ended up not penning it myself, and that was a huge mistake because the publisher didn't want what I wrote. I wrote a very sort of in depth first chapter, and they didn't want it that way. They wanted a simple, stupid book like I like leg warmers. And it was supposed to be what it's like to leave home for the first time and go to college and be on
your own. And the book was called on your Own, but in it there was one part of a chapter where I discuss not abstinence per se, but owning your choice if you don't feel comfortable. I would get a lot of fan mail from kids saying, Oh, my boyfriend's pressuring me and I don't want to have sex. What do I do. My narrative was you don't have to do anything you don't want to, But that was pulled
out of the book and became that became. I became talked about the most famous virgin in the world, and you would go on talk shows and have to range older men would ask you about your virginity, which was very creepy, Which was very creepy, and it was all but there was something to be in the line of fire at such a young age. In that way, I gained a resilience. It did sort of set me up to be ready kind of for anything in this industry, which can be difficult. So it begs the question, are
you still a virgin? Why had my kids buy IVF? So yeah, and I think even after you lost your virginity that was also in the news, Dean Kine. And then you more than made up for it after right, not nearly enough, but that's in a way waiting. I have regret around that because there was a sense of joy and freedom that I should have been able to feel within a relationship that was so lovely and so beautiful and sweet. Do you mean the privacy of it?
The privacy of it and the joy of it? I lost out Like that's something I try to tell my girls. How do you talk about sex with your girls? I do age appropriate lectures, and then I feeled questions. You know, I did tell them, there's no giving somebody your virginity. You're giving anybody anything. Taking the virginity the virginity is what makes me crazy. And so that's why when I think back to when you lost your virginity or gained
your sex, whatever it is. To Dean Kane, it just felt strangely put you know what I mean, Like, oh, I guess Dean Kane, who ironically became Superman, got brookshields virginity, Like what does that even mean? It's a surprise you wear a does he wear a pin? Yeah? He's try to change sort of how we talk about sex with girls. I mean, I found myself having conversations. You know, my girls just tell me everything. I mean, it's amazing, well
least one of them does. And that openness that we've established, you know, started with you know, I never was taught how to use the tampon. No, I mean, you know, was terrifying and torturous. And I we never talked about sex in my family. In fact, when I was in my twenties, I was helping my mother decorate a Christmas tree and I thought, you know, I'm twenty one. I'm going to ask my mother question. And I said, you know, mom,
how can we never talked about masturbation? And all of a sudden an ornament fell and I thought, oh my god, I've done it now, I've just imploded our relationship. And she turned to me and she goes, we never talked about masturbation because it's dirty and self indulgent. Okay, that's why I've never touched myself right there, thank you. So I made a choice when as a mother, to be
a lot more open about it. I'm surprised at myself in the way I'm mothering to my girls now, because I it's not a reaction to the way my mother was, but I'm so I'm okay with it for them, whereas I wasn't okay with it for yourself. Right, That's the difference that to me is so interesting. Yeah, alright, So this show is obviously called now what Now? Am I
saying it right? Or now what? Now what? Now? I'm curious what was your now what moment in your twenties and then what was your now what moment in your ties? I had a now what moment in my twenties when I I didn't get into a dance company and I had really, you know, tried very hard. I assumed I would make it, but it was so embarrassing to me to be a famous person right and go out for this, really put myself out there and not be good enough. And I just thought oh my god. Maybe it's true.
Maybe I don't. Maybe I don't. I'm not good. And that summer I took four and five dance classes a day and I got back in freshman week, I tried out for all of the different things again and I got into So, yeah, you have like a real workhorse sensibility. Okay, So this is a difference between us. You don't get into a dance company and you go, well, I'm just I'm gonna take five dance classes a day. I'm gonna
get better. I'm gonna study and work hard. If I didn't get into a dance company, I would go, well, that's fine, I'm going to start my own. We're not going to be as good stop my own, which is a very different way of now you know what I mean. But I sort of like your version better because what you're taking it into your own hands, whereas I'm still going to put myself in that position for them to pick me or not. But to answer this one, my in my thirties, my now what moment was when after
I VF, when I lost that first pregnancy. I had never felt such loss before, I had never felt such failure, and to have to lose the child to feel faulty. That was a very obliterating now what moment because I thought, oh, well, you've had a great life, you know you, but you don't deserve to do the most normal thing that So what did you do? Did you go to the supermarket and steal a baby? Yes? I went to the park and just took one. She had to. It was a twin.
What does she need to for? They look the same on our socialist world, we each we each get one. It really, it's really fair. Um. I thought, I'm gonna, I'm gonna. I'm gonna win if I'm gonna beat the system. And you did. I did. I ripped the estrogen patch off my body and bled and I was like, what when can I start? Next Wednesday? Next cycle? Ones? And it took seven more cycles. Wow? What was your now what moment? From your twenties? Um? I was living in
Los Angeles. I was in a comedy group called the Groundlings. I had come out one night with another actor and we were in a very dark parking lot discussing rehearsal schedules and we were attacked by a gang and the gang beat us up a little bit. They pushed me down on my hands in the back of the car, and they were lining up behind me and taking my pants off, and I ran out to the street screaming, and two of them chased me and didn't catch me.
I mean, that was pure adrenaline on my part. And I turned around and I saw my friend Mark being stabbed in the chest. But he was a Midwestern boys, so he had a jean jacket with that thick fleece the interior that caught the blades. And he ended up going to the hospital and he had surgery, and I ended up stopping people. The gang jumped in my car, which was like some beat up Volvo, and drove away. And I remember being at the hospital and thinking I'm
out of here, like I'm leaving Los Angeles. I'm going back to, you know, the comfort of my home. I want my mommy. And after a few days and a little bit of trauma therapy, and I realized, yes, this happened, this could have happened anywhere. I'm not going to run away from a life that I'm very consciously pursuing, you know, because of this, And so I stayed in Los Angeles.
Believe me, since that happened to me. I'm very aware of my surroundings at all times, but you know that was a moment where I could have just said this, this is too much, this is a sign, this is too much. Even my mother was like back east and I didn't do you think you had now what moments as a child? I had it now at moment probably every single day of my childhood. I mean I can tell you things like my parents were divorced when I
was one, but both my parents remarried. I would go see my father on the weekends and he was remarried, and she would tell me, I don't want you here. I can't believe I married somebody that already had kids. She would heat up a TV dinner and put me in front of Bob Newhart and Mary Tyler more. And so I had now at my mots of like, oh, I'm completely unloved, nobody wants me around. What am I going to do? I have an idea I'll perform. So my now what moments did turn into ambitions and how
can I change this? How can I make it better? So there's a lot of now what moments that were painful and hard, but there's a lot of now at moments, certainly my childhood that made me who I am today. So what was your thirties? One my now in the thirties was I had a boyfriend for eight years and we were engaged to be married, and he really he kept wanting me to set a date, set a date, and I realized, I don't think we should get married. We did not have a very physical sexual relationship. We
were kind of best friends. We played scrabble and watched Letterman. And I left the relationship and it was very, very scary for me, because you know, we had built a life together. I was more dependent on him emotionally and financially. And I left and sort of went into the abyss of not knowing can I pay my rent? Why did
you know you needed to leave? Because I knew that I couldn't marry somebody that I did not have a sexual relationship with, because people I knew that were married at that point said if you're not having sex now before you're married, forget it. And it just I knew it. I intuitively knew it. And I had to be alone for a while and sit in all the discomfort of where you depressed. Yeah, I was really depressed and I had a big now what now what? Now I'm an
actress and a writer with a very unreliable income. I'm living in a crappy apartment by myself. I'll probably never get married again. I'll probably never have kids again. And I had to really sit in a very scary place for a long time. And I ended up. I was work more. I wrote a bunch of movies. I finally afforded my first house, and I was I felt very resilient and independent. I had a lemon try and then I met my husband, George, and I had to sell my house in l A. I moved to New York.
But I did have an excellent amount of time where I was an independent woman. And I'll tell you, when you have that experience, you know, I'll always feel like, you know, God forbid something happens, I will be okay. I've proven it to myself. But that's a huge lesson to teach your girls. I can identify with that. When I divorced my first husband, I had been so absorbed into his world. His world was bigger than mine, it was richer than mine. I basically went from my mother
to his world and his control. You married a famous tennis player named Andrea Andrea, and I remember thinking, this is the most dangerous thing that you've you're ever going to do. But I asked myself the question, are you willing to be alone? And I knew I would rather be alone than continue under this umbrella, which by the way, was extremely safe, but you also got to hide behind somebody completely was famous and not have it be all
about you. And the thing is he Why he was right for me in the beginning was I felt safe. I felt really taken care of. I felt that I could be smaller. It wasn't all about Brookshields. He was such a huge, huge, famous, number one in the world. I mean everything around him was so big that I got to and you watch whenever we were walking. I was always staggered behind him a little bit, and I loved it. But then you became too small, so you had to get out of it. I became too small.
And also I knew it wasn't right because the physical part of the relationship was not there. I did not feel good about myself. I didn't feel celebrated physically, and having been a virgin forever and having had such a fraud relationship with sexuality, to have this kind of sort of platonic almost relationship. It was fine. It worked, and we had fun. We laughed, we we were like little
kids together. We sort of got to live a childhood in a weird way, like eating candy and you know, being irresponsible, and that doesn't sustain an adult relationship, that's the thing. And I knew that he would be a good father for someone else's children, but I was getting smaller and smaller and there wasn't room for both of us. And the extremes of living with someone I didn't know he was addicted to crystal meth then, but to live in such extremes with an addict, it was exhausting to me.
We had already done that your whole life with your mother, right, all right, I want to have a little fun, and I want to play a game called never Have I Ever, which I don't even I think you're gonna lose this because I think I don't, But um, we're gonna play Never Have I Ever? And then if you want to get more down and dirty, I'm going to play a game with you called Bad Choices on my podcast, which
will get even dirtier. So that's my little tease to go, Listen to go, ask Alli when Brooke and Eye play bad choices. But right now we're gonna play never have I ever? So I'm gonna ask you a question and you're gonna give me a pretty short answer. Okay, got it ready? You ever ghosted someone? I don't know what constitutes ghosting. You don't speak to somebody, you don't return
their emails or their texts. I don't think. I think I'm such a rule follower that I've always just in some way had the last word to say, like I'm just so sorry. I'm just you know, really busy and kind of put my give myself an out. All right, this is a good one. Have you ever had sex with a coworker? I have had sex with a coworker. Yes, who your husband, Chris hen She I've had sex with
Christmas when you were working together. Now, we weren't working together with the Christmas, the White House, Christmas, No, no, no, I was doing a movie. Oh did you have sex? I had sex with an actor in the co star. I mean it was an ensemble. Okay, you don't have to say Christoph Brackens. All right. Have you ever gone on a blind date? I have never gone on in a blind date. I can't go on. You can't go blind.
Although I went on a blind date with my husband, George Stephanopolis, and I knew exactly who he was, but he had no idea who I was, so it was blind for him but not for me. Yeah. Have you ever caught an ex cheating? Oh? God, God, I gotta get comfortable. This is going to be a three hour I did not walk in on an ex cheating, but I was dating an actor and he said he had to go to l A because his house was flooded, and three days later when I called him, we were engaged.
Three days later when I called him, a girl answered the phone. And then the inquirer called me and said that he had been seen at a restaurant with another actress. If we google this, will we get the names? Um, no, you don't have to say that. It's just it's just a fun Where's Waldo gave game? Yeah? He yeah, no, I was. The inquirer called me and and I was like, you better ask him, and I was just that's how
you found out that callow? All right? These were very rated PG questions and so I'm not that interesting that you are interesting, which is why on Go ask Ali We're going to play Bad Choices because we just crazed the surface of what kind of Shenanigan's you've been up with? You dirty hole? Um. Thank you for having me interview you. Thank you. This was a first for us to do it with the first for us. But you know what, I feel like I know you so well. I didn't
learn anything new you didn't know. That's why I think I want to play this game with you. I think I just I know you too much. You do know me too much. That was the amazing Ali Wentworth And if you want to hear more from her and hear us play the game Bad Choices, listen to her podcast Go Ask Ali this Thursday. Here's a preview. Do you think you would give the best lap dance in the room. You're gonna say yes, yes, because I worked really hard to be a good dancer when I was at Princeton. No,
you won't want to miss it now. What is produced by the wonderful Julia Weaver with help from Darby Masters. Our executive producer is Christina Everett. The show is mixed by Bahid Fraser and Christian Bowman. A special thanks to Nicki E. Tor and Will Pearson. If you liked this episode, please subscribe to the show on the I Heart Radio app, Apple podcasts, or wherever you get your shows.