November 8, 2022 • 31 mins
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.
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:04):
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.
(00:27):
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?
(00:50):
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
(01:12):
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
(01:33):
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
(01:56):
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.
(02:18):
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.
(02:40):
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
(03:02):
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
(03:27):
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
(03:49):
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,
(04:12):
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
(04:32):
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
(04:54):
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
(05:15):
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,
(05:36):
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
(05:58):
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
(06:20):
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
(06:40):
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
(07:04):
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
(07:25):
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
(07:47):
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
(08:08):
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
(08:29):
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
(08:50):
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,
(09:13):
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
(09:36):
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
(09:59):
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
(10:20):
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,
(10:44):
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
(11:07):
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
(11:28):
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
(12:02):
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,
(12:23):
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.
(12:47):
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
(13:09):
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
(13:33):
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
(13:56):
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
(14:20):
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
(14:42):
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
(15:04):
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.
(15:26):
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,
(15:46):
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,
(16:08):
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
(16:28):
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
(16:49):
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
(17:11):
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
(17:32):
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
(17:55):
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
(18:16):
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
(18:39):
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
(19:00):
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.
(19:24):
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
(19:46):
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
(20:07):
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,
(20:29):
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
(20:49):
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,
(21:14):
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
(21:35):
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
(21:56):
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
(22:19):
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.
(22:41):
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.
(23:01):
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
(23:22):
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
(23:45):
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
(24:06):
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,
(24:27):
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
(24:50):
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
(25:11):
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
(25:33):
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.
(25:53):
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
(26:17):
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.
(26:41):
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
(27:03):
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
(27:24):
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
(27:46):
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
(28:08):
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
(28:30):
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
(28:53):
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.
(29:13):
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,
(29:36):
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
(29:58):
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
(30:18):
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.
(30:39):
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
(31:00):
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.
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.
(00:27):
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?
(00:50):
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
(01:12):
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
(01:33):
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
(01:56):
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.
(02:18):
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.
(02:40):
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
(03:02):
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
(03:27):
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
(03:49):
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,
(04:12):
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
(04:32):
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
(04:54):
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
(05:15):
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,
(05:36):
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
(05:58):
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
(06:20):
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
(06:40):
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
(07:04):
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
(07:25):
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
(07:47):
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
(08:08):
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
(08:29):
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
(08:50):
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,
(09:13):
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
(09:36):
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
(09:59):
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
(10:20):
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,
(10:44):
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
(11:07):
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
(11:28):
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
(12:02):
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,
(12:23):
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.
(12:47):
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
(13:09):
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
(13:33):
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
(13:56):
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
(14:20):
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
(14:42):
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
(15:04):
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.
(15:26):
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,
(15:46):
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,
(16:08):
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
(16:28):
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
(16:49):
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
(17:11):
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
(17:32):
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
(17:55):
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
(18:16):
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
(18:39):
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
(19:00):
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.
(19:24):
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
(19:46):
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
(20:07):
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,
(20:29):
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
(20:49):
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,
(21:14):
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
(21:35):
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
(21:56):
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
(22:19):
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.
(22:41):
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.
(23:01):
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
(23:22):
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
(23:45):
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
(24:06):
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,
(24:27):
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
(24:50):
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
(25:11):
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
(25:33):
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.
(25:53):
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
(26:17):
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.
(26:41):
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
(27:03):
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
(27:24):
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
(27:46):
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
(28:08):
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
(28:30):
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
(28:53):
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.
(29:13):
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,
(29:36):
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
(29:58):
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
(30:18):
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.
(30:39):
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
(31:00):
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.
Popular Podcasts
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations.
Death, Sex & Money
Anna Sale explores the big questions and hard choices that are often left out of polite conversation.
Stuff You Should Know
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.