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July 23, 2026 20 mins

Monica Lewinsky gets real about dating at 53 and the freedom of no longer giving a damn. She shares small but powerful ways she's found self-acceptance, and how she's learned to trust that she'll be fine, whether love shows up or not. Plus, the packing hack that will change your life.

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Speaker 1 (00:01):
You're listening to I Choose Me with Jenny Girl. Welcome
back to I Choose Me. Okay, I'm continuing my conversation
today with Monica Lewinsky, author, activist, and someone who has
shown us what it really looks like to rise, to
heal and to choose yourself. So let's get back into it.

Speaker 2 (00:26):
Now.

Speaker 3 (00:26):
With social media, we now have this whole new world. Right,
Like when you and I were going to school, you
couldn't be globally shamed.

Speaker 1 (00:37):
In this snow way instantly, Yeah, you just couldn't.

Speaker 3 (00:41):
It was like, you know, I remember this kid that
I had a crush on who was a year older
than me, and I wrote him a love letter and
he like showed all these kids at school.

Speaker 2 (00:50):
I was mortified. I was, you know, I was going
to die.

Speaker 3 (00:53):
And it's like, okay, but we're talking about the you know,
fifty kids who were at Hawthorne Elementary, you know, not
fifty million. Yeah, right, So it's.

Speaker 1 (01:06):
I mean the pressure, yeah, pressure that's on our young people, yeah,
and our older people because of social media, especially when
you're in that situation of you know being yeah, you know,
walk into your own beat or being a little different
than everybody else or whatever your differences are.

Speaker 3 (01:26):
Yeah, one of the things that I've really appreciated about
having a podcast is that the conversations I've had with
so many varied people, and the number of times that
you hear, you know, someone talk about a bullying experience
from when they were younger, and in fact, a whole

(01:47):
handful of people who've been on the podcast or friends
who participated. I've done a bunch of PSA campaigns for
Bullying Prevention Month, which is October, and one of the
ones we did was around this idea of reclaiming your name,
like you're not the worst name that you've ever been called.
And so a whole bunch of people generously gave their

(02:08):
time or voice or let us use their name and
with the name they were bullied with as a kid.
And it's pretty incredible to sort of see, we can
choose to not let that define us, right, and so
we get to take the power back from that.

Speaker 1 (02:30):
Do you think this is like a calling that you
stumbled upon? Like you know what I mean, Like I
think it is your universe made lemonade.

Speaker 4 (02:41):
Yeah, I think that it's a you know, maybe if
I live to an old age and on my deathbed,
I might see the expanse of my life differently.

Speaker 3 (02:56):
I think they're still I've had to fully accept I'm
a public person. There's something about my story that is
useful in the times we live in, and that's my life,
and so I need to accept that. And I just
I sort of feel like I'm just trying to do

(03:19):
the best I can with sort of what happened. Anyway,
it's amazing. Two, you've probably had this experience, especially you know,
when you were on book tour and stuff.

Speaker 2 (03:31):
I'm sure of.

Speaker 3 (03:33):
You get reflected back to you from people that you
don't know, ways that they ways that they like connect
with your story right and connect with your pain and
connect with your healing. And that's also not to I'm
not like trying to just push my podcast, but I
think that's the other Like, we're not prescriptive on the

(03:56):
I mean, you've been on it.

Speaker 2 (03:57):
We're not prescriptive.

Speaker 3 (03:58):
It's not tell me the three things that you did
to get through it. And this idea is it really
comes from my experience of how other people have reflected
back to me what I do, how that's impacted them.
And I found okay, people are actually even though I

(04:19):
love those. I click on those all the time on Instagram. Okay,
what are the four things to do.

Speaker 2 (04:26):
To find out exactly? I can't swipe fast enough.

Speaker 3 (04:29):
But I also think there's a real beauty in allowing
people that elasticity to find what they need in a story,
to find what they need where they're at, and.

Speaker 1 (04:41):
The strands that connect your story to their experience. And
it's so impactful. I know exactly what you mean. And
once you start hearing like the impact that you're you know,
having on other people and it's potentially helping them get
through a really dark time or situation, it fuels this

(05:02):
kind of like furnace of you wanting to keep doing
it because you're helping people, right, and that it's just
you reclaiming.

Speaker 2 (05:13):
Yeah, you're identity. And I think for me, given.

Speaker 3 (05:20):
Given both the negativity that I had coming at me
and the negativity of what happened to everybody involved, including
the country, you know, it's it. It's sort of it
gives it. It makes it easier for me to keep going.
Like they're you know, I don't always read comments on

(05:43):
things like I read the comments on the clips for
the podcast because I feel like it's important to know
what people are connecting right, and those conversations and sometimes
someone will just you know, tell me how something landed
with them in a way that was meaningful, and it's like,
oh my god, I needed to hear that so badly today.

(06:05):
It's such a gift when it becomes this reciprocal relationship.

Speaker 1 (06:11):
Yeah, because we don't talk to people in our lives.
You know, it's easy to go through a day and
not connect, yes, really connect with someone else instead of
just watching someone else's life for their great you know,
moments on Instagram or whatever. So having someone speak truthfully
and honestly about their own pain and suffering, it provides

(06:34):
them with that connection that they are missing so badly,
and it's really important. And I can see in you
the same thing I see in what I'm doing is
that when you help someone else, it helps ease your
own suffering because you need that connection too.

Speaker 2 (06:52):
Yeah.

Speaker 3 (06:53):
I don't know if you ever read Roxanne Gay's memoir
of her body Hunger, No, but I had read it
in I think twenty fifteen, and then I listened to
it recently and I was reminded of the more vulnerable

(07:13):
someone is, the more it connects with other people, and
the more you're helping ease other people's feelings of shame,
you know, because you're not alone, you know.

Speaker 1 (07:25):
And you're doing that. You're doing that with people that
listen to your podcast. You're also doing that with your guests.
I saw a clip of when Miley Miley was on
your show. I love her by the way.

Speaker 3 (07:42):
Oh my god, she's she is just she's everything, right,
She's everything you could imagine, and then more. She's just
wonderful and she's so funny. She's really funny.

Speaker 1 (07:56):
Well, he talked about feeling guilty about the effects of
her or fame have, you know, the effects that that
had on her family and her siblings, and you said
how you could relate.

Speaker 3 (08:07):
It's interesting because I think both Miley and I had
had these experiences, and it was amazing to see through
a younger generation that has not sort of sat in
shame around emotions for as long as our generation has.
She had done emdr around that and had moved past

(08:31):
it where I don't think I've even I've made peace
with some of it, but I think it lives in
me still in a way that it doesn't live in her.

Speaker 1 (08:43):
And that's interesting because I can yeah, I can totally
relate to both of you, and I think so many
people can, like when your circumstances or your situation detracts
or takes away something that is inherently someone else's sure
their life, their their name, you know, Yeah.

Speaker 2 (09:04):
I mean it's uh, it is.

Speaker 3 (09:08):
I'm so grateful that the last decade plus has changed
what people think when they hear my name the first
thing when they hear my name, and because I share
that last name with a lot of people, you know.

Speaker 2 (09:28):
And it's so I think that's you know.

Speaker 3 (09:32):
I executive produced this series on Hulu on Amanda Knox,
and one of the things that was Amanda is also
an EP And one of the things that was so
important to us and Hulu was so wonderful about was
letting us show the aftermath of what happens. You know,
most most of those shows would have ended Okay, she's exonerated,

(09:53):
let out of prison, Yay go home, end of shows,
you know, sentimental music. And it was so important to
us for people to try to get a window into
the collateral damage of what happens to people that it's
not just you, it's your family, it's your extended family.

(10:14):
You're impacted by how you move through the world by
you know, and so that I think is important because
we tend to you know, it's the image that comes
up is the sort of the arena, the gladiator arenas
of old, you know, and that it feels like we

(10:38):
have that one person in the center that we're throwing
you know, horrible things out and yelling or cheering for
and we.

Speaker 2 (10:50):
Don't see them go home.

Speaker 3 (10:51):
We don't know that maybe their mom or dad is
sitting in the stands rooting for them or worried about them,
like we just don't, and so they become entertained in
a way. And I think it's important for us to
how we hopefully shift consciousness and shift society for those
things to seep.

Speaker 1 (11:12):
In, you know, right, I think just acceptance people. That's
I mean, oh, it's so hard though, so hard when
people say, Monica Lewinsky, now, what do you hope comes
to mind?

Speaker 3 (11:27):
I mean, I think if at the end of my
life I was a poster child for surviving shame and
being able to move on and work to create your
own ending, You're chosen ending or you know, my production
company is called All the Endings, and it's like you
know that there's that It's not we're not faded that way.

(11:51):
Certain things in life are faded, but I think we
can we can move the needle on those things.

Speaker 2 (11:58):
And that is important because.

Speaker 3 (12:02):
We go through these kinds of humiliations or losses, you know,
and everything in between all the time in life. If
you're living, if you're if you're out there living, you're
going to you're going to be disappointed sometimes, You're going
to lose. Sometimes, you're going to be rejected sometimes, and

(12:24):
you know, the ability to pick ourselves back up.

Speaker 2 (12:27):
I have a friend.

Speaker 3 (12:27):
I think it maybe comes from the twelve step program
of progress not perfection, and that is such a great
you know, it's such a great thing.

Speaker 1 (12:37):
So do you have a lot of supportive girlfriends?

Speaker 2 (12:40):
Oh, I'm very lucky.

Speaker 3 (12:42):
I have my like my inner circle, you know, I
have my Okay, these are my people. I'm not afraid
to say the good, I'm not afraid to say the bad.

Speaker 2 (12:53):
And with new.

Speaker 3 (12:54):
People, I think there's this I think I have a
relationship with my intuition and where I don't know if
it's good or bad. I mean, I'm going to say
I think it's good. It would be pretty hard to
move through the world just bitter and mistrusting everyone that
I have an open heart. I am trusting, and so

(13:14):
I think that it's I'm more trusting than I might
expect of someone. But boy, if my spidy senses go up,
I like really shut down to a point where I
started to get a little paranoid about you know, I'm
just sort.

Speaker 1 (13:30):
Of whoa, whoa.

Speaker 3 (13:33):
Yeah, and and sometimes still I don't listen to those
warning signs, you know, and and you know, but yeah,
I'm very I have I'm very lucky with my friends.
I have a box sitting on my counter that my
best friend from college sent me.

Speaker 2 (13:54):
She's like, I've collected these things for you. So it's
you know, it's not even for my birthday.

Speaker 1 (13:59):
So which is up by the way, Yes, how are
you celebrating.

Speaker 3 (14:03):
I am going to be on vacation that week. That's
like one week of vacation this year and perfect.

Speaker 2 (14:10):
Yeah.

Speaker 3 (14:11):
So I think we're doing with friends that I was
with last year and we all play majong together and so.

Speaker 1 (14:18):
It was amazing.

Speaker 3 (14:19):
Yeah, they got a cabana on the beach and we
played mashong all day on the beach. So I think
we're doing that the day before my birthday and on
my birthday going to an event of a friend of
ours company.

Speaker 1 (14:34):
So it must be difficult. Any woman I talked to
says dating is difficult, especially at our age.

Speaker 2 (14:49):
What is it like for you? Are you dating?

Speaker 1 (14:54):
Do you ever want to date? I?

Speaker 2 (14:56):
Yes, I date.

Speaker 3 (14:58):
I think this year it's been a little less than
the last year because I just had been juggling a
lot more professionally than I expected to be, and I've
gone on dates with some amazing men, and you know,
but I am a little more sensitive to certain things,

(15:22):
and it's sometimes it's hard. It's it could be really
hard to tell the difference between nervousness, like someone else's nervousness,
and feeling like you need to hold the space for
someone else because they're more nervous because they're not a
public person and you're a public person.

Speaker 2 (15:40):
And so there's sort.

Speaker 3 (15:41):
Of that dance and even you know, the times where
they're trying to make you feel comfortable, it sometimes is
a miss, you know, and it's the but you know,
I think again back to the.

Speaker 2 (15:57):
Acceptance and my.

Speaker 3 (16:00):
My sister in law's turning fifty, and I was like,
it's the best decade.

Speaker 2 (16:04):
She's like, really and nicely.

Speaker 1 (16:05):
Yes, because you just it is.

Speaker 3 (16:10):
You're baked, Like all right, all the fucks are kind
of gone, so yeah, I take it, leave it.

Speaker 2 (16:17):
Yeah. So I do feel like.

Speaker 3 (16:21):
Something that evolved for me in the last several years
was this, you know, Okay, I might not this lifetime,
I may not end up with the person at some point.
You know, it just may not have happened for me,
and I'll be okay, and if it does have, like,
I be equally surprised.

Speaker 2 (16:43):
If it doesn't happen, or.

Speaker 1 (16:44):
It does happen, that's a perfect place to land because
that's again acceptance of what is, instead of fretting over
it or trying to force something or feeling badly that
it's not a certain way, giving into societal pressures. Yeah,
I love that. That shows just like immense strength and
growth in you. Yes, you know, and once you're like,

(17:06):
I'm fine on my own, then let you know, I'd
be surprised if something doesn't just fall into place for you.
We'll see, you know, when you're least expecting it.

Speaker 2 (17:17):
Yeah.

Speaker 3 (17:18):
Yeah, it's but you know, I always joke when people
say that, I'm like, okay, now show me how to
least expect it right. So I know it's hard, it's tricky,
but you're doing a great job.

Speaker 1 (17:31):
I have one last question for you. Yeah, Monica Lewinsky,
what was your last I Choose me moment?

Speaker 3 (17:39):
One of my friends was offering to We had talked
about like doing something for my birthday, so before my birthday,
but because I won't be in La and this and that,
and I have a lot going on. It's supposed to
be Sunday, and I have a lot going on this week,
and I'm on the one hand and I want to receive,

(18:02):
I'm trying to be a better receiver, and on the
other hand, there's just some stressful stuff going.

Speaker 2 (18:08):
On this week.

Speaker 3 (18:09):
And so I said, I think I'd probably rather not.

Speaker 2 (18:14):
You know.

Speaker 3 (18:15):
I think what I was able to do was to
sort of think about, yes, I might just feel joy,
or it may feel really performative to me, and the
energy of being performative is something I need to put elsewhere.

Speaker 2 (18:29):
And so that sort of feels like a choose me.

Speaker 1 (18:32):
What are you going to do on Sunday instead?

Speaker 2 (18:34):
Oh? Probably pack?

Speaker 1 (18:37):
Just relax. Your pack is so stressful.

Speaker 2 (18:40):
It's so stressful, you know.

Speaker 1 (18:42):
My favorite thing to do.

Speaker 2 (18:43):
I know what.

Speaker 3 (18:45):
My small hack, although I never give it to fitting
it away after, which is annoying, is I pull out
a rack I put you know, I put together one
of those temporary clothing hanging racks. And then that way
I feel like, Okay, I'm you got your outfits right,
especially because I'm going to be doing a bunch of

(19:06):
podcast interviews on this trip, and so it's like, okay,
you know what mood am I going to be in?

Speaker 2 (19:13):
You know?

Speaker 3 (19:13):
You just and then but I recently, I'm going to
brag for a minute. I went to the TED conference,
which is like five or six days in April, and
I took a carry on only.

Speaker 2 (19:26):
Which is like beyond for me.

Speaker 1 (19:29):
I love that you're bragging about being in a carry on. Yeah,
it makes a big difference, especially when you don't have
somebody to help you slip exactly exactly.

Speaker 2 (19:39):
But I tried that. Have you seen that thing on Instagram?

Speaker 3 (19:41):
It's the Sudoku method of packing with the cubes?

Speaker 2 (19:46):
No, it's no, It's like, what is it?

Speaker 3 (19:49):
Three outer layers, three bottoms, and three tops and you
sort of have them and you and you just sort
of choose the color palette and then you mix and
match everything and it worked.

Speaker 2 (20:03):
Okay, yeah, I'm going to google that. I'll send it
to you.

Speaker 3 (20:06):
Actually, I send you to post it and I.

Speaker 2 (20:09):
Was like, oh, thank god, you've found to you I know.

Speaker 3 (20:11):
So I'm going to text you right after this and
I will when I find the sudoku thing.

Speaker 2 (20:15):
I will look at to you.

Speaker 1 (20:16):
Oh my god, You'll make my life so much better
because I hate packing.

Speaker 2 (20:20):
Yeah, me too.

Speaker 1 (20:21):
Well, I wish you a much better week next week.

Speaker 2 (20:24):
Thank you.

Speaker 1 (20:25):
And I know that all good things are coming for
you because you are looking for them. And I'm just
really happy for you.

Speaker 2 (20:32):
Thank you. Thank you for having me so lovely.

Speaker 1 (20:36):
Thank you for being here.
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Jennie Garth

Jennie Garth

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