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Reclaiming with Monica Lewinsky

Anna Konkle

Reclaiming with Monica Lewinsky

Prufrock LLC

Self-improvement, Society & Culture, Education

4.81.4K Ratings

🗓️ 5 May 2026

⏱️ 64 minutes

🧾️ Download transcript

Summary

Emmy-nominated writer, actor, and co-creator of the critically acclaimed series PEN15, Anna Konkle joins Monica this week on Reclaiming for a conversation celebrating how dark humor can get you through almost anything. Anna retraces her path from a chaotic childhood to co-creating PEN15—a show that lets everyone process the tragicomedy of adolescence. She opens up about a five-year estrangement from her father that ended abruptly when she became his sole caregiver in his final months, and about the ways she’s been able to recategorize her mom—from a source of eye-rolling to a source of admiration. Anna reveals why now was the time to explore grief and reconciliation in her debut memoir, The Sane One, and how the solitary act of writing offered a different kind of healing than collaborative television. Expect a conversation brimming with laughter, warmth and tragicomic story swapping between Monica and Anna. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

When Maya and I pitched 1015, we were thinking it was quite funny in that we had all these

0:06.4

stories about being 13 that we weren't supposed to talk about. It's been funny for ages that

0:12.0

boys masturbate, but like, God forbid you did that as a girl. And the deeper we got into the writer's

0:18.1

room and everything that kind of got us excited and was like,

0:21.6

well, yeah, why can't we tell that story? Why does that feel wrong? And then the more we were like,

0:25.6

the patriarchy.

0:26.6

Yeah.

0:27.6

And then suddenly we were making like a feminist show. Hi, Anna. Welcome to Reclaiming.

0:43.0

Thank you. Thank you for having me.

0:45.0

Yes. I'm so excited because we get to talk about one of my most favorite things, dark humor.

0:50.6

Yes. And your new memoir, the same one. Yes. Yeah. And so you're like a multi-hyphenate as a writer, actor, showrunner, director, right? Yeah. Anything else? Did I. No, I think that's right. Do you play Mahjong? Not yet. Okay, you got to learn if you're in L.A. Do you play Mahjong? I do. I do. I do. I learned a couple years ago and my skill level is pretty much the same. Okay. I haven't gotten better. Okay, this is embarrassing? Is Mahjong the one where you press the, like, kind of like a disc? No. Oh, okay. That would, I think that's, no, I know. No, I was just. Is that air hockey? No, that's air hockey. There's one that's like, it's like a stick with like a that and then you're like pushing a disc. Okay. Is that you know what I'm talking about? No, it does matter. No, no, but maybe you've created a game that you and your mind. What does Mahjong look like?

1:44.4

Oh, well, okay, traditionally, traditionally it's sort of, they're kind of cream-colored tiles.

1:51.3

Okay.

1:51.5

And the ink on each tile is black, red, or green.

1:55.7

Okay.

1:56.2

But with this sort of Mahjong boom and Renaissance that has happened in the last couple years, they're now a million companies, and they make these gorgeous tiles that is half the reason I play. Because they're just so pretty. Okay, great. You know, it's like anything that can make you smile in today's world. Okay, I'm on that. I'm going to get on that. I like floral straws. Yeah, I know. I saw. I'm like, any of the things, right? All the things.

2:20.7

No, I know. Thank you. Wait, so I, we're going to talk about your memoir. I always feel like when someone comes on with a book that I always want to assure them that we're going to get to it. I'm going to talk about some other things.

2:31.4

No, no, but I, you know, because I've had that experience myself of where I just think, oh, no, oh, no, they, like, brought me on to do something else.

2:39.4

They're not going to talk about the thing that we're supposed to talk about, blah, blah, blah.

2:42.1

So, but I really, and I think in setting up the tone of your book, too, so much of you and how we know you is from Penn 15. And although I

2:56.2

want to say Pennis, but you know. You can. Yeah. Penis. Penis. Penice. Penice. And I feel like

3:04.9

you did such an extraordinary job of a creative way of taking us into our world of middle school.

...

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