Susan Orlean, JOYRIDE: A Memoir

Summary

Totally Booked with Zibby Owens

Guest: Susan Orlean
Episode: JOYRIDE: A Memoir
Date: October 30, 2025
Location: Live at the Whitney

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Episode Overview

This special live edition of "Totally Booked" features renowned journalist and bestselling author Susan Orlean discussing her debut memoir, JOYRIDE. Hosted by Zibby Owens, the conversation delves into the tapestry of Orlean’s professional adventures and personal life—detailing her storied career, turbulent romantic relationships, and resilience through societal upheavals. With Orlean’s signature candor and wit, the episode offers a revealing look at luck, heartbreak, starting over, disaster, and the ongoing mission of storytelling.

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Key Discussion Points & Insights

1. The Role of Luck and Perspective

[01:45–04:13]

• Orlean reflects on the powerful role of luck throughout her career and life but clarifies that while she acknowledges fortunate turns, her attitude shapes her narrative:
  • “I truly feel, especially in the course of looking back over my career and quite honestly, my personal life, that there are so many junctures where something really fortunate happened. ... Some of this is attitude, because I can also say I could look back at the course of my life and look at a lot of things and think, well, that didn't work out, or that wasn't successful or that was a disappointment. But I choose to see it all through the lens of this good fortune.” (Susan Orlean, 01:56)
• Orlean mentions her first national story for The Village Voice, which “happened” to run the week the publication shifted to color printing, giving her piece extra attention—a providential career boost.

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2. Writing as a Means of Making Sense

[25:56–27:15]

• Orlean reads a passage from her memoir, underlining her lifelong calling to writing:
  • “Writing is a job, but for me, it has always felt like a mission. I felt called, I really did, to describe ordinary life in a way that revealed its complexity and poetry, to show how rewarding it is to be open to and curious about the world and how much joy can be found in letting yourself be surprised... Writing was my effort to make sense of the human experience, of my experience.” (Zibby reading from Orlean, 25:56)
• Zibby notes how Orlean’s prose encourages empathy and a reexamination of seemingly ordinary stories.

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3. Grappling with a Difficult Marriage and Infidelity

[04:13–07:56]

• Orlean discusses the emotional aftermath of her ex-husband confessing an affair on the night of her book party, and how such traumas don’t always yield simple choices:
  • “Anyone who's had a difficult relationship…as I wrote it, I thought another person would look at this and very correctly say, what were you doing? Why'd you stay so long? That's crazy. But when you're in it, it's not so simple.” (Susan Orlean, 04:42)
  • “When you hurt people or people hurt you, it tends to have the effect of attaching you more…sometimes it's this impulse to say, I can fix it. I can make it. I'm gonna stay and make it better.” (Susan Orlean, 06:10)
• She reflects on the complexity of attachment, and how the reaction to betrayal can be “primal”—driven by connection rather than logic.

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4. Reinvention in Bhutan: A Fertility Pilgrimage and Younger Man

[07:56–14:10]

• Orlean narrates her journey to Bhutan, originating from a fertility-themed travel ad ("not necessary for you to have a baby"), which led to a whimsical and vulnerable chapter in her life:
  • “I just thought, I've gotta go on this trip. It just seems so funny that this was. You know, the proviso in the ad for the trip was that if you didn't wanna have a baby, you weren't required to get pregnant on the trip.” (Susan Orlean, 08:25)
• She embarks on a “holiday romance” with a much younger Bhutanese tour guide, reflecting with humor and honesty:
  • “I needed to make some new history for myself…I also felt like I don't want the last person that I slept with to be Peter. I want a new start in my new life as a person who isn't married to him.” (Susan Orlean, 12:43)
• Orlean describes the relationship as “insane, crazy, ridiculous but very sort of fun and full of good intention,” ultimately ending due to logistics and life moving forward.

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5. Love, 9/11, and a Postponed Wedding

[15:13–20:18]

• Susan recounts her romance with her now-husband, planned marriage, and being swept up in history as the 9/11 attacks forced her to postpone her wedding:
  • “My great concern at the time was my wedding gown was ivory and my shoes were white…And this was, you know, who knew? Like, that was. I woke up that morning thinking, am I gonna be able to get my shoes dyed in time for the wedding...And that morning, I'm just idly listening to the news and heard this strange report about a plane hitting the World Trade Center.” (Susan Orlean, 15:41)
  • “I called my parents…and I said to my mom, you know, look, we're gonna postpone the wedding...And my mom said, it's bad luck to postpone a wedding. It says it in the Talmud. And I said, mom, I don't think it says that in the Talmud... But the feeling that to undertake a joyful activity like a wedding would have felt so wrong.” (Susan Orlean, 16:41)
• The eventual wedding, months after September 11, becomes a moment of communal catharsis and celebration.

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6. The Trauma of California Wildfires

[20:18–25:56]

• Orlean describes the harrowing experience of evacuating her LA home during wildfires, drawing parallels to large-scale personal and collective loss:
  • “We spent five years lovingly restoring this mid-century modern house in the Hollywood Hills... And fire is very present as a—I think of it as like a wild animal that roams through LA at all times.”
• She details the immediacy and chaos of evacuation, the blanking of the mind in the face of trauma, and how little can ultimately be rescued:
  • “When it really happens, your mind goes blank. All I thought was, we need dog food, we need to get the dogs in the car and we need to get whatever medications we need. But as far as thinking about material things in the house, as I said in the book, everything was too much and not enough.” (Susan Orlean, 22:58)
• Orlean remarks on the increasing reality of climate disasters and their deep, lingering scars on families and communities.

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Notable Quotes & Memorable Moments

• "Luck has been my friend." (Susan Orlean, 04:00)
• "When you hurt people or people hurt you, it tends to have the effect of attaching you more." (Susan Orlean, 06:10)
• "I needed to make some new history for myself…I also felt like I don't want the last person that I slept with to be Peter." (Susan Orlean, 12:43)
• "Fire is very present as a—I think of it as like a wild animal that roams through LA at all times." (Susan Orlean, 20:42)
• "Writing is a job, but for me, it has always felt like a mission...to show how rewarding it is to be open to and curious about the world and how much joy can be found in letting yourself be surprised." (Orlean as read by Zibby, 25:56)

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Timestamps for Key Segments

• [01:45] Good fortune and the role of luck
• [04:13] Marriage, heartbreak, and attachment
• [07:56] Reinventing herself in Bhutan
• [15:13] Love story and the 9/11 wedding postponement
• [20:18] Experiencing California wildfires and evacuation
• [25:56] Orlean on writing, empathy, and her mission

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Tone & Takeaway

The conversation is candid, warm, and reflective—characterized by Orlean’s humor and willingness to examine both her triumphs and missteps. Listeners journey through milestone moments, both public and deeply private, witnessing how a storyteller finds meaning and connection amid unpredictability.

For readers and writers alike, Orlean’s journey in JOYRIDE (and this episode) is a testament to curiosity, resilience, and the enduring power of narrative.

Transcript

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[Zibby Owens]

Death, Sex and Money these are some of the hardest things for people to talk about, but on the award winning podcast, Death, Sex and Money host Anna Sale, writer and totally booked podcast guest, helps you realize how expansive stories around these three topics can be. Which is why I can't recommend the show enough. Produced by Slate, Death, Sex and Money dives into the big questions and difficult choices that are often left out of polite conversation. Not to mention, Anna interviews a range of guests, from famous names and experts to everyday people shining a light on the parts of life that can make us feel bewildered or alone, like motherhood and caretaking, addiction and so much more. So go ahead, follow and listen to Death, Sex and Money wherever you get your podcasts. Welcome to Totally Booked Live at the Whitney. I'm so excited to be in person in front of so many fabulous readers and also in front of so many fabulous authors. Now we get to talk to Susan Orlean, which is amazing. She's been on my podcast before, Back with Joyride, A memoir, her debut memoir here. Congratulations, Susan, and welcome.

[Susan Orlean]

Thank you.

[Zibby Owens]

Thank you. You say in the book that you have been drenched by the rain of good fortune. Tell us about that.

[Susan Orlean]

I truly feel, especially in the course of looking back over my career and quite honestly, my personal life, that there are so many junctures where something really fortunate happened. I'm not attributing my happiness in life purely to complete accident, but there have been a lot of instances where things just ended up falling kind of providentially in my direction. Some of this is attitude, because I can also say I could look back at the course of my life and look at a lot of things and think, well, that didn't work out, or that wasn't successful or that was a disappointment. But I choose to see it all through the lens of this good fortune. Some of it truly is good fortune. One of the things I mention in the book is the first story I did for a national publication was for the dearly departed Village Voice. It was my first story for a national Publication. And coincidentally, it was the first time the Village Voice ever used color. They only were in black and white. And then they made this huge leap forward and decided to, you know, start using color photos. The story that I wrote was the COVID story the week that they used color for the first time. So it got extra attention. So that's what I look at when I think, well, that was pure luck. That was just a matter of coincidence, of timing that, you know, turned out because more people noticed the story since it was such a novelty to see color in the Village Voice. But the bottom line is I'm really proud of the story, and the story got attention on its own merit. So I don't want to over attribute luck, but I do feel that luck has been my friend.

[Zibby Owens]

That's amazing. Well, the book really tracks your career and all the different assignments. Some you go into in great detail about who you were interviewing, but you also include a bunch about your own love life and your. We were like trench buddies, bonded by living through disaster together. We bought a new mattress, decided to have a baby. Felt the giddy rush of nearly drowning, but clawing to shore just in time, shocked by the glimpse of catastrophe. My gosh, you're such a good writer.

[Susan Orlean]

Just honestly, thank you. That was difficult thing to acknowledge. I think anyone who's had a difficult relationship, and certainly a lot of what I grapple with in the book is, as I wrote it, I thought another person would look at this and very correctly, say, what were you doing? Why'd you stay so long? That's crazy. But when you're in it, it's not so simple. Certainly in the case of having a catastrophic event like an affair, I don't think it's uncommon that if you. That you cling together in the midst of this very painful experience, that the only two people in the world who've had this is the two of you. So you're the two people who really understand what's going on. And I was very attached to Peter, very attached and certainly attached beyond where my logic led me. I think if I were a different person or if I'd been a little older when I met him, I might have been able to say more clearly, this is not fair, or this is, you know, he's got issues with me. Not to give anything away, but he told me about this affair the night of my book party. And, you know, at some point I said to him, even you've gotta admit that this is a little obvious, that you feel threatened or you're competitive or you Simply don't want me to be happy. It's not an accident. I mean, it was an affair that had been going on for a long time. Why that day? And I think when you hurt people or people hurt you, it tends to have the effect of attaching you more. And that's why when we look at people who are truly abused, you often have this very clinical reaction of saying, why did they stay? Why didn't they walk out the door? Well, humans are complicated. And sometimes it's this impulse to say, I can fix it. I can make it. I'm gonna stay and make it better. In my case, I think my attachment was sort of primal. I just felt very connected to him. And instead of saying, wait a minute, you're a complete jerk and you're trying to undermine me at a very happy moment of my life, one that I would have thought he would have enjoyed as well. And instead of saying, you know, I'll go it alone, I think I felt like grasping him closer. And I think infidelity also. I mean, there was an element of it that was competitive and where I thought, I'm gonna make him care about me more than this person that he cheated on. Cheated on me with.

[Zibby Owens]

And then you end up taking up with a guy from a younger man from Tibet. Is that right?

[Susan Orlean]

Bhutan.

[Zibby Owens]

Bhutan. I'm so sorry. Bhutan. And he was very far away.

[Susan Orlean]

Yes, far, far away.

[Zibby Owens]

And you tried to get him a visa and the whole thing.

[Susan Orlean]

Yes. Okay.

[Zibby Owens]

You didn't talk too much about him. Let's hear more about him.

[Susan Orlean]

Yes, well, I think that I did the. What is that? There's a book about so and so. Gets their groove back still. Yes.

[Zibby Owens]

Terry McMillan.

[Susan Orlean]

Well, I was sort of living that story, you know, after my marriage fell apart. And I was. I. You wanna put some daylight between yourself and this failed marriage, and it's not even. It's almost like you wanna begin creating new history that doesn't include the person who you've broken up with. I was actually. It's a very funny story with a weird irony. I had gone to Bhutan to do a story. I had seen an ad in a magazine for a fertility trip to Bhutan. Bhutan. Apparently, they're very devoted to the idea of fertility in the country. And you won't believe this, but the entire nation of Bhutan is decorated with paintings and sculptures of penises throughout the entire country. I kid you not. Like, you land in the airport, you get off the plane, and there's a giant painting. Merle mural of a penis, but it's seen as this celebration of fertility. And there's nothing kind of scandalous about it. It's just seen as, you know, we love fertility and we sort of worship the idea of procreation and so forth. So this was a trip to Bhutan from the US of people who wanted to attend some of the fertility festivals and go to the fertility sites in Bhutan. And in small writing at the bottom of the ad, it said, it's not necessary for you to have a baby. So I just thought, I've gotta go on this trip. It just seems so funny that this was. You know, the proviso in the ad for the trip was that if you didn't wanna have a baby, you weren't required to get pregnant on the trip. So I thought it was a really funny story. And Bhutan had almost no tourism at the time, so it was a very, very exotic place to go. They had 2,000 visitors a year total. So I went on the trip and I was really heartbroken. It was right after my husband and I had gotten separated and he had even considered coming on the trip, and then the last minute said no. So I went alone, and I was pretty vulnerable. I really enjoyed our tour guide. He was this adorable, much, much, much, much, much, much younger Bhutanese man. And so we began this sort of flirty relationship, which is probably not so uncommon on. And I was there alone with this tour group, and really everybody else was a couple because it was a fertility trip. And to my great astonishment, I ended up getting involved with this young man. And instead of thinking it was a holiday sort of romance, instead, I think it was entirely because I was in this very vulnerable state of having just gotten separated. I thought, we're gonna get married and we're gonna commute between New York and Bhutan. And I think I was just, like, out of my mind. And many of my friends here, because I did get him a visa and he came and stayed with me for a few months. And a lot of my friends thought Kay's really cute and he's charming, and this is insane. But I also think many of them understood that after a long marriage. I had been married to Peter for 16 years. I needed to make some new history for myself. I needed to feel. I mean, to be perfectly honest, I also felt like I don't want the last person that I slept with to be Peter. I want a new start in my new life as a person who isn't married to him. And it was an insane, crazy, ridiculous relationship, but very sort of fun and full of good intention. And when his Visa ran out and he went back to Bhutan. We said, oh, you know, we're gonna stay together forever. Even though I think we both knew perfectly well that it was ridiculous. And this was before zoom. This was before it was easy to stay in touch with someone on the other side of the world. Bhutan did not have the Internet. This was very, you know, was a country that was really in its own little bubble at that time. So it was, of course, impossible. And as luck would have it, soon thereafter, I got fixed up with someone who I fell in love with. And, you know, he was not very, very, very, very young. He was actually appropriately aged and lived not in New York, where I was living, but he lived in Boston. So it was not quite the same as New York. B.

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[Susan Orlean]

Hey there.

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Mia runs a pet grooming service in Chicago. But getting new clients was rough until.

[Zibby Owens]

I started using Acast.

[Susan Orlean]

I recorded my ad, targeted pet owners.

[Zibby Owens]

In the area and let Acast do the rest.

[Susan Orlean]

Now people all over the city know about my grooming services.

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[Susan Orlean]

A fresh cut, a friendly vibe, and a well placed podcast ad.

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[Zibby Owens]

And then because we're so rooting for you, like reading the book and finding out, like, going through as you tell the stories of your writing life, which, of course, is super, super interesting. Finding your ups and downs in love is also interesting. And then you finally fall in love and are getting married. And it turns out it's right at 9 11. That day was your wedding was that weekend. So you end up having to change everything again. Tell us about that.

[Susan Orlean]

Well, that was catastrophic on Tuesday of that week. My great concern at the time was my wedding gown was ivory and my shoes were white and I had to get my shoes dyed. And this was, you know, who knew? Like, that was. I woke up that morning thinking, am I gonna be able to get My shoes dyed in time for the wedding. We didn't even have our marriage license yet. We were very sort of sloppy and just said, well, we'll get it on Friday before the wedding, John was living in Boston, so we weren't even in the same city. And that morning, I'm just idly listening to the news and heard this strange report about a plane hitting the World Trade Center. And I called John, and he used to work on the 102nd floor. And he said, it must be a student pilot. That's the only thing that makes sense. In due time, we all learned to our horror what was going on. And my first reaction almost instantly was, we have to postpone the wedding. I just. Even without knowing how bad it was gonna be, I felt like there was an instant sense of catastrophe, of sorrow, of, you know, I remember going out really the next day and seeing those flyers all over New York, missing, another person missing. It was devastating. And you'll appreciate this. I call my parents and, you know, many of our guests were coming from out of town, and you couldn't come to New York. And I said to my mom, you know, look, we're gonna postpone the wedding. We can't have a wedding in this atmosphere. And my mom said, it's bad luck to postpone a wedding. It says it in the Talmud. And I said, mom, I don't think it says that in the Talmud. And if it does, I don't think it's specifically like, when there's a terrorist event that kills thousands of people, it's bad luck to cancel a wedding. And I think my parents were just. You know, they didn't live in New York. They didn't have the full sense of the heaviness of the atmosphere here. The feeling that to undertake a joyful activity like a wedding would have felt so wrong. I didn't have one minute of hesitation. I just thought. And the funny thing, of course, is the night before, on September 10th, I said to John, we were getting married in the Explorers Club. And I said to John, should we just pay the balance, you know, and just be done and send the money? He said, yeah, yeah, go ahead. It wasn't due, but I just thought, let's just pay it. So I go online and hit send and send the remainder of the money. And I thought, you know, my. I mean, we didn't know what was going to happen. We didn't know whether they would not agree to postpone the wedding. You know, nobody knew what was going on. And it was the lowest priority of concern but it certainly was a considerable expense that we thought, well, what's gonna happen? I'm so glad that we did it. I'm so glad. And maybe being not a young bride, not my first wedding, it was so easy to say, no, I'm not getting married in the middle of this heartbreaking. You know, the mood in New York for weeks and weeks and weeks was so, so heavy, so dark, so sad. When we finally got married at the end of November, everybody felt, I think, this sense that finally we can celebrate, finally we can. You know, many people said it was the first kind of happy celebratory occasion they'd been to since 9 11. And I was glad that it had that distance from the event and to give us a chance to celebrate in the fullness of the moment and not with the heaviness of what was going on.

[Zibby Owens]

And then towards the end of the book, actually at the very end of the book, you take us to la where you've left your house, stayed with a friend due to the fire, and are dealing with that as well. I feel like you've gone through just so many societal things. Tell us a little bit about that.

[Susan Orlean]

Really. Well, as you know, a horrifying experience. We spent five years lovingly restoring this mid century modern house in the Hollywood Hills. It's all wood, literally all wood. And fire is very present as a. I think of it as like a wild animal that roams through LA at all times. And not coincidentally, my last book, the library book, was all about fire. And so I wrote a lot about fire. And I had never lived anywhere where fire was so present. It's always on your mind, you're always conscious of it. You're always clearing brush from your yard. You're always aware of it. In a way that nowhere else I've ever lived has fire been as if it were part of the sort of ongoing scenery of the place. The day of the fires, the wind, I've never felt wind like that day. We thought our windows were gonna blow in. We never thought our. We just weren't thinking about the. We were thinking about our windows blowing in and we put tarps down through our house because we have a lot of very big windows. The fire began in the Palisades, began in Altadena. So we're sort of halfway between the Palisades and Altadena. So in part we felt like, well, we're far from both of those. Then all of a sudden a fire broke out in Runyon Canyon, which is right up the street from us. And everyone In LA has these alerts on their phone. And we went from green, meaning you're fine, stay at home, to yellow, get prepared. We thought, what? Wow, this is real now. And then red. Very quickly they said, you have to evacuate. It was a strange feeling because I've often thought, oh, if I had to evacuate, I would take this, I would take that. When it really happens, your mind goes blank. All I thought was, we need dog food, we need to get the dogs in the car and we need to get whatever medications we need. But as far as thinking about material things in the house, as I said in the book, everything was too much and not enough. Like, what was I gonna take? And also, we have a certain kind of advantage in the digital age that most of our pictures are digital. All my work is online, so whatever I was working on I could access even if my computer melted, even if my office burned down. But boy, was it terrifying. We drove down the hill to a friend's house and we were sort of settling in and we're all just glued to the television and glued to the watch duty app. And then they were told to get ready to evacuate because another fire broke out. It was so surreal, so strange. And the fire near them then got put out pretty quickly, but it was absolutely traumatizing. We probably had 13 friends who lost their houses both in Altadena and the Palisades, just lost everything. One friend who I checked, one of my colleagues from the New Yorker, I checked in with her in the beginning of the evening and she said, we're okay. And then her house burned down. And talk about the heaviness of 9, 11. Obviously it's different when it's a natural disaster versus someone choosing to harm you. But there was very much that feeling of despair, of heartache, of knowing how many people lost everything, feeling the vulnerability of the city. And that's just a reality. California. Well, listen, it's not just California. It's now become a state of being in a climate changed world. That fire, you know, Canada has become a victim of really terrible fires. And we don't care about it as much because it's another country, but you certainly get all the smoke. And there was a terrible story in the Times today about the number of people who are gonna die from wildfire smoke. Not to be so grim, but there was a lot of real heartbreak in the aftermath of the fire. And I think it remains, you know, I think LA still feels very wounded.

[Zibby Owens]

Well, sorry for going to all these dark places. Why don't I leave us with something a little bit more positive, which is your love of writing, which you write about so incredibly beautifully. And you also write about your parents and religion and there's just so much else. But let me just read this from the beginning. Writing is a job, but for me, it has always felt like a mission. I felt called, I really did, to describe ordinary life in a way that revealed its complexity and poetry, to show how rewarding it is to be open to and curious about the world and how much joy can be found in letting yourself be surprised. I wanted to draw readers in and convince them to appreciate these stories, especially ones they might not think they'd care about or find interesting. Perhaps they would begin to look at the world in a different way, one that was full of curiosity and welcome. I wanted to be a writer because I wanted to show that any life closely examined is complex and exceptional and can embody both the heroic and the plain. Writing was my effort to make sense of the human experience, of my experience. And I hoped that it might bring a reader to understand and maybe even empathize with a life or circumstance that initially might have seemed strange or impenetrable, which you have absolutely done. So thank you so, so much. Thank you.

[Susan Orlean]

Thank you so much.

[Zibby Owens]

Thank you for listening to Totally Booked with Zibi, formerly Moms don't have time to read books. If you loved the show, tell a friend, leave a review, follow me on Instagram Ippy Owens and spread the word. Thanks so much. Oh, and buy the books.

[Susan Orlean]

Ready to order? Yes.

[Zibby Owens]

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[Susan Orlean]

Everything.

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[Susan Orlean]

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[Zibby Owens]

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[Susan Orlean]

Ooh, tiramisu.

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[Susan Orlean]

Hey.

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