I Am Not Your Enemy with Whistleblower Reality Winner

Summary

Dear Chelsea – “I Am Not Your Enemy with Whistleblower Reality Winner”

Originally aired: September 18, 2025 | Host: Chelsea Handler | Guest: Reality Winner

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Episode Overview

This episode of Dear Chelsea features a profound and candid conversation between Chelsea Handler and Reality Winner, the former NSA contractor who became a whistleblower by leaking classified information about Russian interference in the 2016 U.S. election. The episode explores Winner’s journey from the Air Force to prison, her motivations, the personal consequences she faced, and her ongoing process of rebuilding and searching for healing and purpose. Chelsea provides context for Reality’s story—including recent film and book adaptations—before delving into a wide-ranging discussion about justice, trauma, redemption, and what it means to fight for your convictions.

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Main Discussion Points & Insights

1. Reality Winner’s Background and the Leak

• Early Career
  • Served as an Air Force linguist and intelligence analyst, then took a contract position with the NSA primarily to maintain her security clearance.
  • Her role offered little meaningful work: “There was nothing for me to do. I just sat there and watched YouTube all day ... They didn’t really know I was there.” (11:15)
• The Leak
  • Winner felt compelled to leak a classified document revealing Russian interference in the 2016 election, believing the public deserved the truth.
  • She describes her motivation as a sense of right and wrong, not naivete: “I really just had a sense of right and wrong and that you wanted to share. And I think that’s very admirable.” – Chelsea Handler (12:18)
  • Winner clarifies: “I didn’t even really consider the consequences ... It was very clear that I did what I did for the greater good.” (12:50)

2. Knowledge Gaps and Whistleblower Precedents

• Despite knowing names like Edward Snowden and Chelsea Manning, Winner was kept ignorant of their cases and possible legal consequences due to strict NSA regulations:
  • “We were kept in the dark...you could be charged with the Espionage Act just for reading certain articles ... I didn’t know what they had gone through. I was just kind of acting in the dark at that point.” (13:16)

3. The Role of The Intercept and Her Arrest

• The Intercept, the outlet she leaked to, made errors that exposed her identity, a problem with a pattern:

  • “It was not a mistake. It was on purpose. There were three of us in a very short succession that were outed by their incompetence, but then championed by them. So they would create victims and martyrs and then try to be the only media outlet fairly reporting on them.” (15:39)

• Arrest & Interrogation

  • FBI arrived at her house, heavily armed, and Winner was deeply anxious about the safety of her pets and herself:
  • “11 men ... all of them were armed ... they kept leaving my doors open and interacting with a dog that had previously been extremely aggressive...” (16:25)
  • She highlights the unique fear and powerlessness when facing armed federal agents:
  • “If my cat had gotten out ... would they shoot me in the back? ... They have the only control of the narrative.” (17:15)

4. Legal Process and Mental Health Struggles

• Remained in jail for a year without bail, then sentenced to five years in prison.
• Admits to deep psychological distress:
  • “I started planning and doing dry runs of my suicide ... The last piece of the puzzle was...make sure my mother wouldn’t be home when she got the news.” (22:20)
  • Eating disorder (bulimia) worsened—her legal team adjusted visitation to accommodate her needs: “They started initiating that type of care ... It made enough of a difference to get me through the winter of 2017.” (24:59–26:07)

5. Life in Prison and Adjustment After Release

• Made friends in prison, some of whom she still keeps in touch with:

  • “I went and ran a half marathon with one of my friends, Stephanie ... She’s doing so well.” (33:31)

• The release process was fraught with anxiety, constant surveillance, and strict rules:

  • “I was constantly under so much pressure from the top down ... the only way the pressure could come out was sideways. And so my family were...in my line of fire since I couldn’t do anything to ease the government pressure off of me.” (34:08)

• Early Post-Prison Life

  • Quick, misguided marriage during her re-entry period, struggles with bonds and boundaries—seen as “inmate thinking patterns”:
    • “The way you think and operate as an inmate is, you find what you want and you find a way to secure it ... So I married him secretly.” (40:53)

6. Recovery, Healing, and Looking Forward

• Now immerses herself in animal rescue and coaching CrossFit—a crucial part of her road to recovery:
  • “I’m just Coach Re, I’ve been coaching CrossFit now for four years ... It’s a cult. But it’s also what keeps me from being bulimic.” (44:22)
• Studies veterinary technology, seeks anonymity in her hometown, and focuses on building a future.

7. Lasting Impact, Social Justice, and Caution

• Winner’s experience radicalized her understanding of the US criminal justice system:
  • “What is happening to millions of other Americans can happen to you at any time ... All of us are one interaction with law enforcement away from being in solitary confinement without legal justification.” (46:43)
• She expresses both gratitude and brittleness—her worldview is forever changed, more cautious and realistic:
  • “I don’t necessarily feel stronger. I do feel a little bit more brittle.... I know what can take me down really quickly.” (46:43)

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Notable Quotes & Memorable Moments

• On Motivation to Leak:

  • “If the American people had the information on that document ... it would answer a question that was burning a hole in our society in 2017.” – Reality Winner (14:18)

• On PTSD and Therapy:

  • “Therapy and me don’t get along well ... For three years of probation I was court-ordered to do it ... But I have been able to get my veterans benefits back up and running. So I was properly diagnosed last fall and have been doing a lot better with my mental health.” – Reality Winner (53:02 & 53:24)

• On Prison Transformation:

  • “I didn’t know how to relate because the things that I thought were funny were so inappropriate all the time, which was fine. But I don’t think anybody gave me or my family the vocabulary to talk through decompressing a huge trauma.” – Reality Winner (34:08)

• On Post-Whistleblower Life:

  • “Honestly, I just want to know that my community is a better place because I’m in it. ... My view of the world has gotten a lot smaller with this criminal conviction.” – Reality Winner (48:56)

• On Social Justice Realization:

  • “All of us are one interaction with law enforcement away from being in solitary confinement without legal justification ... My basic understanding was, yeah, if they charge you with a crime, they can do anything to you after that. And now they don’t even have to charge you.” – Reality Winner (46:43–48:44)

• Chelsea’s Encouragement:

  • “You went through hell and you’re still here to talk about it. And that in and of itself just shows you have a purpose.” – Chelsea Handler (61:45)

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Key Timestamps

• Background & Introduction – 04:44–07:59
• Reality Winner on Her Experiences – 08:01–14:13
• The Leak, The Intercept, and Arrest – 15:02–17:16
• Life in Jail/Prison: Suicidality & Eating Disorder – 21:39–26:07
• Life in Prison / Release / Early Struggles – 33:26–40:53
• Rebuilding and Family, Divorce / Healing – 41:37–44:22
• Animal Rescue, CrossFit as Recovery – 44:22–45:31
• Lessons Learned, Social Justice, the Current Climate – 46:43–60:25
• Moving On and Final Thoughts – 62:14–62:46

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Episode Takeaways

• Intimate look at the internal and external costs of whistleblowing, often omitted from national conversations.
• Candid exploration of prison and probation’s psychological impacts, especially for someone motivated by conscience over profit or politics.
• Deep critique of media handling of whistleblowers, the justice system, and US security culture.
• Message of resilience, humility, and the importance of peer and family support structures in surviving trauma.

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Chelsea Handler’s closing thought:
“You’re a survivor ... and that in and of itself just shows that you have a purpose.” (61:45)

Reality Winner's hope:
“Honestly, I just want to know that my community is a better place because I’m in it.” (48:56)

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Transcript

[Chelsea Handler]

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Did you see that our friend Boom Boom Hiller won an Emmy?

I did see that. Boom Boom Hiller won an Emmy. That's very exciting. Yes. I was very happy for him. He gave a great, great speech. I didn't understand what was going on with the Emmys, with the money. What was the money thing? I tuned in, like, halfway through.

I also tuned in, like, halfway through. I think they should just let people who won talk, don't you? I mean, you've hosted these awards shows. Like, what's your opinion on that?

I just feel like that's the moment people get to talk. I mean, obviously, within reason. Don't go crazy. I thought they were deducting people. They were deducting money from a charity for people who were going over their time.

They were taking money back from the charity.

Yeah, that's what they were doing.

[Sponsor Announcer]

I think.

[Chelsea Handler]

I'm pretty sure that they were basically. They had a set number, and anyone who talked over it became an average. Yes. So I was like, that's pretty fucked up. But who knows? I mean, I can't really even track a conversation. So who knows what I was thinking? I was kind of half watching. I had just. I went to New York again this weekend, so I had.

Were you in there?

I was. I had a show, actually. I had a show. Oh, I just announced a new tour, you guys. That's what I want to talk about. I announced the High and Mighty Tour, which I'm going to start next year. I Start in Washington, D.C. next January or February. I don't know. It's called the High and Mighty Tour. Tickets are on sale, and I'm going to lots of different cities, and you can check my website, chelseahandler.com for tickets, or you could Go to the link in my Instagram to buy tickets.

That's great.

So that's what's happening there. And we have a very exciting guest. Okay, so I saw a movie. I actually moderated a conversation for a director named Susannah Fogel, who directed a movie about Reality Winner. This is a girl's real name. This is our guest's real name.

Today, when you first texted me and said, I wanna talk to Reality Winner, I was like, winner of what reality show? Like, I did not get her.

Her name is Reality Winner. And if you don't remember who she is, she was a whistleblower during Trump's first term. She was working at the nsa and she leaked some document. To Intercept. Yeah, to the Intercept. And then the FBI basically arrested her. They came, they interrogated her, they went, showed up at her house on a Saturday afternoon. And anyway, she's a former linguist, she's an intelligence analyst. She was arrested in 2017 for leaking classified documents about the Russian interference in the 2016 election. And there is some backstory that our listeners should know about before we get into this conversation. Reality was in the Air Force. Does a linguist. She translated conversations for government targets. And then when she left, she started a contract with the nsa, and she outlines that there are certain news sources that people who work for the NSA are allowed to read that are not available to the general public, but people with security clearance are not allowed to read mass news the way civilians are.

Right. So she explains in pretty great detail in the book how as a person who has a high security clearance working for the nsa, she had access to a specific news outlet that was only for people with a high security clearance. But there was also sort of this rule that she couldn't go look at New York Times, she couldn't go look at Washington Post, and if they had found something like that, like links to that on her phone, anything like that, then she would have been in trouble. So there is this sort of weird dichotomy that people with high levels of Top Secret clearance do have access to more information, but they also don't necessarily have what all of the rest of us have access to. So the document, and it was just one document that she leaked, was from this news source that she had access to as a person with high security clearance.

So she felt that she needed to release this document about Russian interference in the election so the American people would know it happened. And then the FBI found out, confronted her in her home in a three hour interview during which she was not read her Miranda rights. She Also had a dog and cat at her home that were unpredictable. She describes feeling terrified that they'd hurt her animals or use their behavior as an. An excuse to hurt her. She was taken to jail, where she stayed for about a year before going to prison for four more years. And then her mom lived in her house nearby while she was incarcerated, which she says saved her life. And then once she was out, she had a period of readjustment. She says even the colors outside were overwhelming for her. After five years of staring at gray walls, she briefly got married and then quickly divorced to an old boyfriend who had a child. This was part of her rebellion during her readjustment period. And now she has written a. Her experience has moved on romantically and is in veterinary tech school. So there are a few movies out about her.

There was a Broadway show.

There was a Broadway. Yes, a Broadway show. And now she has a book called I Am not yout Enemy. That's a little background information for you. So please welcome Reality winner. Hi, Reality.

[Sponsor Announcer]

Hey, Chelsea.

[Reality Winner]

Hi.

[Chelsea Handler]

How are you?

[Reality Winner]

I'm good. Thanks for having me. How are you?

[Chelsea Handler]

Oh, I'm great. I always want to say we'll commence, but I feel like Commence says we're starting. Does it commence? Does this mean we're starting something or we're finishing something? I'm getting confused with my Spanish.

Yeah, Commence is starting.

Commencement speech, though, at a graduation is the end.

[Reality Winner]

Yeah.

[Chelsea Handler]

Well, you're commencing into life.

[Sponsor Announcer]

Is that right?

[Chelsea Handler]

Okay. Okay. Okay. We have Reality winner here. Reality. You and I go way back, but you don't know it. I'm sure a lot of people feel that way about you. First of all, I'm just happy to see you out of prison. I actually moderated a conversation between Susanna Fogle. Do you know Susanna?

[Reality Winner]

I love her. Yes.

[Chelsea Handler]

Yes. Okay, great. She directed a movie, one of the movies. So there's three movies out about your story. Reality winner was a whistleblower in the year 2016 with relation to the Russian interference in the 2016 election, and subsequently went to jail and then prison because of that. So there was a documentary about you, which I also watched. And then there was a movie with Sydney Sweeney. I skipped that one. And then the one with Susannah Fogle, who starred, who was the star of that reality?

[Reality Winner]

Emilia Jones.

[Chelsea Handler]

Amelia Jones, who's fucking phenomenal. Did you love that movie?

[Reality Winner]

I don't watch anything about me because I have a very, like, physical trauma response.

[Chelsea Handler]

Okay, I understand that. I understand that. How are you doing today?

[Reality Winner]

I'm doing so good today. My biggest issue Was having to get to the studio. I hate driving on overpasses. They're my nemesis.

[Chelsea Handler]

Really? Why?

[Reality Winner]

They're so high. Why?

[Chelsea Handler]

What about bridges?

[Reality Winner]

No, you won't drive over a bridge. No.

[Chelsea Handler]

Do you know that when I was a little girl, our family used to drive up to Martha's Vineyard every summer? So you drive from New Jersey? We grew up in New Jersey. We drive to Woods Hole, Massachusetts. And you would have to drive over a bridge called the Tappan Zee Bridge. That's outside of New York. And it was. You know how big bridges are. They have all of that iron work over them. Right. But that's not the actual pavement. But my brothers and sisters convinced me that we had to drive up over the ironwork every time. So I would crouch down and cover my head. Cause I was so scared. I'm like, oh, my God. How are we going to stay on? They're like, we might not let cars fall off all the time. And so anytime. So I have bridge trauma, too.

[Reality Winner]

Yeah.

[Chelsea Handler]

I hate them.

But it sounds like you have lower bridge trauma.

[Reality Winner]

Right. There is some bridges out here. Like, the only way to get to the beach is on a bridge. And it's not fun to be in the car with me. I have to drive. I have to be in charge of my own death. But it's horrible.

[Chelsea Handler]

Well, I think after everything you've been through, it's fine for you to want to be in charge of your own death and your own life at this point. Right. How long have you been out of prison?

[Sponsor Announcer]

Officially?

[Reality Winner]

I have been out for four years.

[Chelsea Handler]

Okay, so you wrote this book, obviously, after that. And the book takes us through your journey. The book is called I am not your enemy Reality winner. So let's go through your history because you joined the Air Force and then you decided that you wanted to go work at the nsa.

[Reality Winner]

Correct.

[Chelsea Handler]

And take us through what happened when you started working at the nsa.

[Reality Winner]

So in the transition from the Air Force to the nsa, I already knew it was a temporary position. I had my sights set on getting a position in Afghanistan proper, but that in order to be eligible for those deployments, I would have to keep my security clearance current because that's what the recruiters were looking for. So I was coming up on a very important deadline, and I just took any contract that would have me. So that was the particular position that I was working at in Georgia at the time of my arrest or at the time I committed the felony. There was nothing for me to do. I just sat there and watched YouTube all day. And Planned out my workouts and my yoga classes. They didn't really know I was there. And looking back, being so disconnected from any sort of purpose or mission is definitely one of those things that left me vulnerable to doing something so naive.

[Chelsea Handler]

Or naive is the word that you use a lot. And I also don't really think you're naive. I think that from your books and from what I've learned about you, that you really just had a sense of right and wrong and that you wanted to share. And I think that's very admirable. And I think what you did, yeah, you're young. I think you were young and didn't realize, which you revealed in the documentary, that you didn't realize what the consequences would be. In fact, you didn't even really consider the consequences of sharing the information that you were privy to.

[Reality Winner]

I didn't. I mean, I just really thought that at the end of the day, no damage was done. It was very clear that I did what I did for the greater good and that, you know, I was definitely going to lose my job, but did not imagine the statements that the government would then make about me and my character.

[Chelsea Handler]

Following this and at this time in your life, were you familiar with people like Julian Assange?

[Reality Winner]

So, on the surface, yes, I knew about Edward Snowden and Chelsea Manning. But because of the technicality, they were able to keep us from knowing any of the specifics about these individuals every week or so, especially when the news cycle would be very much focused on one of those individuals that if you read this Washington Post article and it was derived off of classified information and you read it on your personal device, you are then carrying around classified information and you could be charged with the Espionage Act. So it was a way to make sure that we were kept in the dark on what life is like when you're charged with these sort of crimes and that I didn't know anything about Snowden or Chelsea at all. I didn't know what their legal defense was like. I didn't really know what they had gone through. I was just kind of acting in the dark at that point.

[Chelsea Handler]

And the reason that you acted was because you felt what I felt like.

[Reality Winner]

If the American people had the information on that document and they could see it in black and white, that a would answer a question that was. I felt like it was burning a hole in our society in 2017. And I wanted to give the American people a way to decode media bias. If they had the full story, they could see, like, the people I trust on the TV aren't giving me the whole story. Like, I can see everything right here, and they're leaving half of it out.

[Chelsea Handler]

And so can you take us through what happened on that Saturday morning after you had printed the. So you had printed the document. Was it on a Friday, right in your office?

[Reality Winner]

I had actually printed it on, like a Monday or Tuesday, and I think I mailed it out on a Tuesday night. And it wasn't for about two and a half weeks until the FBI came to my house.

[Chelsea Handler]

And I think we should also point out, you know, the Intercept, which is who you sent the document to, kind.

Of was like, outed her.

Yeah, they bungled the situation. They have all these high level people who know how to handle whistleblowers. And your document went to two journalists who did not know how to do that. And instead their mistake wound up eventually in your conviction.

[Reality Winner]

Mistake? It was not a mistake. It was on purpose. It's by design. I was the third. Well, actually, Terry was the third. But there were three of us in a very short succession that were sort of outed by their incompetence, but then championed by them. So they would create victims and martyrs and then try to be the only media outlet fairly reporting on them.

[Chelsea Handler]

So take us through what happened to you on that Saturday when the FBI did show up at your house because you were getting ready to go on a date that night anyway.

[Reality Winner]

Exactly. The ultimate ghosting.

[Chelsea Handler]

Oh, that's funny. Yeah.

[Reality Winner]

Not only did I not show up, but he was probably interrogated as well. Poor guy.

[Chelsea Handler]

Oh, true.

I bet.

[Reality Winner]

So I parked with my groceries, and immediately a black vehicle comes up behind my car and parks me in. And Garrick and Taylor come out. They introduce themselves, they showed the warrant, and I knew what it was about, obviously, because I had done the thing. But they said they were looking for documents, and I was like, whew, I only had one document and I sent it out. Like, that's kind of one of the reasons why I was just so compliant. I was just like, okay, search my house. The only thing that started to get scary was that there were 11 men. I was pretty sure all of them were armed. And the government was very quick to correct me. Of the 11 agents, only nine of them were armed.

[Chelsea Handler]

Only nine?

[Reality Winner]

Only nine. So I was lying again. You know me, I just can't stop telling lies. And they kept leaving my doors open. And I had just sort of had my early twenties awakening of the injustices of this country and understood that when the police or the FBI, when someone from the government Kills you, they have the only control of the narrative. And so I knew that these men were leaving my doors open and interacting with a dog that had previously been extremely aggressive to men, and that if my cat had gotten out and if I had, like, run down the street after her, would they shoot me in the back? If I became emotional about how they were taking care of my animals or if I thought they were gonna shoot my dog, would they shoot me and then, you know, try me, you know, basically posthumously convict me in the news cycle the next day, they had interrogated me. I did confess. I thought that because they looked like the guys that I worked with at nsa, if I just was straight with them, that whatever was coming next in a court or whatever, I could figure out, and it would be a normal legal process. And that was when Garrick told me, we're gonna have to take you in. You're gonna go in this vehicle over here. So, nondescript, unmarked black vehicle. He said it was gonna be okay because my hands would be cuffed in the front and not the back, and that he would be sitting next to me the whole time, and that he wanted to apologize because it would be a bit of a drive. What little I did know about Chelsea Manning was that when they first took her, she was in solitary confinement in Quantico for nine months, and nobody knew where she was. So when he said that reassuring statement, I understood that I was going to Quantico that night and nobody would know where I was. That was not the case. And even if they had intended to drive me to the jail themselves, the last remaining part of the warrant was a search of my person. And obviously, I was kind of in between dates, so I wasn't wearing much. A visual search would have been just fine, but a female, a woman had to do it. So that was when they called a nearby deputy from the Richmond County Sheriff's office. And I don't know what it was, but she came and assessed the situation. And she took me to a private room and patted me down and executed the search warrant on my person. And she came out and had a conversation that I couldn't hear. And shortly after that, another sheriff's department vehicle came up, and another female officer came out, and she said, hey, I'm gonna be the one taking you to jail. So for the first time, women were on the scene, uniforms were on the scene, marked vehicles were on the scene, and the word jail was spoken. And, I mean, honestly, that was the first time I knew that I was gonna survive that night.

[Chelsea Handler]

At Least because. So that's okay. So. Okay.

Cause there's a paper trail and a record.

Okay.

[Reality Winner]

Yes. I knew my parents could find me then.

[Chelsea Handler]

Your poor parents. My God. I mean, honestly, watching your. I mean, I wanna make you feel bad because I'm sure you have enough guilt to deal with about. With regard to your parents, but what your mother and your stepfather. Is it your stepfather?

[Reality Winner]

Yeah, stepfather.

[Chelsea Handler]

Yeah, yeah. Went through is just like, I wouldn't wish that on any mother, you know, and fighting so hard on your behalf and having to hear. And also, you know, coming. Really, there is just nothing better than a good mother. There really is no. Nothing better in life than having a good mother. It's more important than a good father. A good mother is everything. Because she wasn't concerned to let you compromise your values or your goals either. She wasn't going to let you take a deal, which you were given the opportunity to do.

[Reality Winner]

I was initially up front, and then later again, like in November of 2017, offered five years. And we had tried some legal strategies to get that down to four years, and it did not work.

[Chelsea Handler]

And so when you were given that sentence for basically telling the truth, how did you wrap your mind around that psychologically? I know you talk about in the documentary and in the book you did as well about contemplating suicide. And the one thing you didn't want to do was hurt yourself, kill yourself while your mother was alone in your house. Which I thought was just like, oh, my God.

You didn't want your mother to, like, get that.

Get that information while she was.

[Reality Winner]

Yeah, yeah. I think that at that moment in time, the only thing I knew I was going to do it and the only thing I was in control of was the timing where my mother would be when she got the news. We had just gotten word that I would be denied bail again and that I would probably never leave that jail except to go to prison or to trial. And I said, I can't do this anymore. And so I started planning and doing dry runs of my suicide. And the last piece of the puzzle was, hey, I'm not getting out on bail. You need to go back to Texas. You need to go home and get the house in order. And, you know, we'll figure this out later. You know, my attorneys will do some stuff. And she put it off by a week, and then she put it off by another week, and then she put it off by another week, and then she started, like, working at a dog shelter and thinking about adopting a dog in Georgia. And it was like those three Weeks where I was actively trying to get her to start driving and doing that other stuff was going on in those three weeks. And I had kind of hit a rock bottom, which involved me screaming and punching a door after an officer. And I came out and told one of my attorneys, this is what's going on. When you guys call me to the courthouse for this. I can't go outside to yard call. And I know you guys are sick and tired of me saying that I want to go outside. I'm bulimic. I can't do this anymore. I'm bulimic. I'm not functioning. I'm not surviving. And, you know, luckily, people on my legal team were very close to that particular illness. And, you know, you think about, like, you know, men don't take eating disorders seriously. They had very intimate knowledge of how deadly bulimia is. And they said, this is not okay. Like, you are very sick and this has to be taken care of. And when they started initiating that type of care and that type of consideration, I can't say things got better. But I feel like the moment I came out, it felt like all the drive in me to kill myself had just kind of gone away.

[Chelsea Handler]

And then how did that impact your eating disorder when you were in jail or prison at this point? Once you told everybody, then what happened with your eating disorder?

[Reality Winner]

You know, it's so difficult. Like, even in normal daily life, like, you come out about something like that, like, obviously you can't just, like, not eat. You know what I mean? It's not like. It's not like being like, oh, I'm addicted to meth. You know what I mean? People are gonna watch you to see if you're doing meth. If you're like, oh, I have bulimia. People wanna see if you're eating right. It's never really like a relief. It just cuts some tension. And I was medicated, and my legal team altered their interactions with me in a way that would not disrupt the daily schedule of the prison. Then they understood that when they came to have legal meetings with me or when they were calling me to the courthouse and I would miss yard call or being able to go outside, they stopped doing that. They said, we are going to meet her on her own terms and we're only going to try to meet with her after she's gone outside to go run or exercise and just things like that. It made enough of a difference to get me through the winter of 2017.

[Chelsea Handler]

And you talk a lot about the exercise and that kind of Replacing your addiction in a sense. I mean, were you able to actually stop throwing up at that point or did you continue on for a while?

[Reality Winner]

I was able to not throw up and to continue to exercise at an intensity that allowed me to eat. And that was another pressing issue of with my disordered eating, having very severe OCD as to what I would even put into my body. Yeah, I don't even think clinically I could get my hands on enough food that I was willing to eat to do a proper binge. So it was pretty much just trying not to throw up the one meal I would eat that day.

[Chelsea Handler]

Right, Right.

Cause you talk about how it was difficult to get not only like kosher meals, but like meals that didn't have meat or didn't that had things that you could eat that you were okay eating.

[Reality Winner]

I mean, it's crazy, but as a federal inmate, that county jail was required to give me a substitute protein and not just more rice or more corn. When I got to federal prison where it is regulated, there's fried chicken or there's baked beans. Right. They have to have that on the line. It didn't make it easier because you would be discriminated against if you dared hold up the line to ask for the alternative because they're just throwing chicken on trays and trying to push everybody through. You just gotta have a thick skin. And there were several really tense standoffs with officers because, like I said, I dared to ask for the beans.

[Chelsea Handler]

This week we're looking for questions from writers. Whether you're an up and coming writer or you do it for a living, please write in to dearchelseapodcastmail.com Dear Chelsea is sponsored by the RealReal, the best place to shop authenticated luxury bags, clothing, watches, and so much more. I love designer duds like Loewe sunglasses, Kurt Geiger rainbow purses and Miu Miu accessories. But my bank account, as with most of us, has its limits. So I love scouring the RealReal for new pieces. P.S. there are 10,000 new items added every day and they do their daily drops at 10am and 7pm Eastern. I shop and sell on the RealReal, which is great because I can use my earnings for something special and new to me. Unlike other resale sites, everything the RealReal sells is authenticated in person by luxury and fashion experts. The RealReal is great for the planet and your wardrobe. The RealReal has found new homes for over 37 million authenticated luxury items so they know firsthand and the impact resale has on the planet. Rather than producing more stuff, the RealReal is making what already exists new. They're your go to place for your next special piece. Need a dress for that black tie wedding? The perfect vacation sandals? Ready to invest in a new bag to add to your collection? Find exactly what you're looking for that no one else has at the RealReal. The RealReal is the world's largest and most trusted resource for authenticated luxury resale. With thousands of new arrivals daily. No one does resale like the RealReal. And now get 25 doll off your first purchase when you go to therealreal.com Chelsea that's therealreal.com Chelsea to get your $25 off, start shopping now at therealreal.com.

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[Chelsea Handler]

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[Chelsea Handler]

Literally.

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[Chelsea Handler]

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[Chelsea Handler]

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[Chelsea Handler]

Did you make any friends in prison?

[Reality Winner]

Lots. Yeah?

[Chelsea Handler]

People you still keep in touch with?

[Reality Winner]

Absolutely. I went and ran a half marathon with one of my friends, Stephanie, and my family got to meet her and they added her on Facebook. She's great. She's doing so well.

[Chelsea Handler]

I'm so proud of her oh, wow. Yeah. So talk to us about what it was like to come out of prison after spending that much time there. When you did come out four years ago, talk to us a little bit about leading up to that moment. And then the actuality. I know you have ideas. People talk about these kinds of huge changes that you have ideas of what it's going to be like, and then the reality of what it is like can be kind of counterintuitive to a degree.

[Reality Winner]

Absolutely. I mean, when you're inside those four walls of the prison, it's like, give me an ankle monitor. I don't care. I would do anything just to be home. And in the year leading up to my release, the COVID pandemic had happened. We had had several unwarranted lockdowns and being put in county jail type conditions all over again. And I had just become so disruptive and violent and using drugs, getting girlfriends, getting into fights, that by the time that version of me walked out of that prison, I was almost unrecognizable to my family. Even mild disagreements would get loud with me. I didn't know how to relate because the things that I thought were funny were like, you know what I mean? They were so inappropriate all the time, which was fine. But I don't think anybody gave me or my family the vocabulary to sort of talk through the process of decompressing a huge trauma. Right. Leading up to my release is that I spent 23 days in a single hospital room as part of a Covid quarantine procedure. It was just so de. Socializing to a certain extent. And I feel like. Not ashamed, but just like, God, the person I had to become to get through that with any type of stability. Or, you know, we were. We were literally like, okay, you're going to put us in a room like mental patients. We're going to act like mental patients. I mean, we did. And then to come out, the pressure was, if your parents do anything public, if they announce that you're home, we might not be able to keep you at home. At every step of the way, that halfway house threatened my ability to be on home confinement. I did two drug tests a week. I was not ever authorized to drive myself, so my parents had to take off work to drive an hour and an hour back. Just constant drug testing when I didn't even have a drug charge. Like, yes, I know I did drugs, right? Like, we can all say, like, oh, she did drugs while she was in. It's in the memoir at that point in time, like, the federal government had zero documentation of substances being in my body, but I'm being tested constantly. If the ankle monitor would buzz, if it would be on low battery. One time I missed a phone call because I was on the phone with my boss, and I called the guy back and he was like, oh, okay. Well, I had already documented as having escaped. I was constantly under so much pressure from the top down, from the government down, that the only way that pressure could come out was sideways. And so my family were. They were the sideways. They were in my line of fire since I couldn't do anything to ease the government pressure off of me. So things were really toxic those first six months.

[Chelsea Handler]

Wow. How about your sister?

[Reality Winner]

Luckily, she was protected out of the picture. She was in North Carolina. She did bring her. Her niece. My niece down. Her daughter. She brought her down to visit. I got to meet my niece for the first time or second time because they surprised me getting out of prison. She and baby were there waiting outside the prison for me. I know for her it was hard, but she also had a one year old daughter, so that probably gave her a really nice little buffer zone between the absolute dumpster fire that I was.

[Chelsea Handler]

And what do you think? What was the shift that happened after about six months? Just did. Did. Did it start to depressurize, like, everything surrounding your case and your kind of like their oversight of you?

[Reality Winner]

I think a really big part of it was, yes. I secretly married Carlos in my backyard, and then 67 days later, that relationship fell apart. And, you know, my parents didn't talk about it, but I think that once it had completely fallen apart, you know, day 67, I said, okay, like, his shit is out of this house. Like, I made him come get it. And, you know, was like, I'm gonna start figuring out how to secretly get divorced from my living room. Right. It felt like one of the biggest barriers between me and my parents was lifted. And honestly, like, it's really ugly to say this, but a big part of it was the fact that he had a daughter who was. She was four at the time, and he would bring her over. And, you know, my mother felt like I wasn't supposed to bond to this child while my sister and her baby existed. Like, oh, you got out of prison, you got to meet your baby niece. Oh, but now you're playing stepmom to a four year old. Like, I thought you wanted to be an aunt for your sister's baby, or.

[Chelsea Handler]

Were you in any condition to be in that role in the first place?

[Reality Winner]

Well, I was Fucking better than he was at it, that's for fucking sure. But when I found out he was getting high again and stuff like that, I mean, you know, it and part of getting married, I knew he was terrible, but I thought, again, like, this girl was brilliant. Four years old, taught herself how to read. Her mom really didn't want to be a mom, which is why she was. She spent 90% of her time with her alcoholic, high, you know, piece of shit father. And I just thought, well, God damn, like, even with this ankle monitor, I'm better than both of them combined.

[Chelsea Handler]

And isn't it amazing, though, when you think back and look at that kind of decision making, like marrying Carlos in the first place. Like, when you look at your. The state that you were in, how newly out of prison you were, what your parents must have thought about that. I mean, you know, you discussed that too, and it's obvious. But when you look back at that decision making, don't you just know that you were in no position to make any of those decisions? Like you were dealing with so much trauma that you hadn't even begun to unearth?

[Reality Winner]

Yeah. And I think that when someone's drowning in trauma, the worst thing you can do is point out that they're traumatized.

[Chelsea Handler]

Right.

[Reality Winner]

And that I was. I hate it when people say this, but they're. They. They do say it. Inmate thinking patterns. The way you think and operate as an inmate is you find what you want and you find a way to secure it in a way that an officer or a position of authority cannot take it away from you. So I knew that I wanted to be with Carlos and I wanted to be a family to that little girl. And I was just thinking, like, a, my parents can't say anything if we're married, but B, if I do wind up back in custody, the government can never deny me access to the two of them if we're legally married.

[Chelsea Handler]

Okay?

[Reality Winner]

So it was the absolute. Like, you just grab something and you're just like, no, you can't take this away from me because I have this legal document and you're constantly trying to be two steps ahead of the police. And that's where that decision making was from. And again, as a family unit, nobody had that sort of. Nobody had the vocabulary to sit me down and say, nobody's going to take him away from you. We don't like him. We don't agree with him. We're not going to let you go back into custody, but nobody's going to make it illegal for you guys to Interact. And because I didn't get that assurance, I married him secretly. And once that disintegrated, I felt like everything got better. With my parents, obviously, like, the way relationships go. We did see each other one more time. And that was when I saw firsthand the way he was gonna use access to his daughter to get behavior that he wanted from me.

[Chelsea Handler]

Yeah.

[Reality Winner]

And that was when I walked away permanently. And I never saw either of them again. Wow.

[Chelsea Handler]

It's like trauma on top of trauma on top of trauma.

[Reality Winner]

I just keep asking for it. I make shit decisions.

[Chelsea Handler]

No, no, no, no. You're gonna get better at making life decisions. You already have. You're gonna get better. That's just a period in time that's not permanent. Nothing's permanent. You know, look, you're out. This is different. I mean, I have a lot of faith in your future. Do you?

[Reality Winner]

I mean, I guess I think you just lead.

[Chelsea Handler]

You're just such a heart leader. You know, you lead with your heart so much that. That's been your issue, I think, you know, with. When you say you're terrible at making decisions, you're le. You're making decisions with your heart rather than using your head. But with all of this experience that you now have, you're going to make better decisions. It's like a math equation. You're smart. You're too smart to keep repeating those decisions. And I don't think the first decision was necessarily framed as a bad decision. It was like, it's based on the.

Courage of your convictions, that it was what you believed in.

I wouldn't frame that as bad. You just didn't realize the consequences. So it was naive, as you say. It was young, but it wasn't like you did something wrong. You didn't do something wrong. You know, I would like to think that I would have those same convictions in your situation. So now where are you? Where are you with all of your trauma? How do you feel about everything? And how do you feel about your life moving forward? And how do you frame the past?

[Reality Winner]

So one of the best parts about being back in my hometown is I get to be anonymous people when they realize that I'm reality winner. It's usually like, oh, you're Billi's daughter. And so everybody wants to know how my mom and my sister are doing. People don't really make the connection to what I did. The people down here are very conservative, but they also don't follow national news there, which has kind of been my hiding place. I'm just Coach Re And I've been coaching CrossFit now for four years. It's a cult. But it's also what keeps me from being bulimic. It's like the only cure that I've ever found so far. And, you know, I rescue dogs. And I recently started a veterinary technology program at the local university, which is the hardest thing I've ever done. And the travel restrictions are even more like, I'm not traveling, I'm not going anywhere. Like, I basically signed up for three more years of federal probation.

[Chelsea Handler]

What do you mean basically signed up?

[Reality Winner]

Literally, if you miss more than two days, you're out of the program.

[Chelsea Handler]

The vet tech program?

[Reality Winner]

Yes. I felt more nervous asking for one day of missed class to go on book tour the week of publication than I ever did asking my probation officer to travel.

[Chelsea Handler]

You said you were surprised that they used the dog in the movie. That they had the dog in the movie. Why did that surprise you that they.

Had you stealing a dog in the movie?

Yes.

Which you had never done at that time.

Oh, yeah.

[Reality Winner]

I had actually never stolen a dog. My friends stole a dog for me back in May and I just thought that was like a funny continuation of like how that movie played out. That was the only scene I've ever seen from that movie. I just thought it was so delightful and.

[Chelsea Handler]

It is delightful.

[Reality Winner]

It is, it's so funny. I wasn't even really into animal rescue at the time of my arrest. You know, it's just kind of been a self fulfilling prophecy. Like, the more people talk about it, the more I started doing it in my own life.

[Chelsea Handler]

And what do you think are, like, some of, like, what do you think is your biggest takeaway from spending all that time locked up and being treated as a criminal? Like, what do you think that did to your spirit? Like, do you feel stronger now?

[Reality Winner]

I don't necessarily feel stronger. I do feel a little bit more brittle. Kind of like, I know if you hit this glass against a table the right way, it's gonna shatter. You know, I know what can take me down really quickly. You know, I've often said, like, what doesn't kill you just doesn't kill you. But I do think that getting to interact with people from a background that I never would have before and sort of breaking down, like, I mean, when I was growing up, I was constantly just around other brilliant children, even in high school. You know, all my friends right now are like, they're all doctors. They're just insanely successful people. And even in the military, being around other people like Me that could learn languages. I've never been around normal people until I was in that county jail. And that's kind of what burst my bubble and helped me understand my own country. I thought I was interested in social justice in the United States, and then I got locked up and I got really interested in it very fast. Because you do realize that what is happening to millions of other Americans can happen to you at any time. And that all of us are one interaction with law enforcement away from being in solitary confinement without legal justification. And what we're seeing now with, you know, these ICE raids going on and, you know, citizens getting detained under immigration law, which is ridiculous. Like, it's so scary right now to the point to where I never thought that this is where we were going as a country. My basic understanding was, yeah, if they charge you with a crime, they can do anything to you after that. And now they don't even have to charge you.

[Chelsea Handler]

Ugh. It is. Yeah. That's very scary to think about, especially when you put it like that. What do you want out of life now that you have one?

[Reality Winner]

Honestly, I just want to know that my community is a better place because I'm in it. And like most people, I want to be comfortable in my life. I want enough to get by. I want to fence in my 10 acres and open a dog sanctuary. You know, I mean, my view of the world has gotten a lot smaller with this criminal conviction. Not being able to have the high positions that I wanted to do. I. I can't even coach troubled kids. You know, I can't be a mentor yet. You have to have 10 years clearance from your last day of your sentence. My sentence didn't end until last November, so in 2034, I might be eligible to be a mentor for children caught up in the criminal justice system.

[Chelsea Handler]

I'm surprised they allowed you to write a book.

[Reality Winner]

I am allowed. I can't make any money from it. And the NSA took two years to clear that manuscript.

[Chelsea Handler]

Really? You could even make. So where does the money go?

[Reality Winner]

So I gave everything to my agent because I love him. Not in a weird, like, creepy way, but he. He found me and he didn't even know I couldn't make money from it. This was all conversations we had later on once we found a publisher. As of right now, I don't have any documentation to say otherwise, but proceeds from this book will go to charity. We just. We waited two years for the NSA to clear the manuscript. When the time comes, we will make a statement on which charities are and you know, what percent of proceeds and how that works out legally. But I do plan on being as transparent as possible.

[Chelsea Handler]

And do you want to have a family?

[Reality Winner]

I have eight dogs, three cats, and somebody named Eddie.

[Chelsea Handler]

So is that a man in your life or is that another animal?

[Reality Winner]

He's a man, unfortunately.

[Chelsea Handler]

No. No, no, no. That's not unfortunate. I'm glad that you have someone that you care about. I want that for you. And I also just want you to like, you're an inspiration, you know, I hope you do. You feel that way.

[Reality Winner]

I don't. I just, I'm like, looking back, like, I could have done things so much better and I could have been somebody that the government couldn't say these terrible things about, even though 99% of them weren't true. You know, it's really hard to continually absorb the things that were said about you in the courtroom that are like, there's just enough truth in that statement, like, to where you actually just believe everything they said about you. And I'm still reckoning with that today. Like I said, I don't use my name in a lot of social situations. And just admitting that I went to prison, you know, the biggest compliment that I get is if I bring it up, people just think I went for, like, method. And I'm like, I'm willing to go along with that. Like, yeah, sure.

[Chelsea Handler]

No, no, it's so much more than that because, I mean, I don't think you're taking into account that you survived all of this. You know, of course it's not ideal. Of course you don't want anyone to be saying, you know, to be propagating lies or perpetuating lies about you. No, but you survived all of this. You have a job and you care about your, like, place in the community. Look at all these animals that you're helping, like your parent, you're with your fam, you know, like, there's so many good. Even though this is not an ideal situation and you would, if you had to repeat it, you would not have repeated it. You are here with us today and there are lessons for you to still continue to learn. And, and, and your story, like, sharing this book with the world, is going to be tremendously helpful, I think, and cathartic for your healing process. I mean, I'm assuming you're already in therapy. I mean, you'd have to be, right? You have been in therapy for a while. Yeah.

[Reality Winner]

Therapy and me don't get along well because for three years of probation I was court ordered to do it. I had to be in a program without being provided the healthcare for it, so I was like a lot of paying out of pocket. So like for me, it just led such a bad taste in my mouth. But I have been able to kind of get my veterans benefits back up and running.

[Chelsea Handler]

Oh, that's great.

[Reality Winner]

Yeah, so I was properly diagnosed last fall and have been doing a lot better with my mental health and a sort of regimen for that.

[Chelsea Handler]

And you need to reclaim that too. You know, you need to reclaim therapy because that's yours for the taking, not theirs to leave a bad taste in your mouth.

[Reality Winner]

Yeah, I mean, I'll just do a bunch of podcasts till I feel better about myself.

[Chelsea Handler]

Absolutely. Just keep talking and talking and spreading the good word.

Well, and Chelsea, I think you're so right. Like this book, I feel like is such a turning point where 10, 20 years down the road you may have a better understanding of why you went through what you went through. But this is just the beginning of that. Like, this feels like a starting point, a commencement. Like we talked about earlier.

We have to figure out what commencement means because I'm still, I keep looking up that word. I'm like, is it a beginning or an end?

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[Chelsea Handler]

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[Chelsea Handler]

My feet. Are you excited yet? I've been wearing ultra running shoes lately and honestly, life changing. They're now my go to for everything from runs to hikes to dog walks, to airport sprints, you name it. They've got extra room up front so your toes can actually spread out and move the way that they're supposed to, which is way better than most running shoes that cram my toes together. Plus the lower heel drop means your stride feels more natural. It's like my body finally went, oh, this is how we're supposed to move. They are crazy comfortable. And yes, they help me chase that runner's high. You know Mama loves her dopamine and feeling strong and actually wanting to work out. So if you're getting into running, getting back into it, or just want healthier feet so you can get on a feed finder. Altra is where it's at. Find them at altarrunning.com and use code Chelsea for 10% off your order. That's a L T R-A running dot com. Stay out there.

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[Chelsea Handler]

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[Chelsea Handler]

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[Chelsea Handler]

Okay, let's have a real talk. Menopause is a whole thing in case you hadn't heard about it, your body's changing, your hormones are on a wild ride, and suddenly your libido takes a sabbatical. Love that for us. But here is the good news. You are not alone, and you're definitely not out of options. Let's take it from the experts at Vagisil. You know them, you love them, and let's help launch their new menopause support line. It's made with advanced probiotic technology and formulated specifically for the mature microbiome. Because at our age, our intimate health deserves VIP treatment. We've earned it. There's a whole line of care products for you to try. A foam wash balanced at the right PH for a more mature microbiome, an intimate gel that actually makes things feel good again, and a daily supplement that supports urinary health. Because the last thing you need when you're going through menopause is a surprise down below. So when menopause feels like it's changing everything, try Vagisil Menopause Support. The right kind of care can change the way your menopause feels. New menopause support by Vagisil, but no reality. I think that it's so funny that your name is Reality Winner. I mean, honestly, try to be anonymous with a name like Reality Winner. Right. But I really do think, like, you haven't seen. I know you've been out for four years, but you haven't seen the lessons that are going to come from this just yet. And to be open to whatever comes your way and the fact that you're so open and so willing to share your story and that you don't have. Yes, of course there's bitterness, but you don't come across as someone who is bitter and enveloped in your bitterness. Do you know what I mean? You're loving and you're sweet and like. And to remain, to have those things remaining within you is quite a feat. And it speaks volumes about your true character and who you really are, as opposed to all of the things that have been said about you that are not true.

[Reality Winner]

Yeah, I think 2025 for me has been difficult because we're right back in the same position we were in 2017. Yeah, of course.

[Chelsea Handler]

It's very triggering for you.

[Reality Winner]

So triggering. I mean, one of the jokes we have is like, you know, the last time around, I only made it four months before I broke the law. And I think right now you've already doubled your time.

[Chelsea Handler]

You've already doubled. It's eight months.

[Reality Winner]

I know. I have little tick marks you know what I mean? But it's like the guilt of that then was like last time I was willing to act. And now, like so many millions of Americans, I don't want to lose everything all over again. I don't.

[Chelsea Handler]

Right.

[Reality Winner]

You know, am I supposed to be out there? I mean, and of course, where I live, in the middle of nowhere. You know, we're not in a big city, we're not in la, we're not Chicago right now. What am I supposed to do? Am I supposed to drive to Chicago and put my body between victims and masked agents, masked kidnappers? You know, what am I supposed to do?

[Chelsea Handler]

You've done what you're supposed to do. You're not supposed to be involved in anything else. You need to keep yourself safe and sane. That's your main objective. And take care of all of your animals and have a good time with your boyfriend. That's what I want you to do. Those are doctor's orders. I'm a medical professional. I'm actually not, so I can't say that, but I think I am. So. But that's. You've done your. You've done your time, literally, and you've. Your contribution to society. Leave that up to everybody else and just focus on getting yourself healthy and as happy as possible. Cause I want you to have a really full life. And you know, you're still young, you have a whole life ahead of you and this guy's not gonna be president for the rest of our lives. This is only a four year stint. Even though, you know, other things have. So just don't even, you know, that's not your problem anymore. But I do wanna thank you. I want all of our listeners to pick up a copy of I Am not yout Enemy by Reality winner. This book is really important and it's important to just. If you care about your country, it's important to read. And if you care about being a strong woman who has, stands up for something and has convictions, it's important for you to read. And it's a story about surviving. It really is. You're a survivor and you went through. You went through hell and you're still here to talk about it. And that in and of itself just shows that you have a purpose. And so thank you for coming on the podcast and I really wish you all the best.

[Reality Winner]

Thank you so much for having me. I mean, like, I'm such a huge fan and I just really appreciate you taking the time.

[Chelsea Handler]

Absolutely. It was my pleasure. And I was just. When I met Susannah and She's like, oh, will you moderate this film? I just. I was like, oh, my God, yes, I know that story. So I was just, yeah, thrilled to be a part of that as well. And I'm gonna text her right now as soon as we get off and let her know that I got to meet you.

[Reality Winner]

I can't wait to see her next week.

[Chelsea Handler]

Oh, good. You're gonna see her. Okay. Tell her I say hi, will you?

[Reality Winner]

I will.

[Chelsea Handler]

Okay. Okay. Bye. Reality. Thank you so much. Sending you huge love.

[Reality Winner]

Bye. Thank you.

[Chelsea Handler]

Bye. I put up new Vegas dates, by the way, for next year. This year I will be there November 1st and November 29th. Those are my last two dates this year. Then I start up again January 31, March 7, April 18, and May 30. And tickets are now on sale for all of those dates.

Do you want advice from Chelsea? Write in to dearchelsea podcastmail.com Find full video episodes of Dear Chelsea on YouTube by searching ear. Chelsea Pod Dear Chelsea is edited and engineered by Brad Dickert executive producer Kathryn Law. And be sure to check out our.

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[Chelsea Handler]

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[Chelsea Handler]

You begged. They listened. After years of customers asking for it, Barkbox finally put together a collection of their most questionable toys. The Bark After Dark collection is for all the booty sniffers, tail chasers and leg humpers. Very spicy, deeply suspect, and one that you definitely can't open at work. So however your dog likes to play, there's no judgment here. Join Barkbox now to get the Bark After Dark collection delivered discreetly to your door. And let the panting begin. Subscribe today at Bark Co and get double the Bark After Dark goodies in your first box. You know that feeling when you come home late from work and those puppy dog eyes just pierce right through your soul? Yep, we've all been there. Pet parent guilt is real and completely normal. That's exactly why Hill's Pet Nutrition exists. They understand that being a pet parent means being human. Hill's Science led nutrition helps you give more love than humanly possible. Whether it's those long work days or trying to balance the tension between multiple pets. Hills Pet nutrition gets it because you're only human. There's Hills. Science does more. Ready to let go of the guilt? Find the right [e-mail] iheartra that's hillspet.com.

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[Chelsea Handler]

This is an iHeart podcast.