You're Wrong About

Quarantine Deep Dive: Jessica Simpson’s “Open Book” (The Conclusion!)

June 08, 2020 You're Wrong About
You're Wrong About
Quarantine Deep Dive: Jessica Simpson’s “Open Book” (The Conclusion!)
Show Notes Transcript

“You really shouldn’t date people who go in thinking, ’This person has good bones but they’re a fixer-upper.’”

This week, we complete our Jessica Simpson book club with the appearance of a new man who triggers some old anxieties. Digressions include Dolly Parton, mom jeans and a forgotten Hollywood power couple. We talk about “Garden State” longer than we intended. Mike finally gets to tell the octopus story, which he thinks about all the time.

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Sarah's other show, Why Are Dads
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Sarah: I feel like you find your calling authentically when you realize it doesn't fit the grand heroic dreams you have for yourself. And I'm pretty sure that my calling is to be a clown.

Mike: Sarah’s turn to do a tag line.

Sarah: Okay. Welcome to You're Wrong About, where sometimes one woman gets out of the basement.

Mike: Oooh, that's good. 

Sarah: Is that too depressing? 

Mike: That's good. 

Sarah: Cause I'm thinking of Michelle Remembers and how like our last deep dive was this long book about this woman who, in my opinion, kind of didn't get out of the basement. And my hope is that Jessica is going to get out of the basement. And I'm very excited for that.

Mike:  I'm Michael Hobbes. I'm a reporter for the Huffington Post.

Sarah:  I am Sarah Marshall. I'm working on a book about the Satanic Panic.

Mike: And  we're on Patreon, and PayPal, and lots of other ways for you to support us if you look in the description. And things are even weirder now than they have been in quarantine, and so as always, don't feel obligated. And if you want to not support us and support something else, we get it. 

Sarah: Like maybe they are causes that seem more worthy than like two white people sitting in a closet talking about pop stars.

Mike: It's possible. And today, yes, we are talking about the denouement, which I'm pronouncing perfectly, of the Jessica Simpson story. Because times are so weird, I'm like an emotional powder keg right now. It's very comforting to be recording a podcast with you where we just talk about trash men for like three hours. This is our happy place. And it makes me feel really good to be spending a Sunday morning doing this with you.

Sarah: Me, too. And listeners, maybe this is also your comfort zone. And if it is, then welcome. And the closet I am sitting in is very small, but in a more emotional realm, you are all here with me and you all have large stuffed trout to be hugging, as I am doing right now.

Mike: So Sarah, do you want to catch us up? Where did we leave Jessica? Where was Jessica last time we left her?

Sarah:  I feel like we left her in Walmart and you're like, who had Jessica last? The last time we saw Jessica, she had ended her marriage with Nick, she's independent for the first time in her life, she got a place to live. She's moved out of the gigantic Newlyweds house. And we've heard that she's dating a lot because she's never been single before. And that's my image of where we have left her.

Mike: Yes. And because we are going to spend a lot of this episode talking about him, I thought we would start off with John Mayer. Are you aware of this person? 

Sarah: Oh my God. Okay. So let me tell you about John Mayer. 

Mike: What's your relationship with Mr. Mayer? 

Sarah: My relationship with John Mayer is confined to the moment in 2001 when Your Body is a Wonderland was on the radio every five minutes. And I will say, with a feeling of regret and acceptance of my 13 year old self, that I really liked that song. I thought it was pretty good. I thought it was cool. I wanted someone to say positive things about my body. And I feel like this actually is getting us back to what John Mayer was in 2001. Cause I feel like he was like a sensitive boy. He was like playing an acoustic guitar in a way that wasn't synonymous with douchiness, maybe yet to the degree that it would become because of him.

Mike: It was a more innocent time. We were like men with guitars are our friends in all, in all circumstances. 

Sarah: Anyway. Yeah. I had a very positive response to him, and so did America and I think he was also kind of crush-worthy for middle school girls because he had, I mean, he was very, he had like a smooth face, you know, he just looked, it was hard to tell what he was, but he didn’t seem very old. He seemed like a grownup. 

Mike: He did  look like a kid from like a baby food commercial. But also, what was also interesting about him was that he did have this kind of music you hear at Starbucks quality, but he also did it with this kind of indie street cred. He managed to maintain that idea of like, I'm an authentic indie dude, even while selling like millions of records.

Sarah: The early 2000s, where like a time when like, it just, it's impossible to overstate how big of a deal Garden State was like that they took over my sophomore year of high school. That was new. You know, the idea that men could express emotions at all, I think was very exciting. And then, you know, we realized maybe that we had hoisted up as Sterling examples of the kind of masculinity we wanted, guys who like maybe had only figured out a couple of things.

Mike:  I mean, I said many dumb things in the early 2000s, but I still distinctly remember referring to Garden State as generation defining. It’s by far the dumbest thing I've ever said.

Sarah: Which it was! Like you weren't wrong. It's just that our generation had so little good stuff to define it. What did we have? We had Gardens State and the Iraq war. I think we could all watch Garden State, especially if we used to love it and be deeply moved by it and just offer love to the part of ourselves that we could not imagine a deeper film. 

Mike: But I mean, I think this is a good transition into what we're going to talk about because we're going to first meet John Mayer in 2010. And this is really the beginning of the end of like the indie boy, darling, I think. So what happens in 2010 is John Mayer gives two interviews back to back, one to Rolling Stone and one to Playboy where he, I mean, there had been rumors that he was kind of a dickhead for a long time, like paparazzi tabloid type rumors, but they hadn't really gone mainstream. And then this is a long quote, but I'm going to read you the whole thing. This is from the Rolling Stone interview where they're asking him about sort of what it's like being famous and what it's like dating as a famous person, because he's ended up in the tabloids quite a bit because he had been dating Jennifer Anniston.

Sarah: Oh wow.

Mike:  And he says, “All I want to do now is fuck the girls I've already fucked because I can't fathom explaining myself to somebody who can't believe I'd be interested in them. And they're going, ‘But you're John Mayer’, so I'm going backwards to move forwards. I'm too freaked out to meet anybody else. ‘What do you think’, he says, ‘Do you think it's going to take meeting somebody who I admire more than I admire myself, but isn't it also about a beautiful vagina? Aren't we talking about a matrix of a couple of different things here? You need to have them be able to go toe to toe with you intellectually, but don't they also have to have a vagina that you could pitch a tent on and just camp out for like a weekend? Doesn't that have to be there too, the Joshua tree of vaginas?’”

Sarah: That's weird, I mean, I appreciate his desire to apparently be shrunken down and tiny and like living on someone's bikini area, but. 

So okay, my main takeaway from this is that he's doing the thing that it is always like fascinating when celebrities do, where he is treating an interview like a free association therapy session.

Mike: This is where it gets so much worse. Just wait. This is from the Playboy interview where he uses the N word. So one of the things they ask him about like, sort of there's these rumors that you're kind of a douchebag, like, would you consider yourself a douchebag? And so he says, “I come on very strong. I'm very, I'm just very, V E R Y. And if you can't handle very, then I'm a douchebag, but I think the world needs a little very, that's why black people love me. The interviewer goes because you're very? And John Mayer says, someone asked me the other day, what does it feel like now to have a hood pass? And by the way, it's sort of a contradiction in terms, because if you really had a hood pass, you could call it a N-word pass. Why are you pulling a punch and calling it a hood pass, if you really have a hood pass?” So it's like, he's using the N word in a sentence about how he can't use the N word. It's like, because if black people really like me, I could say it. 

Sarah: I am fascinated by also the fact that like white people are obsessed with finding loopholes that let them use the N word. Like, I am actually convinced that this explains the bulk of Quentin Tarantino's career. You’re like, no, but I'm, I have to be special in some way though. Right? Like I can find a way.

Mike:  I also think this is the apogee of late 2000s edgy humor. Remember when it was like, I'm different and I’ll sort of say racist stuff, but like I'm satirizing racism.

Sarah: I mean, this is when South Park was considered like the peak of social commentary, you know, it was a different time. 

Mike: I've been an interviewer interviewing someone who's like pretty prominent, and they say something outrageous. And like the two things as a journalist that you want to do in that situation is, first of all, don't let them know how bananas the thing they just said was, because then they’ll stop, And secondly, get themselves to dig deeper. So the interviewer immediately, I guess because it's Playboy, immediately switches and says, “Do black women throw themselves at you?” So like, don't just get him to talk about black people, get him to talk about black women specifically.

Sarah:  If I were the interviewer I would say, hmmm, go on.

Mike: But then this is really bad. So here's the quote, “I don't think I open myself to it. My dick is sort of like a white supremacist. I've got a Benetton heart and a fucking David Duke cock.”

Sarah:  Oh my God, John! Okay. And also like for people who don't know, and I might not actually be 100% sure, but David Duke is like the leader of the Klu Klux Klan or something like that. Why would you ruin your penis forever for everyone? I mean, it just doesn't seem like he's imagining repercussions for any of this. And I don't know how he got that idea, but then again, like it's not like this tanked his career or anyone really remembers it that well, so maybe there weren't any.

Mike: I mean what’s interesting is I think the discourse around all of the things that he's talking about have changed so much since then. Like even in 10 years, there's been a huge social change in the way that we talk about race publicly. And so you could say like, wow, things were so different. Like back in 2010, people could just like, say the N-word and it wasn't that big of a deal, but it was actually a big deal. Like he disappeared from the face of the planet for like two years.

Sarah: Yeah. What happened? Like how did people, like, what are the reactions to this? 

Mike: The reactions were really negative. Like, this was a huge news story. Like it got written up in the New York Times. It got written up everywhere. Like he apologized, he apologized on stage. He apologized in the press and then he basically just like disappeared. He put out two albums in the following two years, but he did no press for them. He's just like, here’s an album. 

Sarah: But it did tank him actually, apparently. Okay.

Mike:  So we are now going to rewind to where he becomes a fixture in Jessica's life. So as you mentioned, Jessica is newly single, she has a new house. Her career is actually going really well now that she got really good sales of her last album. As a result of her being so famous from doing Newlyweds, she's gotten more power at the record company and she started writing her own songs. She eventually puts out an album where she writes 11 of the 13 songs. She's also started her clothing line, which I feel like with celebrities you think like whatever, she licensed her name to like some sweatshirts, like not a big deal. But she's like running the company and she's day-to-day extremely involved. So as she mentioned, the first chapter, this eventually becomes a billion dollar clothing company.

Sarah: I feel like having heard what she's gone through so far, I'm like, yeah, like Jessica Simpson having control of clothes seems like a very meaningful thing. The clothes used to be in charge of her and now the tables have turned.

Mike:  Oh, that's such a nice way to put it. 

Sarah: Thank you. 

Mike: And so this is when she meets John Mayer, in 2006. She had actually met him at various party LA things, but she was still married to Nick. And I guess Nick just like clocked John Mayer immediately and was like, fuck that dude, like with no information.

Sarah: Game recognizes game. 

Mike: He's like one of those people that like dogs bark at for no reason. But then once Nick is out of the picture, John apparently starts emailing her and then they get into this longer and more intense correspondence. And apparently it gets quite intimate, quite fast. She says, “He asked why I would want to be famous as a wife. He said I was so much more than what the world perceived me to be.” So he’s sort of lifting her up and like, you're seen as a simplistic person, but I know you're more complicated, I know you're smarter, I know you're more interesting than this.

She says “In the summer of 2006,” this is when she met him. “I was still dating and using those relationships to figure out who I was. There were a few guys with big hearts and strong personalities. And I found myself changing to suit them. John wasn't having it. He told me he wanted to have all of me or nothing. He assured me he didn't want to make me into anybody else.” 

So what we're seeing here is like, he's kind of nagging her, right? Because he's saying like, you're so much more than this, but implicit in that is kind of like, well, the music that I've heard from you isn't really you. And like the public facing self, you're better than that. So he's already setting the standard for her that she hasn't reached. 

Sarah: And I know what the real you is, inexplicably. 

Mike: So she kind of falls for this and they start dating each other. Totally in secret, like no paparazzi. They'll sneak him into hotel rooms and he'll wear a hoodie and come in the back door of a hotel. They do this whole subterfuge thing for months.

Sarah:  That’ll be very fun if you're used to your marriage being a TV show.

Mike: This is also the period, remember a friend CaCee, who like is her moral center last episode? She quits. She stopped working for Jessica because she thinks that John Mayer is bad news. She's like, I don't like this guy. He doesn't seem like he actually like likes you that much. 

And then what becomes very clear, the pattern in her relationship with John is he's like weirdly obsessed with her. You know how Jessica used to do those proactive commercials on late night TV?

Sarah:  Oh my God. Yes. I loved those Proactiv commercials. I remember these very well. Cause she was like, here I am on tour and I'm like stressed and not eating the best food. And that was bad for my breakouts. And proactive has been so helpful. And that was maybe like my first moment of feeling like she was a real girl, you know, and I really liked that she allowed there to be pictures of her with acne on her face and was like, it's stressful to be a pop star, actually. Yes. I love those Proactiv commercials. 

Mike: And so did John Mayer, that's sort of how he had discovered her and had gotten weirdly obsessed with her.

Sarah:  Okay. So John Mayer and I were like both watching those Proactive ads in our individual bedrooms at one time. That’s weird.

Mike: Yeah. He starts like advising her on which clothes to wear. He'll take her shopping and be like, you should have this outfit. Like, this is more you than this other outfit. 

Sarah: I don't think that someone you're having sex with should be in charge of your outfits. Like that could seems like crossing the streams. 

Mike: This is what she says, “The connection was so strong that he made me feel seductive and he spoke about sex and my body in a way that made me feel powerful, at least physically. His focus on me was the opposite of my marriage”. I think this is like extremely typical that after a long relationship, you end up dating somebody who is the exact opposite of it, and that’s what’s appealing. 

Sarah: Yeah. And that's how you kind of triangulate what you actually want.

Mike: And so she says “I would get up to go to the bathroom and John would ask, where are you going? When I was married, my ex-husband couldn't be bothered to figure out what city I was in. It felt safe to be so desired.” I like that she puts us in here because it shows how much self-deception she was going through at the time. Because he's so obsessed with her, she says, “I knew John would never cheat on me. And that confidence was a new feeling for me.” It’s very typical, this idea that like, this guy's really into me after like a really short period of time. So like, he must not be capable of ever hurting me. But there isn't like the next leap of like, if he's this obsessed with me after two weeks, who else has he been obsessed with after two weeks?

Sarah: Or like, what will happen when I'm not the shiny new conquest? You know, and after he's like taken down his tent and left the campsite.

Mike: And she mentioned later telling a therapist about this. She's like this is the form that our love took, blah, blah, blah. And then the therapist is like, you realize that's not love, right? That's obsession. Like loving somebody is mutual. It's not this, like putting them on a pedestal and not dealing with the person that they actually are.

Sarah: And getting stressed when they go to the bathroom.

Mike:  And so she talks about how almost immediately she's just constantly falling short. That he's building up this perfect version of Jessica since, basically the one that he's seen on TV, right. Where she's wearing makeup, the lighting is perfect. She's just like perfect sexual fantasy for every American male.

Sarah:  She's irresistible, one might say. 

Mike: And he's comparing that to the reality of her. This is what she says, “Where I felt insecure in the beginning was that I always felt I was falling short of the potential he saw in me. I constantly worried that I wasn't smart enough for him. He was so clever and treated conversation like a friendly competition that he had to win.”

Sarah: Okay. Has John been reading The Pickup Artist at all? Like, does he wear an ostentatious hat at times?

Mike: And she's talking about how his mouth goes as fast as his brain. He's very smart. He's very insightful. He's very funny. And she says, “When I tried to leap in and say something to add to the dialogue he was having with himself, he would challenge what I said, because that's how we saw the give and take of conversation. Sometimes he wouldn't let go of questioning why I thought a certain way until it had me second guessing myself. I’d get quiet, take another sip of alcohol and another, and wonder why I couldn't just sit on the couch with him without getting so anxious.” 

So this is also this thing of like conversation as like sparring and that when somebody says something you're supposed to sort of dissect it, like at one point she brings up Jesus and her faith. And he's like, well, why do you believe in the Bible? Who wrote the Bible? Where is it from? And it's like, all those arguments have been done. We all know the arguments for and against like literal religious faith. 

Sarah: Yes. Well, it feels like this worldview, and this reminds me of people who love to debate and I feel this is a very adolescent male kind of a thing. And kind of like Ben Shapiro like, where you're like, I'm going to debate you and I'm going to grind down your arguments. And I'm going to say as many things as possible and overwhelm you and win. And it's like, okay, you can do that, it's your life. But like, could conversation be more constructive if we didn't view it as a zero sum game? And also, it's stressful to be in a relationship with someone who's acting like you're deciding who should be Vice President.

Mike: Yeah, yeah, yeah, exactly. And it's also, it's placing the moral value of truth above the moral value of kindness and grace. 

Sarah: Yeah. That's you're, you're so smart. I like you.

Mike:  I mean, I feel strongly about this because I was one of these people for much of my life. So like this shit rubs me the wrong way because I see myself in it.

Sarah: Were you Jessica or were you John Mayer?

Mike:  I was John.

Sarah:  I also was definitely once John Mayer. Yeah, it was not a cool time. 

Mike: I actually remember I was riding a train in Spain and I heard people speak English in the sort of seat next to me. They were American. I was American, so we ended up chatting. This is like a weirdly indelible memory for me. After like an hour, one of the people was talking about like, I don't eat octopus, it's a smart animal and they're cute. And so I don't eat octopus. And then I did my like reply guy thing of like, well, by that logic, there's other animals, like pigs are also intelligent and like other animals have those features. And there was like this long pause and he goes, everybody gets to have one dumb thing. It shouldn't have been, but it was like this huge revelation to me that you can just like, let people have their things and not try to take it away from people like, who fucking cares if this guy doesn't eat octopus.

Sarah: Right? Like, why is life going to be better if they eat octopus? Yeah. And also, like, I think it reflects our own insecurity. Because if I'm going through life being like, all of my opinions and beliefs are logical and they're based on a reasonable assessment of facts, it's like, okay, that's not true because I'm a human being and not a computer that plays jeopardy. But if I want deeply to believe that about myself then I can also try and impose that on others.

Mike: Yeah. Yeah. And I also think it's really important that Jessica says he's making her anxious, which implies that it's not like, I mean, healthy debate is part of any relationship, but the fact that it's sounding to her like this is everything she says. 

Sarah: And if you're stressed to hazard an opinion, cause you're going to get grilled about it. And so you're like, I just won't talk about it because I don't have the energy for that right now. 

Mike: As if every statement you make has to be like a fucking PhD defense, well, what evidence have you marshaled in supported of that? Like, sometimes you just want to say stuff.

Sarah: When you're at home.

Mike: So this is their first of many breakups. Where after a couple of months, someone on her team leaks the relationship to the tabloids. John Mayer, like however famous he was, he wasn't as much of a like paparazzi darling. And then all of a sudden overnight, it's like, he's, he's, he's in the orbit of Jessica Simpson who has these paparazzi everywhere. And it's like, Oh, I guess John Mayer is on our radar. So they start following him to his house. 

Sarah: He's become part of the Jessica Simpson cinematic universe. So he has to be tracked now. 

Mike: And so it becomes this huge inconvenience for him. What's also really interesting is that him being linked to Jessica Simpson publicly, remember this is still 2006 back when there was like a big divide between pop music and like indie credibility.

Sarah: Oh, I remember this. This was kind of like when John Cusack and Meg Ryan were dating, it was like, what? Two people from like adjoining Hollywood principalities that we think of as touching, but not intersecting?

Mike: And so, I think a lot of his anger is partly because like he's now associated with this pop star who's like very uncool. Like Jessica Simpson was on a reality show, right? She's mostly known for this chicken of the sea thing. And so partly because he's irritated by the paparazzi thing, partly because he's losing his street cred. He breaks up with her in an email.

Sarah:  Oh shit, John, come on. If you're going to be all obsessed with someone at least break up to their face.

Mike: What begins now is a pattern of him breaking up with her by email and then seeing her in the press. And it boosts her credibility, or it reminds him how attracted he is to her. And then he'll reach out and be like, “Oh, I saw you on the Today Show yesterday, I just want to say, I've been thinking about you and like, here's a song that reminds me of you.”

Sarah:  Jessica, Jessica. I hate this.

Mike: It’s intense when they’re on and intense when they’re off. So when they're dating, she says he takes photographs of her constantly. He's like always kind of looking at and touching her body and being like, “I love your pelvis. And I love your elbows and I love your wrists.” And like, just rhapsodic. 

Sarah: I Don't like this.

Mike: Then when they're not together, he's like grilling her of like, well, were there men at that party that you were at? And like, wasn't this a guy that you dated before and do you know him? How do you know him? She says, “When he tapped me dry, he looked at me like I was withholding something. He would tell me that my true self was so much greater than the person I was settling on being, like there was some great woman inside of me waiting to come out and I had to hurry up and find her because he wanted to love that woman, not me.”

Sarah:  Yeah. That really sucks because it's like, it can feel like something positive. It can feel like someone's like, I just want you to be your best self and to grow and to not be this like phony thing that you're pretending to be. And you're like, I might be the phony thing. Like you really shouldn't date people if you're going in and you're like, this person has good bones, but they're a, fixer-upper and I’ve got to change some things, you know, I got to move this load bearing wall, but it's going to be good.

Mike: And so she says, because you know, this is only her, what second, third serious relation. 

Sarah: And the only one that she hasn't started as a literal teenager.

Mike:  Exactly. She's not really seeing the, just like wall of red flags, like the red sky above this relationship.

Sarah:  I have never loved or identified with Jessica Simpson more than I do at this moment. I'm just like, I'm there. I get it. I see it.

Mike: I get it so hard. 

Sarah: Sometimes you see all the red flags and you're like, Oh, this is fun. It's like a theme. 

Mike: And so in one of her emails to him, she says, “I promise to be myself. As I searched to become the woman you already see.”

Sarah:  John. I don't like that. That's just like if you're dating a cult leader.

Mike: It's bad. So they're breaking up and getting back together. A lot of their relationship takes place, it seems like over like long text message fights and like long email fights.

Sarah:  That's really bad. 

Mike: One of the things, the patterns that emerges, and this is also, it's so petty, but it's so infuriating, is that he'll like, I guess, correct her emails, or tell her that she's like a bad writer or not expressing herself well. So she starts sending them to friends and family to have them fucking proofread her emails before she sends them to him. Cause he's going to give her shit because of like having the comma inside the quote or whatever. I think this is also very typical and very sad because she's in this relationship that is just a constant tsunami of stress and anxiety. Like just being around this person, she's getting like a fight or flight response. She starts using alcohol to mask her anxiety because she's so nervous about being around him that drinking more is the way to deal with it. And so eventually he starts giving her Xanax because he notices how much he's drinking and he's like, oh, don't worry about it. Xanax does the same thing, but like it's easier to manage and people can’t smell it on your breath. We're going to take a slight detour now. Are you aware of Taylor Swift, a young woman named Taylor Swift?

Sarah: I am aware. I am aware of Ms. Taylor Swift. Yes.

Mike:  Are you aware that she also dated John Mayer? 

Sarah: Yes. I am aware that she dated John Mayer, and I am aware that the stone-cold bop We are Never Ever Getting Back Together, is specifically about him.

Mike: Oh, I only thought she wrote one song about him, Dear John, which I am now going to read to you. So here’s the lyrics, “Long were the nights when my days once revolved around you. Counting my footsteps, praying the floor won't fall through, again. My mother accused me of losing my mind, but I swore I was fine. You paint me a blue sky and go back and turn it to rain. And I lived in your chess game, but you change the rules every day.” That's great. John Mayer, of course, is asked about Dear John. And so he says that it humiliated him and that he's really mad about it. And so this is what he says, “I will say as a songwriter that I think it's kind of cheap songwriting.” 

Sarah: Oh my gosh, John. Just say your feelings are hurt and move forward.

Mike: I know she's the biggest thing in the world, and I'm not trying to sink anybody's ship, but I think it's abusing your talent to rub your hands together and go wait until he gets a load of this.”

Sarah:  Uh huh. I don't think she was doing that.

Mike: Also as someone who's like, all of his songs are like working through his own issues with relationships, to be like, you know, it's pretty rude to write songs about real people. It's like how many of your songs are about Jennifer Aniston. Like, should we go through the catalog? 

Sarah: I think we have this thing of wanting to rob women of their creativity by being like, well, she's just trying to get back at her ex. And it's like, so does it matter if like, you know, if that is some of the motivation potentially, like if it results in like a beautiful pop song that millions of people can enjoy, is it just that artist intent, John Mayer?

Mike: So back to Jessica and John, this relationship has many rock bottoms. But the bottom-est is probably what is about to happen next. So there is some sort of tribute to Dolly Parton at the Kennedy Center. You know, they do these things like Kennedy Center honors, where they get like a bunch of artists and they all sing like a different Dolly Parton song and Dolly Parton is there and she's clapping, and it's this thing like Dolly partner's dope. Here's like a celebration of her dopeness, right? 

Sarah: Yeah. What could go wrong in this festival of positivity? 

Mike: So Jessica is invited, she's supposed to sing 9-5. I know like the best karaoke song. So the day of this thing, she's there, it's like 11:00 AM. There's gown fittings and rehearsals and lighting and all this kind of stuff. She has to be there early. And so he breaks up with her by email at 11 am that morning, like when she has to perform that night.

Sarah:  Oh my God. Just wait until the day after the thing, John Mayer. 

Mike: And then he does the thing where he then sends her a song. So he breaks up with her and then like an hour later, he's like, I just want you to hear this. And it's a fucking Aerosmith song. It just begins the cycle where she's like, obsessed. Like, what did I do wrong? What is the encoded message in this song? Like, this is not healthy. 

Sarah: Yeah, but it's like she's in her own personal DaVinci code. And this is the clue that has been given to her.

Mike:  So she's basically a mess. She shows up at the Kennedy Center. One of the first things she sees is Shania Twain, who's like doing vocal warmups and stuff. And she notices that Shania Twain seems nervous. Like she's got stage fright because Dolly Parton is going to be there. You're singing a Dolly Parton song in front of Dolly Parton. And so Jessica sees like, if Shania Twain is nervous, how big of a deal is this? And so this kind of gets into her head and at one point her mom says, “You need not to be drinking right now”, because she's never gone on stage drunk before. 

And one of the ways that she copes with all of this anxiety and emotional turmoil and professional turmoil is to drink, to steady her nerves. And so she notices that like, by the time it comes to the show, she's like, Oh fuck, I'm kind of drunk. And so she tells herself like, whatever, I've gone on stage with, you know, with a cold or whatever. And then the adrenaline kicks in and it's fine. So this'll probably be fine. And then right before she goes on stage, John calls her and he's like, “Did you get my email? I just want to talk.”

Sarah: John, God! Like you broke up with her, just like break up with someone and then move on or don't break up with them and then keep bothering them if you're still having a relationship. Those are your choices. Like you inspired a mini wave of great pop songs about breaking up with you for a reason.

Mike:  I mean, this is basically what she tells him. She's like, if you're going to break up when they break up with me, but don't like break up with me and then send a fucking song to decipher and then call me to like talk about it.

Sarah: You are negatively affecting Dolly Parton right now. Like, do you want that? 

Mike: And so in the midst of this, she goes on stage. She gets through, kind of gets through the first verse and then she just starts like stumbling over it. And in the middle of nine to five, she just stops. 

Sarah: Oh man.

Mike: There's thousands of people there. The fucking President is there. The cameras are there, and she just stopped him on the song. And she says, “I'm sorry, it's an honor to be here, but this song is too good for me. I'm too nervous.” And she just walks off the stage. 

Sarah: That is like the most Jessica way to break off a performance.

Mike: It's like the opposite of a neg, she's like complimenting Dolly Parton as she's like running away, ‘it’s too good’. And so she goes backstage, the producer says, this isn't live so afterwards you can rerecord it. We'll fake it and put in inserts of the audience and like audience sounds and like, no one has to know. So like, this is still fixable. So as she's backstage, Dolly Parton comes down and of course Jessica is like mortified. Like I fucked up your song in front of you. You're like taking time away from this performance to come down and see me. And so the first thing Dolly Parton says is, “So I hear you're going to sing that song again. Before you do, I just want you to know that I wrote that damn song and even I don't remember the words.” So she's like, it happens, you're having a bad day.

Sarah:  I love this trend of like Jessica ending up in these horrible relationships and then like receiving these momentary, like shining words of wisdom from like country legends.

Mike: I know! And then she gets back on the stage. The band is there, the audience has gone. It's just her. And she still can't do it. She's too drunk. She's too emotional. She's too mixed up. 

Sarah: She's been broken up with John Mayer too many times. 

Mike: And so this performance and it's errors and they just like, she's just not on it. So like, nobody really knows about this, although it does leak to the tabloids. The footage of this incident is online because I think it like air on Canadian TV or like it aired live on some backstage, feed something, something. I could not watch it. I got 30 seconds into it. It's really painful to watch. She stumbled. She's got her hand over her stomach. And sort of, you can see your hand shaking and she's holding the mic and it just sucks. It just sucks to watch, and I couldn't watch it. And then she cuts to like a couple of months later. And she's just back with John again. 

I feel like the whole, like the myth of the rock bottom depends on this idea that like, things get so bad, and then like I had this epiphany, and I was done. But it's like she has the epiphany, but then she falls back into her old patterns, which is a very typical thing that people do. And then this is, this is just a rich text. “We went to Sony's Grammy after party together and I was so happy he posed for pictures with me because Grammy night is like the prom in our industry. He was nominated for five awards and won two. He broke up with me that night at the four seasons in Beverly Hills. I can't even recall why. I just remember knocking on his hotel room door and begging until he finally took me back in the middle of the night.”

Sarah:  Oh my God. I mean, I feel like there's something that to me seems very understandable about being drawn to a relationship with someone who like, intermittently accepts or rejects you, you know, because like that can be a way of proving to yourself that you don't deserve to be fully accepted. You aren't worthy. You aren't good enough to sing Dolly Parton's songs. The siren song of bad relationships is really hard to not hear.

Mike: Yeah, there is, I mean, there is this really addictive quality to relationships like this in ways that like, I don't, I don't understand, even as I've been in those relationships. I’m not, I have been Jessica before, but I have no additional insight into the pattern that is going on. 

Sarah: I feel like the natural conclusion to the story is cause to all of us standing up and like a Spartacus radio rebel moment being like I'm Jessica Simpson. You know, like, I mean, she is offering herself as like, yes, I'm a pop star, but in my heart of hearts, I am someone who's historically drawn to bad relationships and like, what could make her more human? I really don’t know. 

Mike: Yeah. And so they finally, it's actually interesting, they've never done any music together. She has seen it as, it's something that she and Nick did together. It was a part of the relationship. It's something that she has very complicated feelings about and she just hasn't really suggested it because like, that's just not a part of herself that she wants to share with John.

Sarah:  And maybe it's the only part of herself that remains sovereign in this relationship.

Mike: But then he starts to get jealous of that. And it's like, well, why did you do it with Nick and not with me? And so he suggests that they make a sort of remix, like she's written this song, that's on one of her albums, but he wants to like, ‘well, let's do it again and I’ll produce it, I’ll sing on it’.

Sarah: I don’t feel good about this Mike,  I've got a bad feeling about this. 

Mike: And so they get into the studio and she's too nervous to sing in front of him. And then he of course starts kind of like yelling at her like, ‘well, why can't you do this? Like, we've been planning this.’ And so eventually she just runs out and goes back to their hotel room and he comes back to their hotel room like hours later and they just never talk about it.

Sarah: Wow. And do they ever try and do it again or just like move on?

Mike: They just move on. 

Sarah: I'm excited for Jessica to try dating a non-musician. I got to say.

Mike: Oh well here we go. You're going to like this. So after this event, John breaks up with her again, he doesn't say it's because of the studio thing, but it's like, I mean, who knows, who cares? Like he breaks up with her again by email. So she starts dating a guy named Tony Romo, who was a quarterback for the Dallas Cowboys. And so apparently, he had like run into her dad at some event or something and had said like, “Hey, you know, like I've always been really interested in your daughter. Let me know if you could ever introduce us.” And her dad had brought it up to her and she says, she doesn't want to date people that are outside of the music industry. She says, “I believed I could only date people who could relate to me because they were in the business, which I guess was my code for, ‘I like emotional torture and fixing dark people’.” It's like, Oh, Jessica, she's been to therapy at this point. And like, she's very insightful about these patterns. And so this is actually quite cute. She's at home. She's at her dad's place. They're watching football, it's Sunday. And I guess it's the Cowboys playing. And after the game, you know, they're like, how'd you do in the game, like these sort of after game, sweaty interviews that they do with sportspeople. And so Tony Romo is being interviewed after this game. And so the interviewer asked him, ‘who's your dream girl’. And apparently, he just looks at the camera and he's just like, “Jessica Simpson”. And Jessica is like, “Holy shit”. 

Sarah: And the bat signal lights up the clouds.

Mike: And so, you know, they go out to dinner or whatever, they start dating. He is a Christian guy. He says the Lord's prayer before he goes to bed every night, which is like, good. She's found somebody who has like similar values to her and doesn't try to talk her out of her religion. This is also, this is. Well, we've had many surreal moments in this series, but this is by far one of the weirdest. Shortly after they announced that they're dating, she goes to one of his games. So she shows up in like his Jersey, but it's pink. And she's like in the luxury box or whatever. And apparently, he plays the worst game of his life. And then the jumbotron cuts to her toward the end of the game. And everybody starts chanting, ‘send Jessica home. Send Jessica home’ because they think she's a bad omen. They think she's the reason he's having such a bad game. 

Sarah: I mean, I feel like that's like the superstition that like women are bad luck on boats.

Mike:  I guess. Apparently, there's like a week's long debate on like sports radio and stuff about, should Jessica be coming to the games and how much should we blame Jessica for ruining her boyfriend's football performance?

Sarah: Couldn't he just like play a bad game once in his life? 

Mike: I know! And so she basically stopped going to his games because it's so controversial. There's also something really fucking funny that John Mayer writes a blog post defending her.

Sarah:  Of course he wrote a blog post. 

Mike: Yeah. He's like, she loves Texas. She loves football. She's not the problem. And it's like, John, shut the fuck up. Just stay out of this one, John.

Sarah:  Wow. He's like as a Jessica Simpson expert, I have to weigh in on this national conversation.

Mike:  And so other than not going to his games, it's actually like a relatively good relationship at this point. And one of the cutest details is that he is so into her music that like when she has friends over, he'll do the thing where he'll play her songs in the background and he'll be like, shhhhh, shut up, shut up. This is the good part. And like makes everybody listen to them. Which is nice.  It just makes me happy

Sarah: Yes. Jessica deserves a guy who's, you know, enthusiastically supportive of her. That's a good thing. 

Mike: So this is also the time, time when she actually starts working with Dolly Parton and she puts out a country-western album. 

Sarah: I didn't even know that.

Mike:  Me either. It was apparently number one on the country charts.

Sarah:  Which makes sense, because for what we've discussed, like that's what she's kind of wanted to do this entire time.

Mike: I mean this is part of like the transformation of her making music that she wants to make. Like her clothing company is doing well at this point, her last album has done well. She has enough clout that she can just be like, I want to make a country album, so I'm going to make one. And so she becomes like a modest star on the country circuit. She starts opening for Rascal Flats on his tour and she's like a working musician again, and she loves it. 

Sarah: It's so great. 

Mike: And this is by far the most outrageous detail. So at this time she starts to get hints. You're not going to believe this, that John Mayer is hanging out with her parents. 

Sarah: How did her parents feel about him? Because they didn't like him when they were dating. Right? 

Mike: So they actually really like him. They say he starts coming over because Ashley Simpson is dating Pete Wentz, who's in Fall Out Boy and he's friends with John, but then he just apparently just starts showing up. And so she talks to her parents. She's like, uh, it's kind of weird that you're hanging out with my ex while I'm dating someone else. And they're like, he comes over and like, he sits by this sort of fire pit at night. And like he plays songs for us and we all sing. It's kind of nice. Like he comes over and he, we did like a live John Mayer performance, like two nights a week.

Sarah: That's so weird. I mean, to be fair to John Mayer, that is innovative, I guess, because I have never heard of someone trying to get back into their ex's good graces by like, playing acoustic guitar for their parents every night.

Mike:  It's such a weird move, dude. But she also, she has a rule about this, that she's completely transparent about this with Tony, because she doesn't want to lie to Tony. And so he will still email her sometimes and she's like, Hey Tony, look at this weird email I just got from my ex. Like, she doesn't want to create the situation where it feels to Tony, like she's lying to him. But so one of the really interesting things is she's still sort of touring, but she's touring on like the country circuit. So she's a public figure at this time for like country music people, but she's, you know, she's not on a reality show. She's not putting up pop albums. So for most of the country, she's kind of disappeared. It's like, whatever happened to Jessica Simpson? 

And it's been a while since she's done things that the general population is really paying attention to. So she talks about, she's like touring things and one of their shows is at a chili cook-off like a state fair in Pembroke Pines, Florida. And so she goes to this event, she goes on stage. She has this great performance. The audience is loving it. And she's feeling like a bit of a comeback. Like I'm singing to crowds that really liked me. I finally found a form of music and a style that suits me and where I'm really appreciated. And after this performance, let me just send you, these are the headlines that show up in the press. 

Sarah: ‘Jessica Simpson balloons in weight.’ That is the headline I am seeing.

Mike: It’s bad. Can you read the first paragraph?

Sarah: Oh God. Yeah. Okay. “Jessica Simpson is one star, not afraid to supersize her meals. Jessica Simpson is one star, not afraid to supersize her meals after showing he's all woman at a country music gig in Florida, the one-time Brittany Spears lookalike stunned her male admirers as she stepped out on stage to show he's ditched her one time, 36, 24, 36, figure for a new set of curves.” It's so weird. It makes it sound like she threw her body out in like a fit of condo cleaning and then bought a new one. 

Mike: This is also, I hate this framing, because what you're doing is you're, you're making fun of somebody's appearance, right? This is eighth grade shit, but you're making it seem like you're giving her all the agency. Like she has decided to be a larger person now by eating supersized McDonald's meals, obviously. So it's like, you're trying to absolve yourself of moral responsibility.

Sarah: Also just  like all of the language is weird in so many ways. It's like, she's all woman now. And it's like, what was she before?

Mike: Also fuck this photo caption.

Sarah: Yeah. So the caption is, they have two pictures of her side-by-side and there's one of her performing in Florida, looking amazing, like wearing great high-waisted jeans and a big leopard print belt and a tank top. And then next to it is her and a tiny pair of shorts, you know, just like the, the like real thin Jessica that we recognize from Newlyweds. And the caption is proud “Jessica shows off her curves, left in her slim heyday.” Her slim heyday. Oh my God. It’s like, yeah, knows what her heyday was. I cannot fathom like, if you have kind of pulled yourself out of, you know, this terrible thing here is relationship with your body. And, you know, imagine if you're able to cultivate a healthy relationship with yourself and then the media weighs in.

Mike: And this is, I mean, we're not like that much better now. But we were really bad then. So the New York Post gives her the nickname, ‘Jumbo Jessica’ and apparently fashion magazines are running spreads about how not to look like her, to not have a belt up high, to not have quote unquote mom jeans. She becomes like a fashion don't. She decides not to sort of do the apology tour about her weight or like address it. This is what she says. “I decided I wouldn't tell anyone that the jeans were a size 25 waist, which is an American 4, I wouldn't go on talk shows to say I was 120 pounds when those photos were taken. The fact that I was that skinny and that I was deemed overweight, still frightens me. No way was I going to go out there and turn on my sisters by saying, “Oh no, you're mistaken. It was the angle and the fit. I'm actually a size four.” And I like this that she says, “What would that do to my young fans who may have been a size bigger or 20 sizes bigger? My publicist Lauren got so many requests for photo shoots and sit down interviews to ‘set the record straight’. It seemed like negotiating with a hostage taker. If I disavowed having a regular body, nobody would get hurt, except everybody would get hurt. We refused the requests unwilling to play into the game of shaming women.” 

And so by the standard of celebrities, she's actually pretty good. She's like, it's okay to be whatever size you are and I'm not going to defend myself. And she's not like, Oh, it's mean to call me fat because I'm really skinny. She's like, no, don't mock people for their looks and their weight, regardless of what they look like. Fuck you.

Sarah: Well this was like, I mean, yeah. I mean, just like if you, if you take the bait and are like, no, no, no, don't worry. I'm not this thing that you are disproportionately afraid of as a culture, then like you're only strengthening that divide ultimately. 

Mike: Yeah. There's also a pretty cute TSA interaction where she's going through security at the airport and they sort of pull her aside, you know, these random screenings, they sort of pat her down and then the person who's doing the pet on recognizes her. And he's like, Oh, you're Jessica Simpson. She's like, yep. And then this TSA agent is like, you know, you're really not that big. And Jessica says instinctively. She says, “Thanks.” And then she walks away and then she's like, “Wait.” And then she turns back around and she's like, “It would be cool if I was though, just want to be clear. It would be fine if I was big.”

I think what’s really interesting about this and I think this is like a real issue on an intellectual level. She gets that like any size is fine. However, she gets really self-conscious about her body. She doesn't go on a crash diet, which she's really like proud of herself for, but she also says I added a black vest to my costume when I performed, just like my days of performing at church camps as a kid, when my body was continually scrutinized for the potential incitement of sin. It just makes her self-conscious. 

There's also this really gross thing where, she doesn't lose weight, but people take photos of her, paparazzi photos, where she looks like she's lost weight. So all of these stories start to appear in the tabloids about how she went on a crash diet and she's lost like 10 pounds in two weeks. 

Sarah: So her weight is like a conspiracy theory, almost. It's like, you just see whatever you want to see. 

Mike: There's these like before and after photos of her performing in Florida and then like, whatever, her getting out of a car at some fashion thing in New York. And she's exactly the same weight, but they're like Jessica stopped eating carbs and she's at her new weight. And it's like, no, I'm not, I'm not getting into this stuff, but it looks like I am. The media is still sending exactly the same message, you've been criticized for your weight, therefore you lost weight. So in his defense, her boyfriend, Tony is actually great about this. 

Sarah: I should certainly fucking hope so.

Mike:  I know like by the standards of Jessica's love life, it's like, okay, great. Like somebody is not a complete asshole. So he's like, I'm attracted to you. You're beautiful. I don't care what anybody else says. But then he also, he also gets really controlling about other things. So this relationship starts to sour when she starts to realize that like he wants her to be this housewife, just like Nick did. The other Dallas Cowboys have these wives that like, that's kind of their job is to look after the house, look after their husband and like be there. And then Jessica is running like a $200 million company. She has a pop career. She also has an acting career at this point, and he like starts to get a little annoyed that she's doing all this independent stuff. And so one of the weirdest conditions that he puts on this, he says, you know, I want you to have a movie career. I want you to keep acting, but. I don't want you to do any movies where you kiss a guy. That's a line too far from me. And so, I mean, I think this is very interesting about masculinity, that it's not necessarily that he would be jealous, but it's how he would look to other dudes. That like, he would start getting teased by the other guys on the team. They're like, Oh, your wife is in this movie and she's kissing like Luke Wilson or whoever, which is just a weird, it's like a weird dynamic. 

Sarah: Well, it's showing who's more important to him as part of his social world.

Mike:  And also that, that is more important to him. Then his girlfriend's career, right? Because she mentions, okay, I'm like a 26, 27 year old, beautiful blonde actress, no kissing? Like what movies am I going to be doing where there's no love interest? This rules out every romantic comedy, even action movies will have a kiss in them. What movies can I do? 

Sarah: I mean, the first thing that I thought of was like some kind of an Erin Brockovich thing. And then I was like, even in those movies, you have to have a boyfriend or husband figure who's like, you're helping the disenfranchised too much and there's not enough time for me. So yeah. There's no options for her. 

Mike: Right. So she kind of decides to break up with him, but she hasn't sort of like made it happen yet. She's just kind of like in the unhappy thinking about it sort of stage, and she also finds out that John Mayer is making a more deliberate effort to get her back. So he's apparently this is part of his pattern. He sees there's a Vanity Fair story about her that has these beautiful photos from Mario Testino. So he gets obsessed with her again and starts hanging out with her parents more and being like, “Can you talk to Jessica for me? I just want her to know that I've changed. I'm a lot more mature now.”

Sarah:  This is so weird.

Mike:  It's weird, dude. He also does a thing where at her birthday party a party at her parent's house, he does a thing where he like stands up and he's like clink, clink, clink, clink, clink, and gets everybody to be quiet. And he's like, I just want to say I'm here, Jessica's here. And I just want to ask Jessica, will you take me back?

Sarah:  Don't ask women that in front of people!

Mike: It’s literally hostage chicken. It's like the worst.

Sarah:  I do not like it.

Mike:  But then what is actually really cathartic is that he does this in front of all these people. And I guess she's just like, ah, I have a boyfriend I'm living half in Dallas. Like this is wildly inappropriate that you would do this. So.

Sarah: No thank you. 

Mike:  But then what's weird, she goes back to Dallas and this is like a rich text. I'm going to ask you, do not respond to this until I'm finished. It's two sentences and there's so much going on in this. “On July 9th, the night before my birthday, Tony went through my phone. He saw an email from John to me, something about not being able to get a shower door to work at my parent’s house.” Okay. You can respond. 

Sarah: Okay. That’s so weird. Why is he emailing her? What is this fixation? What horcrux have you turned this poor woman into?

Mike: And I love that he's emailing her about like the dumbest shit. First of all, why are you taking showers at her parent’s house?

Sarah:  And why do you think she'll know how their shower door works? I mean, I kind of am pleased by the sort of the like lack of dignity implicit and that level of desperation, but like I'm more annoyed still.

Mike:  And then you’ve also got the additional layer of Tony going through her phone and reading her emails from John, which is like, ah, don't do that. 

Sarah: Don't do that. Don't go through someone's phone.

Mike: And he confronts her. He's like, why, why is John Mayer showering at your parents' house? And she's like, I don't fucking know, this guy sucks. Like I didn’t invite him to the shower. Like, I haven't even answered this email, but he doesn't believe her. And then she didn't tell him about John Mayer's weird clink, clink, clink thing at the birthday party. Cause she thought it would be awkward. Like for whatever reason she didn't tell Tony. And so he asks her like, have you seen John Mayer this week? Yes or no. And she's like, yes. Which sounds like she's lying. And then he basically blows up at her and breaks up with her. 

Sarah: Oh my God, that sucks because it's like, she's being punished for John Mayer's behaviors.

Mike: Yeah. But then also it's good because Tony kind of sucked. And apparently after Tony realizes after like a week, I haven't heard through the grapevine that she's now dating John Mayer. So like, maybe she wasn't cheating on me with John Mayer. 

Sarah: Maybe she was telling the truth about not wanting to get back together with this horrible ex she had, that was horrible.

Mike: This horrible man. And he then tries to get her back and she's like, nah, you checked my email on my phone and you didn't believe me. You weren't a good person to break up with and that's pretty revealing of your character. And so I don't want to get back together with someone who breaks up with someone in that way.

Sarah: Right? I mean, people do you a favor by showing you how they react to being in a little bit of hot water. 

Mike: And so this is like rock bottom, number 12. After she sends Tony away permanently, she then drives over to John Mayer's house. And she's like, well, he's been pining to get back with me. I guess the universe is telling us that it's time for me to give in.

Sarah: I think that the universe often is telling us to do whatever weird cultural message we have absorbed into our brains, unfortunately, and that might be what the universe is. 

Mike: And then extremely predictably, she shows up there and she's like, “Okay, let's give it another shot.” And he goes, “Eh, I'm not really ready. I don't know if I want to do this.”

Sarah: Oh my God. John Mayer. 

Mike: I know I'm making the most flamboyant vaffanculo fingers, right now, waving in the air. 

Sarah: It’s just like, just stop. It's funny because it's like, I know that people are constantly engaging in behavior where like, on some level they're like, this is a bad idea. Why am I doing this? And, and yet they don't stop. So like, it's not like it's surprising when people do that at all, but at the same time, I'm just like, John, do you see, do you see what you're doing?

Mike: Yeah. And then this is super fucked up. So he has just come up with a new album. He insists on making her listen to it. This is like this horrible pattern in her life. They're listening to the songs. He's like, I wrote this one about, you know, and then she doesn't say this in the book, but I think it's Jennifer Aniston. She's like you were also dating Jennifer Aniston at the time. How do I know this song isn't about Jennifer Aniston? He paused and told me he could never find material to write with her. So I'm material to you? 

Sarah: Yeah. And like, fuck Jenifer Aniston.  And she doesn't inspire my music.

Mike;  It's like, It's again, just like the perfect neg, right? It's like, you make me want to write music and it's like, that's not really a compliment. It's not, that's not you. 

Sarah: Right. It's revealing of a worldview where your preferences are like the arbiter of quality.

Mike: And so,  this is again, you know, you have the epiphany. You're like, he's only doing this for material. It's absolutely disgusting. And then she stays with him for three more months. It’s like, okay. You know, she realizes what she's doing. She talks about it, very insightfully in the book. Like I knew it was dumb and bad and I did it anyway. 

And then what's really interesting is what actually does it, what really breaks them up and like puts a stake through the heart of this relationship once and for all is his fucking Playboy interview. Where first of all, he says appalling stuff about black women. And he says the N word, like not a great feature of your boyfriend. And then I'm going to read you this thing of what he says about Jessica Simpson. It's bad. Playboy says “In 2006, you began dating Jessica Simpson and the paparazzi started stalking you. Certainly you knew that was going to happen?” And then Mayer says, “It wasn't as direct as me saying, I now make the choice to bring the paparazzi into my life. I really said, I now make the choice to sleep with Jessica Simpson. That was stronger than my desire to stay out of the paparazzi eye.”

Sarah: Or to like, have a relationship with her. But whatever.

Mike: He also says, “That girl is like crack cocaine to me. Sexually, it was crazy. That's all I'll say it was like napalm, sexual napalm. Have you ever been with a girl that made you want to quit the rest of your life? Did you ever say, I want to quit my life and just fucking snort you. If you charge me $10,000 to fuck you, I will start selling all my shit just to keep fucking you.”

Sarah:  And you know that he thinks that he's like saying something nice. 

Mike: And also, she's like a Christian and she's a public figure and yeah. Well, she talks about when, first of all, it was just such a dehumanizing way to talk about somebody that you dated. Secondly, she knows she's a woman in public life. She is going to get asked about this for the rest of her career. And that is exactly what happens, for years after this, every time she sits down with an interviewer, they're like, what do you think about John Mayer saying your sexual napalm? 

Sarah: Jessica, are you sexual napalm?

Mike: It's like, this is going to be a huge pain in the ass in my life for years and it's going to sexualize me again when like I'm running a company I'm in my thirties. 

Sarah: John Meyer’s metaphors about women are also very weird. Like there’s the Joshua Tree Vagina, and then the napalm thing is like, why John Mayer, are you so interested in conceptualizing yourself as having no power in this situation? Like, what's that about? 

Mike: There's also the thing. I also think part of this, I have no evidence for this, but I think part of this is like somewhat performative, that when men talk about women to other men, they tend to oversexualize them because they don't want to admit that, like, we actually connected as people. Like you can't say that as a man in public life, or maybe men don't say that as men in public life.

Sarah:  Maybe if one brave man starts doing that, then others will follow.

Mike:  But it's like in his like little like marmot brain, he's just like, Oh, well, like I really like fucking.

Sarah:  And I loved having sex with her. And it's like, John, you could say the same thing about a pumpkin. Like, what does it mean. 

Mike: So he writes her a letter to apologize. I wish she, I wish she printed the text of it. I'm sure. It's funny. We don't know what it does. 

Sarah: I bet there are grammar mistakes in it too, which would be highly satisfying. 

Mike: And then she completely ghosts on him. She says, I love this line, “I was done with this man in a way I never thought was possible.”

Sarah:  I was like, we are never, ever getting back together. I love that John Mayer inspires this response of like, I am done!

Mike: Like the done-est. 

Sarah: Like blow up the building. Like, let's use some of my sexual napalm on that. 

Mike: She also says she's like so done with him, she changes her number and her email address. If you're somebody like Jessica Simpson with like a million contacts, it's actually a huge hassle to do that. It's like, that's how much she wants this man out of her life. 

Sarah: That's beautiful. And it's nice because it's like, she's like had all these relationships that have gone wrong in various ways. But like this one is like, maybe so flamboyantly bad that it's allowing her to like, be like, goodbye to this whole era of my life. That's my dream. 

Mike: And so that is where we are going to start to wrap up the story of Jessica. As you mentioned earlier, one of the things we really like about the story, as opposed to a lot of our other episodes is like, we know that everything sort of works out for Jessica. And so I think we should end with a couple little montages of how things ended up working out for Jessica.

Sarah: I love that, let's do it. 

Mike: So six months after the John Mayer ghosting, she meets her current husband, Eric, who is a football player for a team. And then he retired in 2008 and there's this whole sort of complicated grid, flowchart thing, of like how he ends up at her house. It's like a friend of a cousin of a friend of an employee. But anyway, she's having friends over to watch, I think, a football game ,or maybe a basketball game, like having a bunch of buddies over on like an afternoon. And he shows up, this hot, retired football player. And I really like this, he kind of walks in, you know, to meet the host of the party you're going to, and he walks into the kitchen and she's chatting with a friend and he says, hi, I'm Eric. And he sees that sort of next to her in like the little kitchen Island thing is a book on dream interpretation. And he also notices that it's dog ear and there's a million post-it notes in it. And like this thing has been like loved to death. And so I really liked this about him, that he completely skipped small talk, like no traffic, no weather, and just goes to like, I guess you analyze your dreams. And she says immediately, she's like, yes, I do. Last night. I dreamed that I pooped out a pig and he's like, alright. And then they just sort of instantly clicked. And I guess they sit sort of like in her little kitchen nook on the steps, they just sit shoulder to shoulder and just talk for like two hours. And then as people start to trickle out of her party, he's like, well, better get going. And she's like, stay. And so he spends the night he has to leave early the next morning to go to a Marianne Williamson seminar, which is like a nice little cameo. And so throughout the rest of the book, it's just the experience, over and over again of dating somebody who casts her as the protagonist of these stories. So she has like a thing. She's not sure where it came from, but she has this like fixation on 11:11, like the time.

Sarah:  Cause that's when you make a wish in my understanding, right?

Mike: Yeah. Yeah. He proposes to her on November 11th at 11:11 AM.

Sarah:  That’s adorable.  And he's like, you like this and I have noticed.

Mike: It's just a way of being like, I'm going to make this story special for you. Like I'm not, I'm not casting this as like, I'm going to have this amazing proposal story, like jumbotron style. It's like, I want your feeling of specialness to be central to this. She also, one of the things that she actually sort of writes around in the book and I completely understand, is her relationship with her parents. That's something that she never goes into detail. Her description of firing her father is one paragraph. She basically says that her parents get divorced in 2012. She kind of chooses her mom's side. She doesn't see her dad for a while, but he's still her business manager. And he just starts making more and more erratic decisions, apparently. And people we'll say to her like, oh yeah, I thought we had this deal, but then you pulled out at the last minute and she'll be like, what? I've never even heard of this. And eventually what she says in the book is just like, I had to go forward without him. So, you know, she thanks her dad in the acknowledgements, they're still close. I get why she did it, go into it too much. But so that's really all we get of that relationship. She also talks about, you know, sort of running up to this intervention that her friends have in 2017, that she's drinking more. She starts getting more anxious about her body after she has two kids, she decided to get a tummy tuck. She goes into the doctor and the doctor says, I can't do this because there's too much alcohol in your liver and too many prescription drugs, it's not safe. And so I think she just finds another doctor and gets it anyway. Apparently like her staff and stuff start marking the alcohol bottles in her house so they can monitor how much she's drinking. 

Then as we talked about in chapter one, she has this sort of breakthrough with her dad. She has a breakdown, she has an intervention. She starts seeing a therapist twice a week. She decides to stop drinking. Eric decides to stop drinking. And there's actually some really interesting stuff about, just sort of the weird life adjustment that has to happen after you quit drinking when she's built her life around alcohol in all these ways that she wasn't really aware of until it's gone. So like the first time she goes out to dinner and they don't order a bottle of wine, it's like, oh, I, I guess we can do that. Like, that's a little test. And the first time she performs without alcohol and the first time she goes to a friend's cocktail party without alcohol, it's just like all these little milestones of her life that had become inextricably linked with alcohol.

Sarah: I feel like alcohol is like a security blanket in that way, and it's like being Dumbo and realizing that you can fly without your magic feather.

Mike: And so she starts to sort of deal with her past and explore all this stuff in therapy and come to a lot of the insights that she's had throughout the book. And so the scene we're going to end with, she decides to sort of like a reward for everything going really well. She tells Eric that she wants to take her and the kids to Disneyland, even though like Disney is a weird place for her, right. Because of the Mickey Mouse Club and these performances that she was doing. And it's always been a site that like, she feels weird about.

Sarah:  Oh God, I mean, I can't have any personal baggage with Mickey Mouse, how stressful. 

Sarah: And so her husband's like, are you sure? And she's like, yeah, I'm ready. There's a scene. The night that they get there, they're at the pool at their hotel. They're playing around. This woman comes up to her. And says, Oh my God, it's Brittany Spears. And Jessica Simpson is like no, sorry. And so this woman thinks that she is Britney Spears, but she's like being coy, you know, like celebrities do that. Like I'm not Wilt Chamberlain. Like, no, it's not me. 

Sarah: This reminds me, Judy Greer has a book called I believe, I Don't Know Where You Know Me From, like, this is a common experience.

Mike: And so this woman is like, Oh, come on. Like we know it's you. We won't tell anybody else. We promise, it’s fine. Please just take a picture with us. We won't bother you anymore. And so it's easier. So Jessica’s like yeah. Okay. So whatever, she's like, smile, they're like, thanks Brittany. And they run away. She thinks it's funny. She doesn't really think anything of it. And then the next day she's like walking around Disneyland with her kids. And this woman from out of nowhere, like runs up to her and is like, Oh my God, it's you. And it's the same woman from yesterday who took a selfie with her, who thought that she was Britney Spears and she's like, Oh, hello again. And this woman goes. You're Jessica Simpson. I'm so sorry. We were looking all over the park for you today so that we could apologize. We finally realized it last night.

Sarah:  Oh my gosh. That's so lovely. 

Mike: And she's like, these things happen. It's not a big deal. And this woman says, Jessica, can we take another photo with you, as Jessica Simpson? And Jessica says, only if you smile. We’re ending with an anecdote with metaphorical significance. 

Sarah: That's beautiful. So we're leaving her at Disneyland, knowing who she is, which is where I hope that we all can be as soon as possible. 

Mike: Yes. So yeah. What do you, what do you think we're done. That's the end of our Jessica journey.

Sarah:  I love Jessica Simpson so much.

Mike: Oh my God. This has been so fun.

Sarah:  And I have loved getting the responses from people about the series, because we've gotten many responses that I've seen from people who were like, I did not think that I would become so invested in Jessica Simpson or that I would care, but I do. I know, you know, I mean, there's a lot of celebrity memoirs in the world, right. They really run the gamut and there's the ones that you can tell were kind of written by a team and don't involve a lot of self-disclosure. I think it's very meaningful and worth remarking on when someone claims to be telling you the story of their life and actually does, like, I feel like I have grown from this experience. Like I feel I identify Jessica in so many ways. I am a feelings addict. I am drawn to bad relationships. I have my own substance security blankets. Like I just feel very connected to her in a way that I truly never imagined would happen when she was being aggressively marketed to me as a tween. And I just really love that. I'm just really happy about that. 

Mike: Sometimes there's a person around the torso. Sometimes we can find them.