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Join Kristin Cavallari in this episode of Honestly Cavallari as she continues her journey on The Headline Tour. This installment delves into the challenges and triumphs faced during the tour, offering an intimate look into her life and career. Discover the latest developments and personal insights from the reality star.

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Transcript
00:00Previously on Honestly Cavallari.
00:08I'm more nervous tonight than I was last night.
00:11I have two shows back-to-back the same night in Chicago.
00:15The first show is with the season two cast of Laguna Beach.
00:17Talon and I dated before MTV ever came to our high school.
00:21And then my ex-boyfriend Mark Estes originally agreed to be on the second episode
00:25as well as Harry Jousey from Too Hot to Handle.
00:28Were we seeing some titties on that?
00:30Probably.
00:31Oh, yeah.
00:32But Talon decided to group text message on Instagram, both Harry and Mark.
00:38Okay, so Mark had no idea that Harry was coming.
00:41It was a huge blow to his ego, and he's not coming now.
00:45It is my fault.
00:46Yeah, you ruined my whole second episode, so thank you.
00:49Oh, my God, here we go.
00:50I'm so nervous.
00:51Someone told me that you have dating advice for me.
00:54I feel like you need to stop thinking with your chi-chi and more with your head.
01:00Just walk away like all my friends.
01:08I love you guys so much!
01:10Yes!
01:11Yes!
01:11Yes!
01:12Yes!
01:12Yes!
01:13Yes!
01:13Yes!
01:14Yes!
01:14Yes!
01:15Yes!
01:15Yes!
01:16Yes!
01:16Yes!
01:17Yes!
01:18Yes!
01:19Yes!
01:19VIP is supposed to start in, like,
01:21we got, like, five minutes to go to basketball.
01:23What time is it? It is 8.40.
01:25That was awful.
01:26I was out there like, this is so bad.
01:30What'd I do? I'm not trained media-trained.
01:33Do you need a minute, Kristen?
01:40Wait. Five minutes.
01:42This is the only stop where I have to do two shows in one night,
01:45and I'm pretty let down by Talon.
01:48Okay, these were hot.
01:50I know, I was like, dude.
01:51The show was like, like,
01:52hey, you should ask Kristen to prom.
01:54I'm like, oh, that sounds really terrible.
01:56I definitely... What the ?
01:58I'm sleeping in bed with Talon,
02:00but I was fully closed.
02:01We're all sleepy is what we were doing.
02:03We were.
02:04Was that true, Talon?
02:05You guys shut the up.
02:08It was horrible.
02:10No, you felt that way because I saw your face.
02:11Like, I've got a whole other show to do.
02:13I have to go change, do a meet and greet with 200 people,
02:16and then click in for an entirely different show.
02:19I couldn't concentrate because I was shaking.
02:21But with Harry, I don't know if I'll talk to you.
02:22Harry's gonna be great.
02:23I could talk to Harry for five hours.
02:25I'm so relieved that it's Harry that's my next guest,
02:28and I'm hoping that his just natural,
02:29positive energy is gonna bring me back up.
02:32Hey!
02:33So fun.
02:34So great.
02:35I think that's good.
02:36It was all done.
02:37We have a lot to talk about.
02:38Okay, yeah.
02:40So is Johnny?
02:41Yeah.
02:42He'll be in the audience.
02:43I'm gonna pull him up on stage for like 10 minutes.
02:45My ex-boyfriend, Mark Estes, dropping out of this podcast episode
02:48is tough because the whole theme of the second show
02:51is people who have been on my podcast before.
02:54But now I'm gonna be bringing up Johnny,
02:56my very first boyfriend from Chicago.
02:58I've talked about him a couple times on the podcast.
03:01We were as in love as you can be at the tender age of 13 and 14.
03:06Have you talked to him?
03:07Is he nervous?
03:08I think he's nervous because he's been like,
03:11wanting every little detail, you know what I mean?
03:14Which I, by the way, I totally understand.
03:16For people who don't do this, like,
03:18this is, it's nerve-wracking for me and I do this shit.
03:21So I even appreciate him even getting up.
03:24When was the last time you spoke to him?
03:25Probably like 15 years since I've seen him.
03:27He is in the middle of a divorce.
03:29Mm-hmm.
03:29Really?
03:30Yeah, when I told my mom that, she was like,
03:32huh, I know how these things work.
03:34I was like, no, no, no, no, no, no.
03:36I'm not gonna end up with Johnny.
03:38Guys, ooh, I lost my virginity, too.
03:39That's so crazy.
03:41Johnny was actually coming to the Chicago show anyways.
03:44I was like, wait a minute.
03:46This could be really fun.
03:47We all know how it is to get over your first love.
03:49It's very difficult.
03:51And I do wonder if I've sort of, like,
03:54changed the narrative in my own mind all of these years.
03:57But to have his perspective, I think, is gonna be awesome.
03:59But yeah, I'm excited.
04:00I have to go do a meet and greet right now.
04:03Oh, you're going to.
04:04I know.
04:05Let's have to go right back.
04:06I love you.
04:07I love you, too.
04:08Thank you, you guys, for coming.
04:10I love you.
04:11I love you.
04:14Oh, my feet run.
04:15I love you.
04:20Oh, my God.
04:21Hi, you guys.
04:22Hey.
04:22This is my outfit for the next show.
04:23Oh, I can't put my arms.
04:24Shoot.
04:25OK, I'm limited here in what I can do.
04:26Sorry.
04:27OK, normally I'd put my arm around you, but I can't move in this.
04:29So we're just snuggle up.
04:31But I can't move in this.
04:32I can't move in this.
04:33Normally, I'd put my arms around you guys.
04:35But I can't move in this.
04:39Hi, how are you?
04:40Talon trying to steal the show.
04:42I know.
04:43I'm all right down, bud.
04:44I'm glad that Talon's married for you.
04:46You're going to be a great couple.
04:49No.
04:51It's so nice to meet you.
04:52You, too.
04:52Have a good night.
04:53Yeah, you're right.
04:56After what happened with Talon, having to, like,
04:58turn it on and pretend like everything's fine
05:00is pretty difficult for me.
05:01OK.
05:02Bye.
05:03Holy .
05:05But I'm trying to just put this aside,
05:07let it go, and get back up.
05:09All right, here we go.
05:10I'm so happy to be home.
05:13All right, we're going to have some fun tonight, you guys.
05:15Do you guys like tall men?
05:16Yeah.
05:17Do you guys know the show Too Hot To Handle?
05:19I love him.
05:20Please welcome Harry Johnson.
05:21I love him.
05:22Please welcome Harry Johnson.
05:23I love him.
05:24I love him.
05:25I love him.
05:26Harry Johnson.
05:27Harry Johnson.
05:28Harry Johnson.
05:29I see a little bit of me in him.
05:31He's kind of misrepresented, too, because he has this reputation
05:35as sort of being like the playboy.
05:37We love him. Please welcome Harry Jousey!
05:43Harry Jousey? I see a little bit of me in him.
05:47He's kind of misrepresented, too,
05:49because he has this reputation as sort of being, like, the playboy.
05:53Just not the best rep, but when you get to know him, he is the sweetest.
05:58I'm not celibate because I want to be.
06:02Fair.
06:03No.
06:05Breaking it tonight.
06:05Yeah, yeah. Right now.
06:09Listen, I'm always open to flirting. Let's put it that way.
06:12What's up, buddy? How you doing?
06:14You look so hot.
06:15Guys, Harry is on a, on a, on a, I was going to say a kick.
06:19This is a, I don't want to say a phase.
06:20He's trying to become husband material, okay?
06:22I'm trying. I was trying to be celibate, but I keep relapsing.
06:26Who has been your favorite celebrity hookup?
06:29Oh, oh, no.
06:32He has to tell us, right, you guys?
06:34Chris, yeah, Chris is my favorite hookup.
06:39No, f*** off.
06:43Do you feel like you have underlying sexual tension with Harry?
06:47How do I want to answer this?
06:49Um, I, who's a celebrity hookup that we don't know about? Miley Cyrus.
06:59No.
07:02No.
07:04This is Let's Be Honest.
07:06I don't know if I, I don't know if I can.
07:07Here, whisper it in my ear.
07:08No, because you're Mike.
07:12Well, what else are you doing to become a husband?
07:18You know what I realized, actually?
07:19I realized that when I, I've got an avoidant personality.
07:23So when I start to like someone a lot, I'll text someone else.
07:26So that I don't like that person as much, and I'm not, like, addicted to them.
07:31You're self-sabotaging.
07:33No, I realized this before.
07:34Now I'm perfect.
07:36But, but before, I realized I would do that because I'm like, oh, I don't want to get hurt.
07:40But now it's like, kind of nice to get hurt, because you know you're going to be better after it.
07:44Oh, my God.
07:45Is that good?
07:46Did I do well?
07:47All the girls are crying.
07:49We love that.
07:50Okay, see, you are husband material now.
07:52It's working.
07:55You should take your shirt off right now.
07:56Have you seen?
07:59Have you guys seen his body lately?
08:02Is that only on Close Friends, or do you post that for the public?
08:05I actually sent her a nude, and she didn't like it, so whatever.
08:10Let's talk about it.
08:11Okay, let's talk about it.
08:12Okay, I got a dick pic from Harry, you guys.
08:23Okay, I got a dick pic from Harry, you guys.
08:27He came on the podcast.
08:29I was like, I love Harry.
08:30Like, we're like buddies.
08:33I wake up one morning to a picture from Harry on Instagram, and I had a feeling, you know?
08:39I was like,
08:39Was it like 7 a.m. as well?
08:41It was early, like morning wood.
08:44Yeah, I was up.
08:45I was ready to go.
08:45It was like up here.
08:48If you're trying to become a husband, is that the best move?
08:52Just rapid-fire dick pics everywhere.
08:55No, these are selective.
08:56Like, I've really thought about these people.
08:58Okay, I'm honored.
08:59I'm honored.
09:00What about you?
09:01Have you been getting...
09:01What?
09:02No!
09:02Have you been getting a dick down?
09:04Guys, who's been blowing her back out?
09:07Let's go.
09:08Come on, Kristen.
09:09Tell everyone.
09:09Oh, the last time I had sex was New Year's Eve.
09:12You're a liar.
09:13I swear on my f***ing life.
09:15I have sort of sworn off men for the last few months while I was prepping this podcast tour.
09:19What are you going to do to, like, to relieve stress on tour?
09:24Masturbate.
09:24I knew you were to say that.
09:28And now I got back on Raya, and I'm sort of, like, talking and dabbling, but I'm not planning
09:33on meeting the one at a bar in Chicago.
09:36Although they say that's when it happens.
09:39I literally was like, I'm preparing for my podcast tour.
09:42Preparing for my podcast tour, so I'm going to stop having sex.
09:44I would double that s*** up.
09:45I'd be trying to f*** three people a day.
09:47Like, we've got to give the girls a story.
09:48Like, we need some famous sausage out here so we can tell the girls.
09:52Who's the most famous guy you f***ing?
09:54There's a few.
09:59Wow.
10:00We've been busy for the last 20 years.
10:02I took 10 years off, though, obviously.
10:04You took 10 years?
10:04Well, I was married.
10:05Oh.
10:06That shouldn't slow you down.
10:08When you get married, will I be invited to the wedding?
10:12If you're objecting, for sure.
10:14I'm down, honestly.
10:16Harry, I love you.
10:18Love you, too.
10:19Am I out now?
10:20No, you're not done.
10:20You're not going anywhere.
10:21Get comfortable.
10:22Do you guys remember when I've talked about my eighth-grade boyfriend, Johnny?
10:28Who I lost my virginity to?
10:32He's here!
10:33Come on!
10:35Give it up for Johnny, you guys!
10:41You guys, honestly, Johnny has real balls for coming up here right now.
10:47Johnny being my first love, I really sort of, like, put him on a pedestal all these years.
10:52My parents got a divorce.
10:53My dad moved to Laguna Beach.
10:55And my mom was in a new marriage.
10:57At the time, I didn't feel like I was a priority.
11:01And Johnny was my stability.
11:04Like, Johnny was where I found connection.
11:06Also, you look the exact same.
11:08He looks the exact same that he did in eighth grade.
11:10It's wild.
11:10You look like this in eighth grade.
11:11With a beard?
11:12Not beard at all.
11:13He was being held back.
11:14I had a beard at 11.
11:15That's crazy.
11:17The heartbreak that I felt with Johnny, that me up in such a way that I can't even explain.
11:23And actually, that's part of why I was, like, the heartbreaker.
11:26I was, like, known as being the heartbreaker because I never wanted to feel that ever again.
11:30And that's to say, but it's the truth.
11:32Really, Johnny was impactful for me.
11:34Would you say that we were in love?
11:36What do you say?
11:43That's not fair.
11:45Yeah, for as love as you can be in eighth grade, I would say yes.
11:49I'd sneak into your room and then?
11:50I know!
11:52Thank God my mom left.
11:55So I would wake up in the morning, and I would have, like, poems on my window.
12:00You'd wake up next to me.
12:03Well, yeah, sometimes you would be there.
12:05But you would, like, come over in the middle of the night and put up, like, poems, and
12:08I love you, and I'd wake up, like, oh my gosh.
12:09That's the podcast version.
12:12It's true.
12:13I mean, we also did dirty shit, too.
12:15Tell us.
12:15To be clear, you would actually greet me in outfits just like this.
12:21It's very...
12:23It's...
12:24I saw you come out in this, and it's hard.
12:27It's really hard.
12:28What's going on in eighth grade?
12:29I mean, yeah.
12:30Oh, my God.
12:32Okay, but hold on.
12:36I want to talk about something.
12:38So I...
12:39We broke up, and the second I moved to Laguna, you hooked up with my best friend, Lainey.
12:45He me up!
12:47He's the reason I was a heartbreaker.
12:49So before you left, we broke up, and you were, like, sampling Barrington.
13:00That was what?
13:02Sampling Barrington.
13:03I didn't hook up with anyone in Barrington.
13:05Oh, you did.
13:05Name a name.
13:08You broke my heart, actually, because you hooked up with my best friend.
13:12Who?
13:14Who?
13:16Tommy.
13:17I don't even remember Tommy.
13:19Exactly.
13:21I hooked up with Tommy?
13:24Who the f*** just told me I'll break his nose.
13:26Holy s***.
13:26I didn't blame Tommy.
13:27I blamed...
13:28I hooked up with Tommy?
13:38Who the f*** just told me I'll break his nose.
13:39Holy s***.
13:40I didn't blame Tommy.
13:41I blamed...
13:42Wow, this did not go how I planned.
13:44Um, okay, fair.
13:47Well, I'm sorry that I broke your heart.
13:49I'm trying to take accountability for everything I did.
13:51You were always a heartbreaker.
13:52This narrative that it starts with me.
13:53Right, I guess it was me.
13:56Johnny is a massive letdown.
13:58It honestly breaks my heart, because for all of these years, I have held my relationship
14:03with Johnny in this high regard.
14:05And then he got up on stage, and he was a completely different person.
14:08But I really appreciate you coming up on stage.
14:12I know this is not easy.
14:13Of course.
14:13So thank you.
14:14You guys, give it up for Johnny.
14:17Woo!
14:18He was the only person that I gave the questions to beforehand, because obviously he doesn't
14:24do this stuff.
14:25Thank you guys.
14:26Thank you so much, Haley.
14:27Oh my God.
14:29He knew exactly what I was going to say.
14:31So to me, it just feels premeditated.
14:34Like he wanted to come out there and tear me down.
14:38I want you to come out, love!
14:41Thank you!
14:44These memories that I've had of Johnny all of these years now, he just completely ruined.
14:49I mean, quite honestly.
14:52How about Johnny calling me out?
14:54I hate him.
14:54What did he say?
14:55Wait, did Johnny come out tonight?
14:57Yeah, where were you?
14:59I didn't see that.
15:01Okay, let's get the out of here.
15:08So excited.
15:10Today is my only day off, and I've just kind of hit a wall.
15:14So we're going to get some IVs, magnesium, vitamin C, glutathione.
15:18Like, I need all the vitamins today.
15:20I need to just get my pep back a little bit.
15:23Wait, so you know how Harry and I, we brought up the dick pic.
15:28So this morning, this is the shit that I do.
15:30I sent him this picture.
15:32It's a lingerie photo that I sent all my guys.
15:34Oh, wow.
15:35And then he was like, let me know about New York, because he's going to be in New York when
15:37we're there.
15:37And I was like, oh yeah, come out with us.
15:39He goes, oh, we should have kissed.
15:41And I go, we really should have.
15:43There's still time in New York.
15:45He goes, wait, are you ovulating?
15:46Why the change of heart?
15:47I go, I woke up horny.
15:51Oh my gosh.
15:53I didn't sleep in your room.
15:54What are you doing?
15:56And then he goes, f*** my life.
15:57Catching the next flight back.
15:58I go, let's go.
16:01Oh my gosh.
16:03I love it.
16:04This is what I do, though.
16:05This is what I do.
16:05And then tomorrow, I'll be like, why is Harry hitting on me?
16:09And it's like, well, I did this.
16:10I know that Harry is an absolute player, and I know I did the young thing, okay?
16:17I dated a 24-year-old.
16:19Historically, the guys that I'm attracted to are not the types of guys I should be with long-term.
16:24Talon wasn't wrong.
16:25I mean, since my divorce, I've been thinking with my Chi-Chi.
16:29But I feel close to the guys who are performing to you.
16:30Like, they make it all about them.
16:32Like, he was really respectful of you.
16:34He's so sweet.
16:35But like, here's what I noticed.
16:36Johnny and Talon, off camera, leading up to this, have been so nice.
16:41And then what happens is, these guys get nervous, right?
16:44Which, by the way, I can totally appreciate.
16:45But their go-to is to put me down and come for me.
16:49That is so f***ed up.
16:51I'm just like, f*** you guys.
16:52You want to know what's so weird?
16:54I had to go downstairs when you were doing the Laguna Beach thing because Talon made one comment where, like, my jaw dropped.
16:59And I'm like, this is Kristen's show in front of everyone, where he said, like, something about your list is getting too long.
17:04It's like, these guys love to just put me down in front of everybody.
17:09Also, Johnny, I'm trying to be like, you are so sweet.
17:11And then he told me I ran through everyone at Barrington.
17:13And I'm like, I didn't hook up with one f***ing person at Barrington.
17:18Not one.
17:19I don't even know who the f*** Tommy is.
17:21The only thing I can think about is later when I came back to visit a Tommy.
17:26But I did not hook up with anybody in Barrington.
17:29That's why I was like, say a name.
17:30I have nothing to f***ing hide.
17:33Do you want to trash me in front of my f***ing audience?
17:36It's like, so f***ed up.
17:38It's really f***ed up.
17:47It's like, so f***ed up.
17:49It's really f***ed up.
17:50Like, I hate Johnny.
17:52Why do I want to fight right now?
17:53I'm like, Talon, f*** you.
17:56It just gets to a point where it's like, I'm so sick of men, like, trying to f***ing beat me down.
18:00Like, it just gets really f***ing old.
18:04For me, it's so triggering because it's like every guy in my life, including my own f***ing dad, has done this s*** to me.
18:12I think because my dad is a narcissist, he always made me feel like I wasn't good enough.
18:17And for so many years, I was attracting similar types of men who were emotionally unavailable.
18:25In Chicago, it all just hit me like a ton of bricks.
18:28But it's just like, Jesus Christ.
18:31Everyone's so f***ing insecure.
18:34Yeah.
18:34All right, I'm over it.
18:35Let's go get an IV.
18:38Kristen, I love how you just got that out of your system.
18:40Now you're yourself.
18:41Yeah.
18:41How are you?
18:44I'm good, babe.
18:45This place is sick.
18:47Yeah.
18:47I'm so excited for an IV right now.
18:51Hi.
18:51I'm Rachel.
18:52Nice to meet you.
18:53I'll be starting your IVs today.
18:54Okay, awesome.
18:55Wait, last night during the show, Mark texted me, how's everything going?
19:00Really?
19:01And then he just texted me, I miss you.
19:04Oh.
19:05Oh, but you want something better?
19:06Yeah, I do, actually.
19:07Harry.
19:08Did I tell you about how he sent me a dick pic before?
19:09Yes.
19:10Look what he just texted me.
19:12I'm sorry.
19:14This was sent to you?
19:15The highs and lows, man, I can't remember.
19:16Babe.
19:17This is beautiful.
19:20Harry's f***ing high.
19:21Let me see.
19:24It's gigantic.
19:26But, like, imagine it rock hard.
19:28Ooh, you nasty.
19:29What?
19:30I would maybe make out with him in New York.
19:32Let me know how that goes.
19:33I will.
19:34Anywho.
19:35So.
19:35Can you catch me up?
19:36Okay, yeah.
19:37Johnny, this is what he texted me this morning.
19:38You were amazing last night.
19:40Thanks for such a fun escape from reality.
19:42Definitely needed that.
19:43You're going to absolutely crush the rest of the tour.
19:45No doubt about it.
19:47That's so wild.
19:49Yeah.
19:49That's slimy as f***.
19:51I'm not responding to that.
19:53I actually don't even care about, like, looking like an idiot in front of the audience.
19:55This is, like, a much bigger thing for me.
19:57It's the theme of my whole life.
19:59It was just talent.
20:00It's like, okay, it's expensive from talent.
20:02But then Johnny, it was like, oh, my God.
20:05Like, no guy's ever taken accountability in my life ever.
20:08But you know what's so great?
20:09Like, ten years ago, you would have, like, fed into it a little bit.
20:12Yeah.
20:12Like, you're so beyond those kind of people now that you see right through it.
20:15You're not going to do that s*** anymore.
20:16I've allowed these men into my life.
20:19And I can see it a mile away now.
20:21And that's just a nice reminder of how far I've come.
20:23Yeah.
20:24It's crazy because everyone thought that I was so confident growing up.
20:29But really, I was extremely insecure.
20:32I was actually in survival mode.
20:34Had I really loved myself, I wouldn't have put up with a lot of the s*** that I did.
20:38I'm going to be really serious about who I let in my life from now on.
20:41I can't wait to meet the amazing man who comes into your life.
20:45I'm never dating ever again.
20:46Okay, fine.
20:46Or that.
20:48Oh, wait.
20:49Hold on.
20:49Boston could be promising.
20:53Oh, my God.
20:54Look at this.
20:55Next time on Honestly Cavallari, the headline tour.
20:58The meal causes!
20:59You're such a badass.
21:01That's what you should be known for.
21:02Not for who you date.
21:04But let's talk about Rob.
21:05Oh, my God.
21:06He's such a big man that when he has to vomit, it's not the toilet, it's the bathtub.
21:12I'm waiting for my perfect.
21:13I think that that is such an easy find for you.
21:16No, it's not that easy, Justin.
21:18I'm saying that as a positive thing.
21:20I can't have a positive thing anymore.
21:22Check.
21:22I'm saying that.
21:29A perfect thing.
21:33I think that's a good thing.
21:34I think we're going to be doing power.
21:35I'm saying that.
21:36I don't even know.
21:37The Chains wow.
21:38I think that's a good thing.
21:39I'm saying that when I'm doing power.
21:40The Chainsaw45 is not that easy, it's not the thing.
21:43And I think that means it's powerful.
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