Imagine if your juiciest, most intimate girls’ nights out took place in front of a live audience — with a few million more of your closest friends watching across the world, too. That’s the setup for Kristin Cavallari’s new show, Honestly Cavallari: The Headline Tour (E!, Wednesdays, 10 p.m.) — and some of the nuggets she lets slip are so private, we can’t believe we’re really allowed to hear them. From X-rated revelations about her love life to gossip about some of her reality TV frenemies, she’s not so much spilling the tea as throwing it at us.
Really, though, Cavallari’s decision to take her hit podcast “Let’s Be Honest” on the road for four dates in March made total sense: Knowing people would gossip anyway, why not take control of the situation? “This is the one time in my life I want to give ’em something to write about! Let’s give ’em some damn headlines!” she announced from the stage her first night.
She may have been just 17 when she started out on MTV ’s Laguna Beach: The Real Orange County, but these days, at 38 and with The Hills, Dancing With the Stars and her own reality show Very Cavallari behind her, she’s a total pro.
There’s a lot to talk about when it comes to Cavallari’s colorful life. She’s always been sassy, sexy and fun, but now those qualities come with a calmer confidence and maturity. She’s three years out of her marriage to Chicago Bears QB Jay Cutler, with whom she shares sons Camden, 12, and Jaxon, 10, and daughter Saylor, 9, and Honestly Cavallari shows that in many ways she lives the life of a normal mom. Based in Nashville, she juggles career (her Uncommon James lifestyle brand also has four retail locations) with school pickups and making dinner.
Dennis LeupoldAs for romance, she dated influencer Mark Estes after her divorce, but since their September 2024 split, she’s been single. And ready to mingle? She’s not so sure. While Cavallari dabbled with Raya — the exclusive dating app used by many a star — and is ultimately on a mission to find a good man, she knows more soul-searching is required to avoid repeating past mistakes.
We wanted to get the inside track, but just watching Honestly Cavallari wasn’t enough. She speaks to Us exclusively.
What made you decide to do another reality show?
I know I’ve said a million times I would never go back, and I stand by that because this is not a show about just my day-to-day life. I was already going on a podcast tour, so I thought, why not let cameras come along? I filmed the entire show in two weeks, and truly, it’s a docuseries in the best sense of the word, in that they just followed us. They let us do our thing. This is the most fun I’ve ever had on a show.
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This time, your kids are on camera, too. How did you come to that decision?
I wanted to wait until they were a little bit older to make a rational decision about having their lives exposed. They’ve been asking me for years to post them, show them, share them, and I’ve started a little. I think they may be in three or four scenes in the whole show — it’s not like I plastered them all over the place. Reality TV has been such a large part of my life for over 20 years, so being able to have this experience with my kids was actually nice and really enjoyable. You can see with Camden, he’s so excited to have a microphone on.
You say on the show that your divorce made you figure out your s***. What have you learned?
The last five years have been instrumental for me. I’ve had the most growth that I’ve ever had. I went through a lot of things in the last five years. Obviously, getting a divorce was the start of that, and cutting my dad out of my life. Growing up and realizing that what I had done previously wasn’t working for me and that I had to figure out what needed to change in order to set up the second half of my life to be peaceful. My whole life was never peaceful; even in childhood, it was always chaotic. I really value peace and stillness and quiet now, and I’ve worked really hard to get there. I’m happy I went through the hard times because I came out the other side stronger and way more in tune with who I am and way more comfortable in my skin.
Has the fact that you’re not dating contributed to that?
I think a lot of times dating was like passing time. Even though deep down I knew this is not my future husband, what I’ve realized is it’s all noise. I don’t need it, the distraction. It’s been really nice for me to have literally zero distractions on any front and just to sit with myself.
Kristin Cavallari Eric Ryan AndersonWhy did you want people to know you funded Uncommon James yourself and didn’t get a penny in your divorce?
I would say that’s one of the bigger misconceptions I see about me. I’m proud of what I’ve accomplished on my own.
How do you feel about WAG life now?
My experience was actually amazing. I didn’t go through any of the stereotypical drama you hear about. I loved the other women, and everyone was kind to me when I came in. That was a fun time, especially after I had kids and started taking them to the games. I will forever look at that time with fond memories.
Now, let’s talk about some guys on your show. On the June 11 episode, you and Harry Jowsey shared some moments on-stage and off …
What I love about Harry is he’s so authentic. I value authenticity. Harry is 1,000 percent himself. I also think Harry has such a big heart. I know he has sort of this player mentality, which is probably true, but I don’t experience that part of him. I just see this sweet, kind guy. I see some of my younger self in him, and we bonded instantly. I look at him like a little brother — but with the dick pic, everyone’s going to be like, what the hell? I’m not sexually attracted to Harry.
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But there were some flirtatious moments where you might’ve thought about crossing the line?
I’m a massive flirt. We’ve known this for over 20 years, but I flirt a lot with zero intentions of actually doing something. Sometimes I say a lot and don’t mean what comes out of my mouth.
Who was the most challenging guest you had on the tour?
Johnny, my very first boyfriend, which I thought was going to go very differently. To have him diminish what we had and almost make it purely about sex was really difficult for me. The tour ended up being way more personal than I had anticipated. Way more from my past came up, and it was a great opportunity for me to realize how far I’ve come, so I’m thankful for it, but that was the hardest night for me. I’m just not in a place in my life where I need to be gaslit, and I don’t need people in my life who can’t take any accountability.
Your old Laguna Beach costar Talan Torriero was on that episode too, and you were not pleased when he referenced your ex Mark Estes by saying, “I’m slowly turning into a Montana Boy.” Have you made up?
I love Talan, and we are good. I don’t think Talan on his own would’ve been that bad. It was the combination of the two on that night that really rocked me.
You also revealed that Lindsay Lohan once walked in on you and Talan in bed. Have you spoken to her since?
That sounds like she walked in on us being intimate, which wasn’t the case at all, I just want to clarify that. We were simply sleeping next to each other. I haven’t seen her in years, but we saw each other a few times after that incident and never had an issue.
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On the show, a fan asks about Lo Bosworth and Lauren Conrad from your days on Laguna and The Hills, to which your answer was “I hate Lo more…” Would you ever invite her on to talk things out?
I think everyone is trying to make this a much bigger deal than it is. I don’t hate Lo, I don’t even really think about Lo. I was joking around, but sarcasm never translates. I’m not sure the last time we talked; I would imagine it was during The Hills. I have zero beef with Lo, but we’re also not necessarily friends, which isn’t a negative. If I saw her, I would give her a big hug.
You’ve had some well-known friendship fallouts over the years. How do you view female friendships now?
I think some people come into your life for a season, and there are lessons to be learned. Overall, I’ve had the best girlfriends in my adult life. Most have been in my life for around 20 years. And I’ve made a few more recent friends through my kids. I don’t know what I would do without them.
Kristin Cavallari Dennis LeupoldYou also talked on the show about getting your breasts redone this past spring. Anything else planned?
I’ve mentioned that I would, maybe, do a facelift in 10 or 15 years or so. To me, that makes more sense than going the Botox and filler route, but we’ll see. The recovery scares me. Also, my mom hasn’t done anything and looks great, so if I can age like her, then I’ll be happy. I don’t plan on being in the public eye in 15 years, so hopefully I don’t feel the pressure to age a certain way.
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