Kristin Cavallari Details Craig Conover Hookup

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Kristin Cavallari is finally spilling the tea about her past with Craig Conover.

The former Hills star openly admitted to having a short-lived relationship with the Southern Charm actor, contrary to rumors involving his co-star Austen Kroll.

During the June 25th episode of Kristin’s TopMob series, Honestly Cavallari: The Headline Tour, Kristin asked me point-blank, “Was there anything between us?” To which I responded, “As for you and me, to be honest, no, nothing transpired between Kristin and myself.

In 2020, Kristin found herself at the center of speculations about romantic involvements with two popular figures from the Bravo world. However, later on, she set the record straight regarding their relationship, stating, “Craig and I started spending time together, while Austen was shouldering the blame for it.

During the live broadcast of her podcast, “Let’s Be Honest,” in New York, Craig reiterated, “At that time, nobody truly understood the situation. We all happened to meet each other and instantly got along, which was a lot of fun for everyone involved.

In a confessional, Kristin confessed, “I think we all know that it was more than kissing, okay.”

Later on, during a memory sequence, Kristin’s closest friend, Justin Anderson, learned about the reality stars’ romantic entanglements.

After the hairdresser inquired from the mother of three, “Were all your children born through the same route (vaginal delivery)? But that area is okay for you?” she humorously responded with, “Inquire with Craig instead.

She subsequently commented, “Approximately how often did I date Craig? I believe it was only one or two instances. It wasn’t a frequent occurrence.

After returning to the spotlight, Craig reminisced about his past with Kristin: “It was enjoyable, and looking back, I have no regrets. It was a great time, and then Paige DeSorbo and I began dating afterwards.

However, despite the assertion by the founder of Sewing Down South that a love triangle involving him, Kristin, and Paige did not exist (as they broke up in November after three years), Kristin remained uncertain about this claim.

During our intense talk, she questioned Craig about Paige: ‘Weren’t you being truthful with me when you said there was nothing between you two?’

Nevertheless, Craig maintained that the extent of overlap between the situations might not be as significant as some believe. Meanwhile, Kristin made it clear that they were not in a romantic relationship.

But Craig did later confirm, “Kristin is a great kisser, by the way.”

Following their interview, Craig was not so happy with the truth bombs Kristin revealed.

He confided in Austen backstage, “That was hands down one of the most foolish actions I’ve taken in my life. The entire situation revolved around Paige – it was insane! I can’t believe I did something so reckless.

As Austen then reminded his BFF, “Let’s de-mic. Before you start…”

1. Don’t miss out on completing the entire season of “Honestly Cavallari: The Headline Tour” on Peacock. Meanwhile, continue scrolling to revisit Kristin’s high-profile romantic past.

2. Catch up with all episodes of “Honestly Cavallari: The Headline Tour” on Peacock right away. In the interim, keep reading to reminisce about Kristin’s illustrious dating career.

3. Make sure you watch every episode of “Honestly Cavallari: The Headline Tour” available on Peacock. Simultaneously, take a trip down memory lane and re-explore Kristin’s celebrated love life by reading further.

4. Complete your binge-watching journey with the full season of “Honestly Cavallari: The Headline Tour” on Peacock. Meanwhile, catch up on Kristin’s notable romantic escapades as you keep reading.

5. Ensure you watch the entire series of “Honestly Cavallari: The Headline Tour” on Peacock. At the same time, delve into Kristin’s glamorous dating history by continuing to read.

The initial affection you hold dear…particularly when MTV’s cameras are present to capture each peak and trough in an emotionally charged relationship, is something that remains vivid. For two seasons, viewers had the chance to witness the romance between Kristin Cavallari and Stephen Colletti unfold on Laguna Beach, as these individuals, who started dating a year prior to the series’ filming, along with Lauren Conrad, provided one of television’s most memorable love triangles.

In Kristin’s 2016 book, Balancing in Heels, she expressed that we gave our love and battles our all, transforming our high school romance into the basis for a highly acclaimed television series. Stephen held significant importance in my life, with no other matter holding more value to me. I found it distressing to argue with him on screen because it felt like exposing all of our personal struggles publicly.

As their high-school love didn’t survive beyond graduation, we’ve managed to maintain a strong friendship. In fact, I even expressed my readiness to guest star on her show, ‘Very Cavallari’, as shared with TopMob News.

In an interview with TopMob News in 2022, Laguna Beach’s charismatic heartthrob Talan Torriero confessed that the LC-Stephen-KCav love triangle was just a small part of the story. “In truth,” he explained, “there were numerous other plotlines unfolding off-camera. Not only with me, but also with Kristin or even Lauren. While she was in high school, Lauren had relationships with some very interesting guys who weren’t keen on appearing on the show or were already part of it.

In regards to his tumultuous relationship with Kristin, Talan stated that prior to the show’s debut, some relationships or casual encounters were already underway. He didn’t start hanging out with Lauren until later, during his second season or so. His relationship with Kristin spanned from our junior and senior years, on and off.

Oh boy, in the thrilling kick-off of season two of “Laguna,” it absolutely wrecked me to discover that while I was away at school, my beloved Kristin had found solace in the arms of Matt, this charming fellow at USC. Talk about a heartbreaker!

Turns out, the individual at USC was none other than Matt Leinart, their renowned quarterback who later played in the NFL. However, he didn’t make it onto the cast of MTV’s hit show and his relationship with Kristin didn’t last long.

In 2008, there were whispers about a possible reunion between them after they were seen together in Las Vegas, but Kristin and Matt never formally reconciled.

In the subsequent seasons of The Hills, Kristin and Brody Jenner appeared to be in a romance that was staged, but it’s worth noting that they had actually dated years earlier following Kristin’s time on Laguna Beach. This initial encounter between them was orchestrated by Talan.

She confessed on Bethenny in 2012 that she went out with Brody when she was 18, following the airing of Laguna Beach. However, their relationship was only portrayed as ongoing for several episodes on The Hills.

Despite having an on-again, off-again relationship that lasted nearly a year, they formally ended things in 2006. According to her interview with People, she mentioned, “Things are tough for me since I’m working so much. We may not be together romantically, but we remain good friends.

In the early part of 2006, Kristin and Nick Lachey, who is a member of the band 98 Degrees, fueled dating rumors. This came about a year after his public breakup with Jessica Simpson, his then-spouse.

At that point, Kristin dismissed the speculations by stating to People magazine, “There’s simply nothing to discuss, no current events. He’s a great person, but I must clarify that we are just good friends.

Initially, she had been attempting to avoid the sudden, intense spotlight that was shining on her. Later, she confessed this.

Back in 2024, I found myself in an extraordinary phase of life. In a blink of an eye, I became the focus of all the gossip magazines, gracing their covers. During this period on my “Let’s Be Honest” podcast episode in November, I reminisced about that time. The days were filled with relentless paparazzi chasing my steps, always lurking outside my home, waiting for their next shot.

Following the conclusion of my “Newlyweds” chapter alongside Jessica, I can’t help but reflect on the incredible experience that marked 2006 for me. It was an exhilarating journey, indeed.

Following the end of her relationship with Brody, Kristin started seeing Nick Zano, a well-known actor recognized mainly for his role in the WB sitcom “What I Like About You.

The relationship was quite intense between them; Kristin went as far as getting his initials permanently inked on her wrist.

But when the pair called it quits in December 2007, Kristin had the tattoo removed.

During her stint on The Hills, Kristin was maintaining on-camera relationships with both Brody and Justin Bobby Brescia, but in reality, she had a hidden romance with someone backstage.

In the year 2010, Kristin was in a secret relationship with MTV cameraman Miguel Medina. Even her fellow cast members Heidi Montag and Audrina Patridge were unaware of this romantic connection.

In one episode of “Very Cavallari“, she shared that we had secretly been seeing each other for several months. During this time, I was also portraying a relationship with Brody on the show, while Miguel was filming our secret encounters.

I couldn’t help but exclaim, “Our secret relationship was ultimately unveiled near the conclusion of our professional journey, as the relentless paparazzi managed to snap our pictures at the airport a week prior to wrapping up the series. It was then that our clandestine bond was exposed to the world.

Not long after she broke up with Miguel, Kristin attracted the attention of Jay Cutler who was playing quarterback for the Chicago Bears at the time. In the first year of their relationship, Jay made a significant move by proposing in 2011. However, despite this gesture, Kristin called off the engagement a few months later, as she mentioned in her book “Balancing In Heels,” that there were certain aspects that required modification.

After carefully setting up Xs and Os, the duo became parents to son Camden in August 2012, tied the knot in June 2013, and later expanded their family with son Jaxon in May 2014 and daughter Saylor in November 2015. Despite appearing as a strong team, Kristin has shared insights about their relationship dynamics since they announced their divorce in April 2020.

On The School of Greatness podcast in 2022, she shared that the most terrifying experience for her was going through a divorce. However, she also stated that it turned out to be the most beneficial thing she’s ever done, serving as a catalyst for her personal growth and self-discovery, particularly regarding understanding who she is now.

After her divorce from Jay, Kristin explored humor with Los Angeles comedian Jeff Dye. However, although they said those three significant words during a live Instagram session in January 2021 (“It was never that serious to begin with”), an insider informed TopMob News in March that their relationship had ended. The source explained that Kristin was simply enjoying herself.

In November 2024, the comedian shared an account of their interaction. He clarified publicly that they didn’t have a serious romantic relationship. However, he admitted that she led him to believe there was a possibility between them. She behaved towards him as if he were a pet dog.

By August 2021, Kristin had discovered a fresh duet partner in country singer Chase Rice. An informant shared with TopMob News that things were still casual as it was a new collaboration. “She has attended one of his concerts already, and they are enjoying themselves,” the source added.

However, after several weeks had passed, it seemed that the Nashville locals were primarily enjoying performances by themselves. Kristin made this clear on Instagram, stating, “At present, I’m not involved in any romantic relationship.

 

In late 2024, Kristin finally revealed a significant aspect of her past relationships – her brief romance with the well-known country singer, Morgan Wallen.

In a December episode of Bunnie XO’s Dumb Blonde podcast, Kristin expressed that he was an excellent casual partner. She indicated that he was skilled in intimate encounters.

And he’s got some smooth moves out of the bedroom as well. 

On our initial date, he truly embodied chivalry, she noted. He said casually, “I’ll pick you up and decide where we go,” taking care of everything effortlessly. Later, after visiting a venue, he secured us a private room. She shared, “He kissed me in the pouring rain,” she confessed, and it was the most tender moment.

Despite Kristin calling Mark Estes the “best boyfriend” she’s ever had as Montana Boyz TikTok star, she openly admitted that the 13-year age difference between them was a challenge for her.

She disclosed on her podcast in October 2024, shortly after ending her seven-month relationship with Mark, that their long-term compatibility wasn’t right. She clarified that it wasn’t due to a lack of love or any negative incidents, such as infidelity or rudeness. No one had done anything wrong in this case. Those breakups, she believes, are often the most challenging.

Essentially, she said, “In the end, I believe it’s essential for him to live and grow because these are his formative years. He’s still young, and I can feel the weight of age a bit more now, looking back at my life at 24. So much has happened to me since then, and those years are crucial for personal development. This is when you discover who you really are, and he needs that opportunity.

In April 2025, Kristin clarified that when she playfully hinted about dating a retired sportsman earlier, she was actually talking about the ex-NHL player she mentioned on her podcast.

She stated that he is an individual who has put in significant effort into personal growth, and there was a profound connection between them. Regarding their romantic relationship, she described it as one of the more profound connections she’s experienced.

Later on the same day, Nate talked about their relationship on his own show, Energy Line, mirroring Kristin’s heartfelt compliments in his discussion.

He enthusiastically agreed, “She’s quite charming,” he said. “We shared some enjoyable moments. Sometimes, despite our best efforts, life simply doesn’t align.

Watch a brand new episode of Honestly Cavallari: The Headline Tour Wednesdays at 10 p.m. on TopMob.

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2025-06-26 05:47