Kristin Cavallari Reveals Craig Conover, Paige DeSorbo “Love Triangle”

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Kristin Cavallari is sharing the real timeline of her fling with Craig Conover.

As a die-hard admirer, I can’t hide my excitement anymore! The star of “Honestly Cavallari” has officially spilled the beans and admitted that she did share a romantic fling with the charming gentleman from “Southern Charm”. After all these years of whispered rumors, it’s a thrill to finally have this bit of juicy gossip confirmed!

Kristin clarified on “Watch What Happens Live” on June 4 that her friendship with Craig came first, but it turned romantic for a brief moment. As soon as she heard about Paige, however, she graciously and diplomatically extricated herself from the situation.

During a conversation led by host Andy Cohen, he inquired about potential overlap between Kristin’s affair with Craig and her previous three-year relationship with ex Paige. In response, the 38-year-old admitted that there had been some overlapping time periods.

Kristin recalled, “There was an image of Craig and Paige in New York that I’ll always remember, as if they were a couple. It was the first time we ever saw them like this, the first time I had even heard such news.

So, the Laguna Beach alum immediately distanced herself from the entanglement.

Kristin remembered saying to him after seeing the photo, “Hey, how about we stay as friends only?” She added, “I don’t want to get involved with whatever is going on.

She mentioned that she was caught up in a romantic predicament involving three people during high school, specifically her co-stars Stephen Colletti and Lauren Conrad on the show Laguna Beach. “I’ve learned my lesson and moved on. I have no intention of finding myself in such a complicated situation again.

In addition, the reality TV personality has announced that viewers will have an opportunity to witness her meeting up with Craig again in her upcoming show titled Cavallari’s Truth: On the Road with TopMob.

She shared with Andy that it was her first encounter with Craig since he started dating Austen (Kroll), and she also interviewed him about various topics, which will be featured in the podcast.

And Kristin definitely brought the heat.

“I asked him if he lied to me about Paige,” she added. “I went there. It will all be on the show.”

Since Craig has returned to the dating scene after splitting up with Paige in November, there’s a question about whether Kristin might consider rekindling their relationship at some point in the future.

“No,” the mother of three stated. “I love Craig as a friend.”

Apart from garnering attention due to her Craig disclosure, Kristin also admitted during the June 4 debut of “Honestly Cavallari” that she had a past romantic encounter with Glen Powell.

In my recent recollections, I found myself immersed in an unforgettable evening alongside my dear friend in Athens, Greece. And wouldn’t you know it, Glen was there too, adding to the already enjoyable atmosphere of our gathering.

But Kristin clarified, “I never f–ked him, I’m just putting that out there.”

In response to Justin’s statement, I admitted, “Indeed, we engaged in an imitative movement without actual intercourse.” Kristin chuckled and agreed, “Yes, that’s correct.

Keep reading for a look back at the rest of Kristin’s star-studded dating history.

Don’t forget to catch more astonishing disclosures by Kristin, airing every Wednesday at 10 p.m., only on TopMob.

The first love you experience is often hard to forget, especially when television cameras are capturing every up and down in a passionate relationship. Audience members got to witness the romance between Kristin Cavallari and Stephen Colletti unfold on the popular show “Laguna Beach” for two seasons. The couple, who started dating a year before filming began, along with Lauren Conrad, provided one of television’s memorable love triangles.

Kristin expressed in her 2016 book, Balancing in Heels, that she had deeply cherished and fiercely battled alongside Stephen, transforming their high school romance into the heart of a widely acclaimed television series. To Kristin, Stephen was the pinnacle of her existence, with nothing else mattering as much. She detested quarreling with him on screen because it felt like exposing all our private disputes.

Although their romantic relationship didn’t survive beyond high school, they’ve stayed close friends. In fact, Kristin has expressed interest in appearing on her show, Very Cavallari, according to TopMob News.

In an interview with TopMob News in 2022, Talan Torriero of Laguna Beach, known as a charmer, revealed that while the LC-Stephen-KCav triangle was capturing everyone’s attention, there were numerous other storylines unfolding backstage. He hinted that it wasn’t just about him, but also involved Kristin or even Lauren. Lauren, during her high school years, had relationships with other men who were quite impressive and chose not to be part of the show, or already appeared on it.

Regarding my tumultuous relationship with Kristin, I’d like to share that prior to the show’s debut, there were pre-existing connections, some might call them fleeting romances or encounters if you prefer. It wasn’t until my second season, or around that time, that I started getting closer to Lauren. As for Kristin, our relationship spanned from our junior to senior years, marked by on-again, off-again dynamics.

In the opening episode of the second season of “Laguna“, Stephen feels heartbroken upon discovering that Kristin has started dating a new man, Matt from USC, while he was away attending school.

It turns out that the individual at USC, whom we were referring to earlier, turned out to be none other than Matt Leinart, their renowned quarterback who later played in the NFL. Unfortunately, Matt didn’t make an appearance on MTV’s hit show and his relationship with Kristin didn’t last long.

In 2008, there were whispers about a possible reconciliation between Kristin and Matt after they were seen together in Las Vegas, but as it turned out, they didn’t formally reconnect.

In the course of time, before their staged relationship for later seasons of “The Hills,” Kristin and Brody Jenner had a real romance. This happened not long after Kristin’s time on “Laguna Beach” concluded, as they were introduced by Talan.

She revealed on Bethenny in 2012 that she dated Brody when she was 18, shortly after Laguna Beach, and as it turned out, their relationship was portrayed on The Hills for several episodes.

After being together for nearly a year, intermittently, they finally parted ways officially in 2006. When asked by People magazine, she explained that it was difficult due to her heavy workload. Despite this, they remain good friends.

In the beginning of 2006, Kristin and Nick Lachey, who is a member of the band 98 Degrees, stirred up rumors of a romantic relationship. This came about a year after his well-known separation from Jessica Simpson, his former spouse.

At that point in time, Kristin dismissed the speculations, stating openly to People magazine, “There’s simply no news here, no events happening. He’s a pleasant individual, but I must emphasize that we are only friends.

Initially, she claimed she was just avoiding the sudden, harsh spotlight that had fallen upon her. However, later on, she confessed it was merely an attempt to evade the intense, sudden focus of attention.

She stated during an episode of her podcast, “Let’s Be Honest,” in November 2024 that it was a period of great excitement in her life since she suddenly found herself on the cover of all tabloids. At that time, numerous photographers were constantly tailing my actions, camped outside my home.

Reflecting on my journey post-“Newlyweds” chapter with Jessica, I can’t help but reminisce about the whirlwind experience that swept through 2006 like an unstoppable tidal wave. It was truly a rollercoaster ride filled with excitement and surprises!

Not long after her relationship with Brody ended, Kristin started seeing actor Nick Zano, a familiar face from the WB sitcom “What I Like About You.

The relationship was quite intense between them; Kristin, in fact, got a tattoo of his initials on her wrist.

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

During my days on The Hills, as Kristin seemingly played out romantic scenes with Brody and Justin Bobby Brescia for the cameras, I found myself quietly harboring a secret romance off-screen.

Back in 2010, I was quietly romancing MTV cameraman Miguel Medina, maintaining the secrecy so well that not even my fellow castmates Heidi Montag and Audrina Patridge were privy to our love story.

In one episode of Very Cavallari, she confided to her ex-colleagues that we were secretly together for several months. At the same time, I was portraying a relationship with Brody on the show, while Miguel was unknowingly documenting it all.

She later explained that their relationship became public during their final days at work, as the media had photographed them at the airport a week prior to finishing the show, which ultimately led to their being discovered.

Following her breakup with Miguel, Kristin attracted the attention of NFL player Jay Cutler, who was then a quarterback for the Chicago Bears. After just a year together, Cutler made a significant move by proposing in 2011. However, their relationship did not last long as Kristin called it off a few months later. In her book “Balancing In Heels,” she explained that “some adjustments were needed.

After meticulously mapping out their Xs and Os, the duo welcomed their son Camden into their family in August 2012, tied the knot in June 2013, and expanded their team with sons Jaxon (arrived in May 2014) and daughter Saylor (born in November 2015). Although they appeared to be a strong unit, Kristin has recently disclosed details about their team dynamics since announcing the dissolution of their marriage in April 2020.

In an episode of The School of Greatness podcast in 2022, she admitted that the most terrifying experience in her life was going through a divorce. However, she also shared that it turned out to be the most beneficial decision she’s ever made, serving as a catalyst for her personal growth and self-discovery, helping her understand who she is now.

After her divorce from Jay, Kristin pursued humor by associating with comedian Jeff Dye in Los Angeles. However, during a live Instagram session in January 2021, they expressed the three small words, “It was never that serious to begin with.” An insider informed TopMob News in March that their relationship had ended. The source stated, “She was just having fun.

In November 2024, the comedian shared that they didn’t engage in a serious relationship. However, he clarified openly that she led him to believe there might be a possibility between them. He described how she acted affectionately towards him, similar to treating a pet dog.

By August 2021, Kristin had discovered a fresh duet companion in country musician Chase Rice. An informant shared with TopMob News that their collaboration is currently informal and recent. “Kristin has attended one of his concerts and they’re enjoying themselves,” the insider added at the time.

It eventually became clear that the Nashville locals had been focusing on individual performances, as Kristin herself mentioned on Instagram, “At present, I’m single.

 

In late 2024, a specific part of Kristin’s romantic history was revealed – her brief romance with the well-known country singer Morgan Wallen.

On an episode of Bunnie XO’s Dumb Blonde podcast in December, Kristin remarked, “He was an excellent casual companion. He was skilled in the bedroom.

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

On our initial date, he truly embodied chivalry, as she explained. He asserted confidently, “I’ll pick you up and decide on the location,” showing remarkable efficiency. Later, securing a private room at the venue we visited, he leaned in for a kiss under the rain, which she disclosed, was incredibly endearing.

Though Kristin affectionately referred to TikTok sensation Mark Estes as her “best boyfriend”, she openly acknowledged the challenges she faced due to their significant 13-year age difference.

In October 2024, she revealed on her podcast that she parted ways with Mark as she felt their relationship wouldn’t work out in the long run. It wasn’t due to lost love or any negative incidents, and neither cheated nor were they unkind. There was no wrongdoing; it was simply a difficult decision because such breakups often are.

To put it in my own words as a devoted fan, I firmly believe that he must seize the opportunities life offers him over the long haul. He’s still quite young, and I can sense it myself. As I reflect on my life at 24, I realize how much has transpired for me since then. Those years are pivotal; they shape you fundamentally. It’s during this phase that one discovers who they truly are, and he deserves the chance to do just that.

In April 2025, Kristin clarified that when she hinted about dating a retired athlete months prior, she was indeed talking about the ex-NHL player, as discussed on her podcast.

She explained that he is an individual who’s put considerable effort into self-improvement, and there was a profound emotional bond between them. Regarding their relationship, she characterized it as one of the most profound connections she’s experienced.

Later on the same day, Nate spoke about their relationship during his podcast, Energy Line, mirroring Kristin’s glowing compliments.

He exclaimed that she was really great company, adding they enjoyed themselves thoroughly. However, circumstances simply didn’t allow their relationship to continue smoothly.

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

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2025-06-05 19:18