Kristin Cavallari has once again captured the public’s attention, this time during a candid appearance on “Watch What Happens Live” last Wednesday night. The 38-year-old reality star and podcaster opened up about her tumultuous relationship with Craig Conover, the implications of his current relationship with Paige DeSorbo, and some eyebrow-raising moments from her past romances.

Kristin Cavallari discusses her past relationships and future plans on “Watch What Happens Live”.
During the episode, Kristin did not shy away from detailing her brief romance with Craig, which she described as a friendship that quickly spiraled into something romantic. “So Craig and I were friends first, became romantic for two seconds, the second I caught wind of Paige, I very politely excused myself from the situation,” she stated, explaining how a photo of Craig with Paige in New York prompted her to step back.
This revelation offers insight into the dynamics of love triangles, particularly as Kristin candidly remarked, “I was already in a love triangle in high school. I’m good for the rest of my life. I’m never gonna be in another one.” This statement resonates with many who have experienced the complexities of romantic entanglements.
Reflecting on her relationship history, Kristin also addressed rumors of a romance between her ex-husband Jay Cutler and Madison LeCroy. When asked if anything occurred between the two, she affirmed, “Yes. Yes. Yes,” affirming the whispers that had swirled around their liaison.
The conversation then moved to her time with actor Glen Powell. Kristin humorously referenced their previous encounter, stirring her followers’ curiosity by saying, “Did I say that? Funny how that happens… [But] pants were involved.” Such playful comments keep her audience engaged and eager for more insights.
As the episode unfolded, fans were treated to a nostalgic analysis of reality TV culture, especially regarding her interactions on “The Hills.” Kristin expressed interest in possibly filming another season of the beloved show, favoring it over “Laguna Beach.” She even reminisced about her experiences with co-star Brody Jenner, revealing, “Brody and I had a whole fake relationship… it’s way more fun when you pretend,” poking fun at the scripted nature of reality television.
In a world where reality TV often blurs the lines between fact and fiction, Kristin’s revelations demonstrate the complex nature of relationships formed under the scrutiny of cameras. Her willingness to discuss these personal experiences candidly allows her fans to relate and engage with her journey.