Kristin Cavallari has some wild stories in her archive!
The on-air personality, as usual, opened up on her podcast, and this time, it was about her date with “a famous,” mystery man a few years ago, which left some vivid scenes in her memory.
Kristin Cavallari ended a 10-year marriage to her ex-husband and former NFL player Jay Cutler in 2020 and recently dated former hockey player Nate Thompson, although they eventually split.
The reality star recalled her unexpected dating experience, and while she kept the name of her date private, she did not hold back on her feelings during and after the encounter. On the recent episode of her “Let’s Be Honest” podcast, she noted that the date happened roughly four years ago, and the two dates started on a very encouraging note.
Admitting that they were one of the best dates she has ever been on with “a very famous man, first at the Sunset Tower Hotel, then at the Beverly Hills Hotel.” The two acquaintances at the time got a suite, swam all day, showered separately, and settled for a nice dinner on the patio for their second date.
Everything seemed to be going well until the conversation took an unexpected turn and the man began discussing the physical insecurities people often feel when getting to know someone new. The guy, in the spirit to quickly get over that phase, informed her about the mole on his private part, asking if she would like to see it.
Cavallari revealed that the moment caught her off guard and completely shifted the atmosphere of the date. In hindsight, the reality star questioned whether the interaction may have been something the man routinely did as a way to create intimacy early on.
The Reality Star Was Glad She Ended Things Very Early
Cavallari continued that she discovered why he was insecure about his private part because it was a direct contrast to the reputation he has held over the years about the size of his manhood. However, the reality star uncovered another layer of turn-offs as soon as her date got out of his swimsuit.
The former E! television personality recalled the famous personality having “the flattest ass and horrible bacne scars,” making her realize his insecurities were probably much more than she thought. Cavallari declared that things changed after that second date, and she never saw the mystery man again.
She was especially grateful not to have gone overboard with him when it came to the physical intimacy aspect of their meeting. The reality star continued that her date later unraveled to be a full-blown narcissist who wanted to control, making her even happier that she dodged a bullet.
Cavallari insisted that her personality has never been listed as part of anyone on her dating history list, and she would keep it that way.
Inside Kristin Cavallari’s Expansive Dating History
The author’s major public relationship was with Stephen Colletti while they were in high school on “Laguna Beach.” The relationship and the love triangle with castmate Lauren Conrad were one of the show’s signature storylines and brought Cavallari before a national audience.
As stated by PEOPLE, Cavallari went on to become involved with a number of public figures, such as Matt Leinart and Brody Jenner, after “Laguna Beach.” Her most notable relationship was with Cutler, whom she began dating in 2010 and married in 2013 after a split.
The duo welcomed three children, and after their divorce, Cavallari admitted that it was a difficult decision, but it had to happen because it had been weighing her down for years. After her divorce, she was rumored to be in a romance with comedian Jeff Dye, who also appeared with her in public and posted affectionate remarks on Instagram.
Recently, Cavallari was also rumored to be dating popular social media personality Mark Estes. Their relationship was discussed due to their age difference, but Cavallari later stated that the breakup was not about controversy; it was about timing, priorities, and being at different stages of life.
She also went on to confirm a brief romance with former NHL player Thompson, saying it was one of the deeper relationships in her life. Cavallari admitted that their connection was based on intellectual compatibility and emotional chemistry; however, she decided not to make it more serious because she wanted to invest in herself and her career.
Cavallari Picked Out A Few Relationship Red Flags
Back in March, The Blast reported that Cavallari shared her thoughts on social media behavior in relationships, noting that a male partner hitting the like button on random women’s posts may be a cause for alarm. She believes that regular interaction, particularly by liking someone’s posts regularly, can at times be more deliberate.
Cavallari advised women not to be too controlling of who their partners follow online, since that should not be enough to raise red flags. Meanwhile, she also noted that there is a difference between being followed and going out of one’s way to sustain attention by communicating with followers repeatedly.
Drawing from her own experiences, Cavallari revealed that she has received attention from men on social media who she claimed were already in committed relationships. She singled out married men who have regular contact with stories or posts and maintain a public image of a family life online.
The TV personality remembered one example where a married man had his wife on his profile, but went on to repeatedly interact with her posts. Cavallari acknowledged that the actions were frustrating and that sometimes she would like to see partners be more conscious of those interactions.
She subsequently attacked what she calls performative loyalty online, stating that some people act one way in public and another way in private. While Cavallari said that, admittedly, everyone has their own personal limits with their relationships, she made note that sometimes, the repeated online engagement might say more than somebody intends.
Kristin Cavallari Reflected On Her Early TV Days
While Cavallari was basking in the glow of the ninth anniversary of her jewelry brand Uncommon James, she also brought back a bit of the past with a revisit to her days on “Laguna Beach” days later.
The group discussed their pay for Season 1 on the game of “First We Feast” on TikTok with former Season 1 cast members Conrad and Colletti. Cavallari surprised her castmates after recalling earning a slightly higher amount per episode, prompting reactions from both Conrad and Colletti.
Cavallari revealed that she always thought everyone was paid the same and joked that she would have filmed the show for free anyway. However, the producers subsequently increased their pay to become equal, although it was not significantly higher.
It arrived as a result of renewed interest in “Laguna Beach” after the reunion special, and served as a reminder of how far the now-famous rivals Cavallari and Conrad have come, as they are now best of friends.
What wild story will come from Kristin Cavallari next?