NEWSKristin Cavallari’s Dating Disaster: Reality Star Exposes TMI Detail About Her 'Very Famous' Ex’s Manhood
Kristin Cavallari revealed her ex whipped out his private parts on an early date to show her his 'insecurity.'
June 2 2026, Published 4:12 p.m. ET
Kristin Cavallari called out an ex for an awkward sexual encounter.
During a Tuesday, June 2, episode of her “Let’s Be Honest” podcast, the reality star, 39, revealed she was taken aback when a celebrity she dated had a “mole on his d---.”
Kristin Cavallari recounted a disastrous date from four years ago.
“Maybe four years ago, I went on two dates with a very famous man and that’s all I’m going to say because I don’t want anyone to pinpoint who this might be,” she recalled, noting their outings were some of the “best dates” she’d ever been on. “Our second date, we went to the Beverly Hills hotel and he got a suite and we swam all day and took showers separately, and we ate dinner on the patio and it was great.”
During their evening, the star asked Cavallari, “You know how when you first start dating someone you have those insecurities about your body and you just wanna get them over with?”
Kristin Cavallari's Date Reveals His Biggest 'Insecurity'
Kristin Cavallari went on two dates with a 'very famous' man.
“He’s like, ‘I have a mole on my d---,’ and I was like, ‘Oh, OK! How bad is it?’” Cavallari remembered.
Much to her surprise, the man offered to show it to her.
“So he pulls out his d--- — first time I’ve seen it — and I’m sitting there saying, ‘I don’t see anything,’” she recalled. “This is mean, but he’s kinda known for having a big d---, and it wasn’t that big. I think that’s really what the insecurity was about.”
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Kristin Cavallari's date showed her a mole on his 'd---.'
Cavallari insisted she did not “touch” or do “anything with that d--- that was in [her] face.”
“Later I was thinking about it and I was like, ‘Oh my God, that’s what he tells every f------ girl to get his d--- out,” she said. “I think we made out, but I was like, ‘I’m not having s-- with you.’ I’m not gonna sleep with a guy right away.”
The fashion designer noted the guy also had a “flat a--” and “horrible backne scars.” After he “pulled out his moley d---,” she had no interest in ever seeing or dating him again.
Inside Kristin Cavallari's Split From Jay Cutler
Kristin Cavallari was previously married to Jay Cutler.
Cavallari was previously married to Jay Cutler for nine years before they finalized their split in 2022. The exes share kids Camden, 13, Jaxson, 12, and Saylor, 10.
Kristin Cavallari shares three kids with Jay Cutler.
In October 2024, the blonde beauty explained the source of the split during an emotional episode of her podcast.
"My heart broke in my marriage. Even though I'm the one that walked away, it was not what I wanted. It was not what I had envisioned," she expressed. "And I really tried f------ everything I could. It's just heartbreaking when you want something so badly but you just can't get there. And I would say my heart was broken for years in my marriage — I mean it was."
