The Mole Scheme: Kristin Cavallari's Wildest Dating Story Yet

Kristin Cavallari has seen a lot in her decades in the spotlight, but even she was caught off guard by what unfolded on a luxe Beverly Hills hotel date four years ago. During the Tuesday, June 2 episode of her“Let’s Be Honest”podcast, The Hills alum opened up about two dates with a famous man—someone so recognizable she’s keeping his identity under wraps to avoid the inevitable guessing game.

On paper, the second date hit all the right notes. They booked a suite at the Beverly Hills hotel, spent the day swimming, showered separately, and capped it off with dinner on the patio. Sounds perfect, right? Here’s where it gets weird. Mid-date, her companion decided to share his body insecurity—he had a mole on his genitals. Innocent enough. But then he asked to show her. What followed was a masterclass in misdirection that Cavallari herself pieced together later: the real insecurity wasn’t about the mole. It was about the fact that despite his reputation for being generously endowed, well, he wasn’t. She found the whole ploy so transparent that she concluded this must be his go-to move with every woman he meets.

The kicker? Cavallari also noticed he had a flat backside and severe bacne scars—details that didn’t exactly seal the deal. She made it clear nothing physical happened beyond making out, and she certainly wasn’t going to sleep with someone on a second date anyway. After he“pulled out his moley d***,”as she so eloquently put it, she never saw him again.

Meanwhile, Cavallari’s own romantic history took a very different trajectory with Jay Cutler, whom she married in 2013 after meeting in 2010. The pair had three kids together—Camden, now 13; Jaxon, now 12; and Saylor, 10—before announcing their separation in April 2020 and finalizing their divorce in June 2022. These days, she’s flying solo and apparently collecting stories that are far more entertaining than anything that actually leads to a relationship.