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Kristin Cavallari regrets this ‘wake-up call’ dating moment as a single mom

January 21, 2026
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Kristin Cavallari regrets this ‘wake-up call’ dating moment as a single mom

Kristin Cavallari was once caught discussing adult topics by friends of her school-age sons, and it made her re-think what she’s willing to discuss on her podcast.

“They told me recently that like a year ago or something when I was dating that younger guy, that their friends said they saw he and I played a drinking game or something on the podcast, and they saw some of the sexual stuff that we were talking about,” Cavallari said of sons Camden, 13, and Jaxon, 11.

The Uncommon James designer — who had been discussing her intimate life with ex Mark Estes — said during today’s episode of her “Let’s Be Honest” podcast that the incident “made [her] be like, ‘Whoa, I need to watch what I’m saying.”‘

She called it a “real eye-opener” and a “wake up call” as a single mom that “really made [her] pause.”

Kristin Cavallari smiling with her three children on a beach.
Kristin Cavallari revealed she had to take a step back on what she shares on her podcast after her sons’ friends revealed they heard her discussing adult topics. kristincavallari/Instagram
Kristin Cavallari takes a mirror selfie in a fitted yellow dress with a keyhole cutout.
The reality star called it an “eye-opener.” kristincavallari/Instagram

“I don’t care at the end of the day what Jax and Camden think about me. It’s my kids,” she told guest Rachel Bilson during the episode. “But I can’t be saying stuff that’s gonna affect them and their friends.”

The “Laguna Beach” alum, 39, said she’s since “found this way to kind of say stuff without just saying it.” 

The mom of three — who also shares daughter Saylor, 10, with ex-husband Jay Cutler, 42 — dated the much-younger Estes, now 26, for several months back in 2024.

Kristin Cavallari and Mark Estes smile at the camera.
Cavallari had been discussing her intimate life with ex Mark Estes. kristincavallari/Instagram
Kristin Cavallari kneeling between her two sons who are kissing her cheeks.
“I can’t be saying stuff that’s gonna affect [my kids] and their friends,” she explained during the podcast. kristincavallari/Instagram

A source told Us Weekly when they split in September 2024 that the former couple didn’t share the same long-term goals.

“As they started to get more serious in their relationship, issues started to surface,” the insider said at the time. “They kept having conversations about the future but weren’t aligned.”

While Estes wanted to “settle down and start a family” from “the start,” Cavallari was “very content with her life and family” after previously welcoming three children.

Kristin Cavallari and Mark Estes kissing at a restaurant.
Cavallari dated Estes back in 2024. kristincavallari/Instagram
Kristin Cavallari kissing Mark Estes on the cheek.
The former couple “weren’t aligned” in terms of their future goals. markestes/Instagram
Kristin Cavallari and Jay Cutler in Halloween costumes with their three children and a dog on their porch.
Cavallari shares her three children with ex Jay Cutler. kristincavallari/Instagram

“Having another baby was something Kristin wasn’t sure she was on the same page about,” the source divulged at the time, noting that their 13-year age gap was also a “big factor” in their decision to split.

“Them being in different stages of life was the dealbreaker,” the source noted.

As for her children, the reality star revealed last August that her two youngest are close to their mom —Jaxon and Saylor still spend the night in her room “one night a week.”

The post Kristin Cavallari regrets this ‘wake-up call’ dating moment as a single mom appeared first on Page Six.

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