Kristin Cavallari Says Women Should Ditch the Rules and Date Younger Men

Kristin Cavallari is not sweating the whole younger-guy-older-woman thing. In fact, she is very here for it — and, to be fair, she has lived it.

Where she stands on age gaps right now

On Saturday, April 11, the 39-year-old posted a burst of thoughts on her Instagram Stories after someone asked about younger men dating older women. Her take: older women tend to be more comfortable in their own skin, there is less game-playing, and they are a lot clearer about what they want. Also, the slight sense that it is 'breaking rules' just makes it more fun.

'I love this era for us!'

The Mark Estes chapter (and why it ended)

Cavallari dated TikTok creator Mark Estes for seven months in 2024. There was a 13-year gap between them, which she later admitted was part of why they called it. On her Let’s Be Honest podcast in October 2024, she explained that she ended it because, long-term, it was not the right fit. No cheating, no drama — which, yes, actually makes those breakups harder. She even called Estes the best boyfriend she has ever had, but felt he still needed time and space to go live more life.

Where her head is now

Since her 2013–2020 marriage to retired NFL quarterback Jay Cutler — they share three kids — Cavallari has been open about easing back into dating at her own pace. Earlier this month, she told Us Weekly she is not actively looking and, even if Mr. Right walked in today, she is not sure how that would fit into her schedule. Between work (Uncommon James is still her thing) and the kids, she says life is full. On the practical side, she gets every other weekend to herself when the kids are at their dad’s, and she loves that recharge time enough that she is not ready to give it up.

Reunion vibes and a friend’s read

She also just got the Laguna Beach gang back together for a reunion special on Roku — a very 2020s sentence that somehow fits her world perfectly. Her former castmate Talan Torriero, also 39, told Us this month that Cavallari keeps her standards high and her list long, and he is all for it. In his words, she is a total catch — successful, close with her kids, and dialed in — and he thinks the right guy is basically around the corner.

Quick timeline

• April 11: Cavallari, 39, backs age-gap dating on Instagram Stories, saying older women bring confidence and clarity — and rule-breaking fun.
• 2024: Dates TikTok star Mark Estes for seven months despite a 13-year age difference.
• October 2024: On her Let’s Be Honest podcast, says she ended things with Estes for long-term compatibility reasons; calls him the best boyfriend she has had and notes he needs time to experience life.
• Post-divorce (2013–2020 marriage to retired NFL QB Jay Cutler; three kids): Tells Us Weekly earlier this month that dating is not a priority and she values her solo weekends to recharge.
• Recently: Reunites with her high school crew on Roku’s Laguna Beach special; Talan Torriero says she is a catch and predicts the right guy is close.

Bottom line: Cavallari likes the age-gap conversation because it speaks to confidence, not controversy. And while her last relationship was good on paper (and sweet in practice), she is choosing the long game — and her quiet weekends — for now.