Scott Disick Reveals Surprising Shift in His Relationship With Caitlyn Jenner: ‘I’ve Never Gotten Along That Good With Her’

Scott Disick admitted he experienced a breakthrough moment with Caitlyn Jenner, revealing that a recent gathering marked the best dynamic the two have ever shared. Reflecting on a visit to Kendall Jenner’s new house, Disick noted a stark, positive turnaround in their historical relationship.

The candid revelation unfolded during an episode of Hulu’s The Kardashians. Disick and Caitlyn had joined forces to help Kendall prepare her property for her horses, leading to unexpected camaraderie.

“I loved it there that day,” Disick told Kendall while looking back on the property visit. “And I felt like your dad, too, was in such a good mood. I’ve never gotten along that good with her in, like, ever.”

An Unlikely Alliance at Kendall Jenner’s New Property

Kendall validated the surprising shift between the two long-standing family figures, pointing out how smoothly they interacted on site. “You guys chopped it up,” Kendall noted during their debrief.

While the visit included an awkward moment sparked by a NSFW comment from Caitlyn, Disick emphasized that the mood stayed genuinely lighthearted throughout the day.

“I don’t know, she was just fun to chill with. She was funny.”

Scott Disick, Caitlyn Jenner and Kendall Jenner hangout

The easy banter caught viewers’ attention because Disick, 43, and Caitlyn, 76, rarely shared one-on-one comedic moments across their years in front of the cameras.

The Evolution of Caitlyn Jenner’s Presence on Hulu

Caitlyn was once a regular fixture on the family’s original E! series, Keeping Up with the Kardashians, which wrapped in 2021 after a 20-season run. In contrast, her appearances on the Hulu revival have been exceedingly rare.

The horse-prep hangout marked only Caitlyn’s second time filming for The Kardashians. Her first appearance occurred during season 7, when she surprised the family at a milestone event.

Breaking Down the Reality TV Appearances

Public perception often assumes Caitlyn is permanently estranged from all family filming, but documented appearances tell a more nuanced story of occasional, select reunions.

Her initial appearance on the Hulu platform happened when Kris Jenner extended a last-minute invitation to a farewell dinner at her former Hidden Hills residence.

Kris and Caitlyn were married from 1991 to 2014, sharing decades in the residence featured heavily across early reality seasons.

Caitlyn Jenner and Kendall Jenner on The Kardashians

Behind the Family Gatherings

Kendall admitted in a confessional that she never expected her father to attend the Hidden Hills farewell dinner. She described the connection between her parents as “distant,” though not inherently bad.

“My mom’s had a hard time inviting my dad to some of our family gatherings in the past, so it makes me happy that Kylie and I didn’t have to ask for my dad to be invited and that my mom just thought it was a good idea.”

Kris echoed that sentiment, noting the shared history warranted closing that chapter together as an entire group.

“It’s been a really long road, but it was Caitlyn’s house too,” Kris explained at the time. With Disick now praising their current dynamic, the blended family continues to carve out unexpected common ground.

💬 Seeing family dynamics evolve after years of distance is always fascinating.

✨ From awkward exchanges to genuine laughs, long-standing connections can still find common ground.

👇 Were you surprised to see Scott Disick and Caitlyn Jenner getting along so well? Drop your thoughts in the comments below!