Finding lasting love is never easy when you’re part of the Kardashian-Jenner family, where every new romance is immediately met with skepticism.
Kendall Jenner‘s relationship with the Australian actor Jacob Elordi has already resisted claims that it is just another carefully orchestrated publicity move.
However, behind the scenes, the model has quietly taken a major step that suggests their romance is becoming much more serious, a step that also sheds light on her complicated connection to Caitlyn Jenner.
Kendall Jenner makes a rare move with Jacob Elordi
Since Kendall Jenner and Jacob Elordi first tied the knot earlier this year, the couple has kept much of their romance out of the spotlight.
Although they were photographed enjoying a low-key vacation together, many critics dismissed the relationship as another Kardashian-Jenner “set-up” allegedly orchestrated by family matriarch Kris Jenner.
However, new developments suggest that Kendall is treating the relationship very differently.
After apparently being encouraged by her sister Kylie Jenner to get Elordi out of the “friend zone,” Kendall introduced the “Written Heights” star to the people closest to her.
Elordi has previously met Kris with her sisters Kim, Khloé and Kourtney Kardashian, as well as several famous family friends.
However, the most important step wasn’t introducing him to Kris. Instead, it led to him meeting Caitlyn, something that insiders describe as both highly unusual and deeply meaningful given Kendall’s longtime approach of keeping that part of her life separate.
Kendall arranges a private meeting with Caitlyn
According to a Daily Mail insider Kendall Jenner quietly introduced Jacob Elordi to Caitlyn a few months ago during a private viewing at the 76-year-old’s $3.5 million hilltop Malibu home.
“Kendall finally introduced Jacob to Caitlyn in May,” the source revealed. The source emphasized how important the meeting was, explaining, “It’s a really big deal because Kendall doesn’t introduce many of her friends or lovers to Caitlyn.”
While Kris is known for immediately welcoming people into her children’s lives, Caitlyn’s situation is very different.
“Everyone meets Kris right off the bat because she’s very social and involved with her kids, but not Caitlyn, who’s more of a recluse these days, so that’s very special and unusual,” the source continued.
Rather than showing up to a formal family gathering, Kendall intentionally kept it relaxed. “Kendall brought Jacob over to Caitlyn’s house for a casual hangout,” the source shared, adding, “They hung out for a while one afternoon, it was no big deal, it was super cool.”
According to the source, the visit went well as Kendall revealed that it was fun and everyone liked each other.
Kendall Jenner wanted to keep the introduction drama-free
The intimate encounter wasn’t just about introducing a boyfriend. This was carefully planned with Kendall’s comfort in mind.
According to the source, the reality star suffers from anxiety and wanted the meeting to be low-key and drama-free.
The meeting was also important for Jacob Elordi himself. Family has long been one of the actor’s main priorities, so it is important for him to get to know both of Kendall’s parents.
“Jacob is very close to his mother Melissa and said family is everything, so this was a must for him,” the source said.
They added that Kendall considers her boyfriend’s relationship with his mother one of his most attractive qualities.
Although Kendall and Caitlyn Jenner remain close in many ways, political differences and family tensions have complicated their relationship. Still, the 30-year-old made it clear she didn’t want her father to feel isolated.
In an October 2025 episode of “The Kardashians,” Kendall admitted that she always wanted to “include” the media personality because she didn’t have “much outside of her family and I think she feels alone.”
She also added, “You never want anyone to be sad, especially your dad and someone you love and care about.” Family history helps explain emotional complexity.
Caitlyn married Kris in 1991 before welcoming Kendall in 1995 and Kylie two years later. She also became stepfather to Kim, Khloé, Kourtney and Rob Kardashian after the death of their father, Robert Kardashian, in 2003.
After the former couple split in 2014 and Caitlyn publicly transitioned the following year, relationships within the family changed.
In 2023, however, Caitlyn acknowledged during an appearance on “This Morning” that she and Kris remained cordial but were no longer particularly close.
Kendall Jenner supports Caitlyn during a difficult chapter
Recent events have given Kendall another reason to reconnect with her father.
Caitlyn has largely stayed away from the Hollywood spotlight, making only occasional public appearances, including one at the IAC National Summit at the Diplomat Beach Resort earlier this year.
Behind the scenes, she also endured a heartbreaking personal loss. Sophia Hutchins, Caitlyn’s longtime manager, business partner and best friend, died in a tragic ATV accident in Malibu on July 2, 2025, at just 29 years old.
Since then, Kendall has reportedly made a conscious effort to spend more time with the media personality while navigating her own growing relationship with Elordi.
“Kendall wants to be there for Caitlyn,” a source shared, adding, “She’s been sad and lonely since Sophia died a year ago.”