Finding lasting love is never simple when you’re part of the Kardashian-Jenner family, where every new romance is immediately met with skepticism. 

Kendall Jenner’s relationship with Australian actor Jacob Elordi has already weathered claims that it’s nothing more than another carefully orchestrated publicity move. 

However, behind the scenes, the supermodel has quietly taken a significant step that suggests their romance is becoming far more serious, one that also shines a light on her complicated bond with Caitlyn Jenner.

Kendall Jenner Makes A Rare Move With Jacob Elordi

Ever since Kendall Jenner and Jacob Elordi were first linked earlier this year, the couple has kept much of their romance away from the spotlight. 

While they’ve been photographed enjoying discreet vacations together, many critics dismissed the relationship as another Kardashian-Jenner “showmance” allegedly masterminded by family matriarch Kris Jenner.

However, new developments suggest Kendall is treating the relationship very differently.

After reportedly being encouraged by sister Kylie Jenner to move Elordi out of the “friend zone,” Kendall introduced the “Wuthering Heights” star to the people closest to her. 

Elordi has already met Kris along with sisters Kim, Khloé, and Kourtney Kardashian, as well as several of the family’s celebrity friends. 

However, the biggest milestone wasn’t introducing him to Kris. Instead, it was bringing him to meet Caitlyn, something insiders describe as both highly unusual and deeply meaningful given Kendall’s long-standing approach to 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 in a few months ago during a private visit to the 76-year-old’s $3.5 million Malibu hilltop home.

“Kendall finally introduced Jacob to Caitlyn in May,” the source revealed. The insider emphasized just how significant the meeting was, explaining, “This is a very big deal because Kendall does not introduce a lot of her friends or lovers to Caitlyn.”

While Kris is known for immediately welcoming the people in her children’s lives, Caitlyn’s situation is very different.

“Everyone meets Kris right off the bat because she is so social and involved with her kids, but not Caitlyn, who is more of a recluse these days, so this is very special and unusual,” the source continued.

Rather than making the introduction into a formal family gathering, Kendall kept everything intentionally relaxed. “Kendall brought Jacob over to Caitlyn’s house for a casual meet and greet,” the insider shared, adding, “They hung out for a while one afternoon, it was not a big deal, it was super chill.”

According to the source, the visit went smoothly as Kendall revealed that it was nice and everyone liked each other.

Kendall Jenner Wanted The Introduction To Stay Drama-Free

The intimate meeting wasn’t simply about introducing a boyfriend. It was carefully planned with Kendall’s own comfort in mind.

According to the source, the reality TV star struggles with anxiety and wanted the meeting to be low-key and void of drama. 

The meeting also mattered to Jacob Elordi himself. Family has long been one of the actor’s top priorities, making it important for him to get to know both of Kendall’s parents.

“Jacob is very close to his mother Melissa and has said that family is everything so this was a must for him,” the insider said. 

They added that Kendall sees her boyfriend’s relationship with his mother as one of his most attractive qualities.

Kendall Has Never Hidden The Challenges In Her Relationship With Caitlyn

Although Kendall and Caitlyn Jenner remain close in many ways, political differences and family tensions have complicated their relationship. Still, the 30-year-old has made it clear she doesn’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 a lot outside of her family and I think that she gets lonely.”

She also added, “You don’t ever want someone to be sad, especially your dad and someone you love and care about.” The family’s history helps explain the 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 following the death of their father, Robert Kardashian, in 2003.

Following the former couple’s 2014 split and Caitlyn’s public transition the following year, relationships within the family shifted. 

In 2023, Caitlyn, however, acknowledged during an appearance on “This Morning” that she and Kris remained cordial but were no longer particularly close.

Kendall Jenner Is Supporting Caitlyn During A Difficult Chapter

Recent events have given Kendall another reason to reconnect with her father.

Caitlyn has largely stepped 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’s 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 has been sad and lonely since Sophia died a year ago.”