Inside Kendall Jenner's 'unusual' secret summit with Jacob Elordi... as family friends reveal her 'anxious' fear - and a 'sad and lonely' private heartbreak

As a Kardashian-Jenner it is no easy feat convincing people when you find love.

Congratulatory messages are often drowned out by accusations of a 'showmance' or a 'PR stunt,' with critics often adamant that these unions are the strategic moves of family mastermind and matriarch Kris Jenner.

And the pattern has been no different for Kendall Jenner, 30, who has been pictured on multiple secret getaways with her new boyfriend, Australian acting heartthrob Jacob Elordi, 29, since they first started dating earlier this year.

But critics may soon be humbled, for the Daily Mail has learned Kendall has taken a major step in their relationship.

After being implored to take Elordi out of the 'friend zone' by her younger sister, Kylie Jenner, Kendall has introduced the Wuthering Heights actor to her mom Kris, as well as her sisters Kim, Khloe and Kourtney Kardashian, and their A-list pals. It is not known if Elordi has met Kendall's half-brother Rob Kardashian.

Now, Kendall has made the rare and somewhat 'unusual' move of introducing Elordi to her father, Caitlyn Jenner.

The Daily Mail has contacted representatives for Kendall, Jacob and Caitlyn for comment.

The 76-year-old former Olympian has become estranged from the clan in recent years following comments she has made about the family, and her conservative politics, in particular voicing her support for President Donald Trump.

But an insider told the Daily Mail: 'Kendall finally introduced Jacob to Caitlyn in May.'

'This is a very big deal because Kendall does not introduce a lot of her friends or lovers to Caitlyn,' they continued. '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.'

We are told the extremely private meeting was held at Caitlyn's $3.5 million hilltop estate in Malibu.

'Kendall brought Jacob over to Caitlyn's house for a casual meet and greet,' said our insider. 'They hung out for a while one afternoon, it was not a big deal, it was super chill.'

The insider said there were no hiccups, adding: 'Kendall said it was "good," that everyone liked each other and it was nice, no talk about politics or Hollywood, just a nice chat.'

The highly anticipated meeting was planned as a relaxed event to calm down Jenner.

'Kendall has anxiety, so she wanted it to be super low key, she didn't want any drama at all,' our insider said.

They added that it was very important for Elordi to meet both of his girlfriend's parents as family is 'everything' to him.

'Jacob is very close to his mother Melissa and has said that family is everything so this was a must for him,' they said. 'Kendall loves that Jacob is so close to his mom, it's a green flag for sure.'

Kendall is close with Kris, but her relationship with her father has deteriorated somewhat in recent years, with the pair last seen in public together in 2022.

'I have to compartmentalize my relationship with my dad in a way because I love her,' she shared in a rare confessional on family's Hulu show The Kardashians last October. 'She's my dad. We have a good relationship. But sometimes I get frustrated with her with certain things because we just have completely different views on things.'

Kendall said that despite this, she always wants to 'include her' because she 'doesn't have a lot outside of her family and I think that she gets lonely,' adding: 'You don't ever want someone to be sad, especially your dad and someone you love and care about.'

Caitlyn married Kris in 1991, with the pair welcoming Kendall in 1995 and Kylie two years later. The marriage saw Caitlyn become a stepfather to Kim, Khloe, Kourtney and their brother Rob, supporting the children through the death of their biological father Robert Kardashian, who died in 2003.

Caitlyn and Kris split in 2014, with Caitlyn coming out as out as transgender the following year. She announced the news in a bombshell cover interview with Vanity Fair in which she also revealed she had changed her name from Bruce.

Soon followed I Am Cait, a reality TV show which aired for two seasons in 2015 and 2016, and her tell-all book, The Secrets of My Life, in 2017.

It was around this time that some relationships broke down. For despite supporting Caitlyn's transition, critical comments she made about Kris, including claims she was controlling and knew for years about her body dysmorphia, sparked a family rift.

Kim, 45, spoke out, branding Caitlyn a 'liar' for alleging in her memoir that their father Robert knew O.J. Simpson was guilty but defended him to get back at his ex-wife, Kris.

For her part, Caitlyn has been open about a familial relationship breakdown, telling British daytime show This Morning in October 2023 that she was cordial but no longer close with Kris.

In recent years, Caitlyn has made fewer red carpet appearances, with her last at the IAC National Summit at The Diplomat Beach Resort in Hollywood in January.

Kendall has, however, made an effort to spend time with Caitlyn since her father's best friend Sophia Hutchins died in a tragic ATV accident in Malibu on July 2, 2025.

The media personality and businesswoman, who also served as Caitlyn's manager, was 29.

'Kendall wants to be there for Caitlyn,' said our source. 'She has been sad and lonely since Sophia died a year ago.'