Yes, Caitlyn and Kylie are very close, speaking almost daily and bonding over makeup and fashion, while Caitlyn and Kendall have a good but sometimes strained relationship due to different views, though Kendall still prioritizes including her dad. Caitlyn has expressed feeling particularly close to Kylie, who is more of an "open book," but still loves both daughters dearly, despite occasional frustrations with Kendall's more secretive nature and differing opinions.
Caitlyn said she and Kylie are “closer most of the time”
In a January 2021 interview on Dear Media's The Skinny Confidential Him & Her podcast, Caitlyn revealed that while she has more in common with her daughter, Kendall Jenner, she's felt closer to her youngest, Kylie Jenner.
Speaking on a recent episode of 'The Kardashians', the 29-year-old described the relationship as "distant," saying that while she loves her, she is often "frustrated with her with certain things." "I have to compartmentalize my relationship with my dad in a way," Kendall explained in a confessional.
Kendall Jenner has publicly shared her struggles with anxiety, including panic attacks, and sleep paralysis, a condition where she temporarily can't move or speak while falling asleep or waking up, which she linked to stress and lack of sleep. She's spoken about these experiences on her show and in interviews, discussing how they affect her, her perfectionism, and her need for coping mechanisms like breathing exercises and therapy, even mentioning a brain scan confirmed her anxiety.
Kylie Jenner has publicly shared her struggles with postpartum depression (PPD) after both of her pregnancies and, more recently (late 2025), revealed she's been dealing with chronic back pain for nearly three years, leading her to undergo stem cell therapy for relief. She also previously mentioned a diagnosis of recurrent corneal erosion syndrome affecting her eye.
There's no single "nicest" Kardashian as it's subjective, but Khloe Kardashian is often called the kindest and most relatable, known for her empathy and "Good American" brand empowering women, while some sources highlight Kim Kardashian's surprising warmth and Kris Jenner's excellent manners with staff, with many fans also finding Kylie Jenner sweet and Kendall chill, but opinions vary widely.
Caitlyn Jenner has said “Bruce” raised her children and she can enjoy time with them as she reveals her grandchildren call her "Boom Boom". She said she would always be their father “till the day I die”.
Kylie Jenner is significantly richer than Kendall Jenner, with recent estimates placing Kylie's net worth around $670-$700 million, primarily from her Kylie Cosmetics empire, while Kendall's net worth is estimated to be around $60 million, mainly from modeling and her 818 Tequila brand, making Kylie the wealthier sister by a large margin.
Kylie Jenner has stated that she gets along with Caitlyn Jenner even better than she did with Bruce, and their relationship grew much closer after Caitlyn's transition. After her transition, Caitlyn and Kylie found common ground in traditionally feminine areas, with Kylie mentioning, “We talk about makeup and clothes.
Kim Kardashian has publicly shared diagnoses and health experiences, including psoriatic arthritis, positive antibody tests for lupus/rheumatoid arthritis (leading to stress-related health concerns), and a recent brain aneurysm diagnosis linked to stress. She also speaks about her daughter North's dyslexia, advocating for parents of children with learning differences, and has faced discussions about using disabled models in her brands, sparking debates on representation and inclusion.
In fact, Caitlyn suggested their relationship changed following her transition. "Khloe, for some reason, was pissed off about something through this whole process," she said on a 2019 episode of I'm a Celebrity... Get Me Out of Here!. "Honestly, it's been five, six years and I really haven't talked to her since….
Khloe has always been the closest sister to each on of her siblings and each of the children's favorite aunt. For Khloe herself, she has always said she is closest to Rob going back to early childhood. Birth order and personality type has a lot to do with it.
"So, I wanted to ask you," Kylie said. "I know, like, sometimes people get really confused when Kendall and I still call you 'dad. ' I know we had a talk a few years ago, and you were OK with us still calling you 'dad.
They then added that "Kylie is madly in love with Timothée and she put so much into this relationship. She went so public with their romance because she was sure it would last. But those closest to her feel he doesn't make her a priority and her sisters are now telling her to walk away, but she can't."
The Kardashian-Jenner family's relationship with Caitlyn Jenner is strained and inconsistent, with Caitlyn stating she nos longer speaks to Kris or most of the stepchildren, while some, like Kim, maintain sporadic contact, highlighting a significant rift caused by past family conflicts, especially after Caitlyn's memoir, though recent family events suggest occasional, brief interactions at large gatherings.
Rob Kardashian has the lowest net worth of $10 million.
Rob also founded Arthur George Socks, which got a boost from a 2017 collaboration with the Kylie Shop, one of his youngest sister's ventures.
Today, Kendall Jenner net worth stands at $60 million. She's topped Forbes' highest-paid model list since 2017, walking for Chanel, Versace, and Balmain while her sisters built empires in beauty and shapewear.
In 2019, the magazine estimated Jenner's net worth at US$1 billion and called her the world's youngest self-made billionaire at age 21, but it turned out to be false, as Forbes revealed that Jenner and her team had deceptively forged tax-returns to create an image she was a billionaire.
“One source confirmed to me Caitlyn has made whispers of 'sex change regret,' hinting she might go back to being Bruce Jenner,” Halperin said.
“I have to compartmentalize my relationship with my Dad in a way because I love her,” Kendall said of Caitlyn in a rare confessional interview. “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.”
🔗: bit.ly/40lZh0c Editor's note: In this story, Brody Jenner uses Caitlyn Jenner's former name and pronouns, and refers to Caitlyn as "dad," which she has previously given her blessing for all of her kids to do. 📷️: Getty.
As a supermodel, Kendall Jenner is often seen as the most naturally beautiful of the Kardashian-Jenner clan.
Kourtney Kardashian has revealed that she identifies as autosexual — someone who is primarily attracted to themselves. In a recent interview, she explained that her journey toward self-love and confidence has led her to embrace this identity.
Robert George Kardashian (February 22, 1944 – September 30, 2003) was an American attorney and businessman. He gained national recognition as O. J. Simpson's friend and defense attorney during Simpson's 1995 murder trial.