Strange Things About Kylie And Kendall's Relationship With Caitlyn

When Olympic gold medal winner Bruce Jenner announced that he had decided to transition into a female and go by the name Caitlyn, the news came as a shock to everyone, including the majority of his famous family. Jenner has experienced many highs and just as many lows since becoming a woman. She was named Glamour's Transgender Champion at the 2015 Women of the Year awards, a wonderful moment of recognition for her. Not every female has been supportive of the reality star, however. Actress Rose McGowan hit out at Jenner after she proclaimed that "the hardest part about being a woman is figuring out what to wear," and even members of Caitlyn's own family have had some stern words for her.

Caitlyn's relationship with ex-wife Kris Jenner and her star step-daughter Kim Kardashian has become increasingly strained in recent years, but what about her two biological daughters? Kendall and Kylie Jenner have been on a roller coaster ride of their own ever since Caitlyn announced her arrival, and now it appears as though they're stuck between the warring Kardashian-Jenner factions of the family. But which side have they taken? Have they really accepted Caitlyn for who she is? Let's take a look at all the strange things about their extremely complicated relationship.

Not long after the transition announcement, Caitlyn decided to go it alone and front her own show, I Am Cait. The eight-part documentary series (which aired for two seasons between 2015 and 2016) followed Jenner as she adjusted to life as a woman and gave viewers a front-row seat to all the ensuing family drama. The show contained several tense moments between Caitlyn and ex-wife Kris Jenner, including an argument over the former failing to get an invite to daughter Kylie's graduation ceremony.

"It wasn't me making that decision, it was you making that decision," Caitlyn told Kris (via Female First), pinning the snub on her. "I was so disappointed in everybody. For 15 years of my life, I carpooled the kids every day. Some days, I would spend three or four hours in the car. [It's] a slap in the face when you don't even get invited to their graduation."

Kris was quick to hit back, claiming that she too had felt betrayed when Caitlyn said that she had been "mistreated" during their marriage in an interview with Vanity Fair. "That's exactly how I felt," she snapped. "Because I spent 25 years of my life and 18 hours a day and blah blah blah... Listen, usually people that get a divorce don't do everything together. It wasn't malicious, it didn't intend to hurt anybody's feelings, but my feelings still weren't healed."

Most of the Kardashian-Jenner clan appeared to be just as shocked as the rest of us when Bruce Jenner declared his intention to transition, but Kendall Jenner later admitted that she actually knew her dad identified as a woman deep down. "I've known since I was a kid," she told Women's Wear Daily (via Look). "He never confirmed it to me, but I've known for a very long time." The reality star and model revealed that she and her sister Kylie Jenner began to suspect that something was up after they discovered some wigs, but it wasn't until she accidentally came across her dad in full cross-dress that she understood the extent of it all.

"She would wake up really early just so she could dress up and move around the house and get that little kick for the morning, and then go back to being Bruce," Kendall said (via the Daily Mail). On one particular day she got out of bed at 4 a.m. and went downstairs for a glass of water, which was when she saw Caitlyn for the first time. "My dad was coming down the stairs in, like, a wig and makeup and shoes, the full nine. She didn't see me. I literally froze." A stunned Kendall managed to hide herself to the left of the staircase, avoiding an awkward meeting. "Thank God she turned right and, to this day, has no idea that happened. That was the first time I had ever seen her."

Kendall Jenner has likened her dad's transition into a female to the death of a family member. That bleak outlook might seem like she's throwing shade at her father to an outsider, but it's an assessment that Caitlyn herself actually agrees with. "My dad says it herself sometimes, it's kind of like mourning the loss of someone, because it is. My dad is my dad, but he's not there physically anymore," she told Women's Wear Daily (via Look). "But she lets me call her dad — that's the last little piece of dad I've got."

Kylie Jenner has also refused to call Caitlyn "mom" as it just doesn't feel right to her. "I could call her mom, I'm not against it, I'm just saying it's not correct," she told Wonderland magazine (via The Sun). The youngest star of Keeping Up with the Kardashians also confirmed that she was well aware of her dad's struggles with gender identity from a young age, but she simply went along with the lie like everyone else. "I mean, I obviously knew about it my whole life, but it was never admitted to and then when it was all said and done, I honestly just wanted not to be lied to. I'm OK with everything, as long as everyone is honest."

Both girls wished Caitlyn a happy Fathers Day in 2018, posting throwback photos of them together. Kendall captioned hers "to the soul that raised me," while Kylie wrote "so lucky to have you."

Kendall Jenner's epic announcing fail at the 2014 Billboard Music Awards became one of the talking points of the event. The teen was tasked with introducing Australian boy band 5 Seconds of Summer, but she had some "teleprompter issues" and almost called them One Direction during a super-cringe-worthy intro. Despite the debacle, Billboard invited Kendall and sister Kylie Jenner back the following year, but once again it proved to be a nightmare evening for her.

Caitlyn Jenner had come out to the world just weeks before the 2015 BBMAs, and (fearing that the media would grill her about her dad's gender transition) Kendall decided to skip out on press interviews and basically left younger sister Kylie to deal with the media circus. In footage shown on Keeping Up with the Kardashians (via the Mirror), Kylie tells her publicist that she is about to pass out before she too backs out and leaves.

"Wait, no, now I feel too sick," Kylie can be heard saying as she lingers at the red carpet area. "I feel like I'm going to faint. I really don't want to." Back at home, the younger Jenner let her big sis know exactly how she felt about being ditched. "I totally understand you had your s*** going on, I just felt like I really needed you." Kylie also complained about Kendall's shady move to half-sister Kim Kardashian. "I was looking around for Kendall and she wasn't there," she said. "I didn't know what to say."

According to reports, Kendall and Kylie Jenner's relationship with Caitlyn became strained after the release of the latter's tell-all memoir, The Secrets of My Life. The book was full of revelations about Jenner's days (she even touches on the O.J. Simpson trial), but it also went into great detail about the rise of the Kardashians.

According to Time, The Secrets of my Life reinforces the image of Bruce Jenner as a "steamrolled dad" who had little say in anything, and going after Kris in this way apparently alienated Caitlyn from the rest of the family, all except for his youngest daughter. As her sister sided with their momager, Kylie (who met Caitlyn for the first time on an episode of her show I Am Cait) tried to play peacekeeper.

"Kendall is loyal to Kris and has very little to do with her dad," an insider revealed to E! News. "The more time that has passed, the more she feels Caitlyn has let her down with the things she has said and with her actions. Kylie has really made an effort not to take sides and to be supportive of Caitlyn." The source went on to claim that the way in which Caitlyn has "hurt Kris tremendously" has made it very difficult for Kylie to keep the peace. "With everyone in the family on Kris' side, it's hard on Kylie. She tries to keep it separate and doesn't want to discuss it with the rest of the family."

When Kendall reacted to Caitlyn's controversial memoir on a 2017 episode of Keeping Up with the Kardashians, she reacted strongly. The outraged model simply couldn't believe all the things that her dad had written about her mom, calling her allegations "insane" as she ranted about the book to Kris Jenner. "I heard about all the stuff that she was saying in it and just how a lot of it's so not true," she said.

A disappointed Kris said that Caitlyn could have handled the memoir in a more positive way and reminded Kendall that her kids will grow up and read these "lies" and "fabrications" about their family. "You're right," Kendall agreed. "And then she goes around dissing the Kardashians, but it's like, those are the kids that you raised! If you have a problem with them, you raised them. That makes no sense to me that she would go around bashing us for no reason. It's insane, mom! That's insane!"

The backlash from her family (Kim Kardashian openly accused her of being a "liar" after reading her book) turned Caitlyn into a recluse. During her interview with Broadly, the gold medalist admitted that she spends most of her time home alone nowadays. "I spend a lot of time by myself here in the house," she said. "I have a lot of children, but sometimes just because of circumstances, maintaining a close relationship with your kids is very tough. They all have lives. They've all moved on."

While she was said to have initially sided with Kris after the release of her father's memoir, Kendall soon began visiting her dad at her Malibu home. Caitlyn invited both of her daughters over so they could check out some horses together (she had a barn built in the hope that the pair would visit more), but on this occasion only Kendall turned up. Not content with that, Caitlyn proceeded to incessantly talk about Kylie, and the topic of conversation began to wear Kendall's patience thin.

"You talk about it a lot," she told Caitlyn (via the Daily Mail). "I am here. I am not good enough?" The model then complained about her father to the Keeping Up with the Kardashians cameras, telling the viewers that Caitlyn's behavior was not only insulting, but a little obsessive. "I get my dad missing hanging out with Kylie but I do make an effort to meet up and hang out with her," she said. "She is just obsessing over Kylie and ruining the time we are spending together."

Kendall eventually snapped and confronted her dad, warning Caitlyn that she was running the risk of driving her away. "You keep complaining and it is making me not even want to be around you," Kendall said. True to her word, Kendall seemed to distance herself over the next year, with Page Six noting that she was "oddly reluctant" to be photographed with her father on the red carpet of Vanity Fair's 2018 Oscar party.

When Kylie announced she'd given birth to a baby girl in February 2018, the news came as something of a shock. The 20-year-old apologized for keeping fans in the dark about her pregnancy, explaining that this was a journey she only wanted to share with a few select people. Caitlyn Jenner apparently wasn't one of those people. After giving birth to baby Stormi, Kylie released an 11-minute video montage of her pregnancy that featured several members of her family, but Caitlyn was nowhere to be seen.

Her absence from the video got the rumor mill going once again, with many assuming that Kylie and Caitlyn were no longer on good terms. It later transpired that Caitlyn was not only absent during the pregnancy, but had missed the birth itself. "There was never even the slightest chance that Caitlyn would be there at the hospital when Kylie gave birth, it would have just caused all kinds of problems with Kris and the other Kardashian girls," a source close to the former Olympic athlete told Hollywood Life.

Caitlyn was actually in Ireland on a work-related trip at the time, but even if she had been at home she wouldn't have been invited, the insider claimed. "Kylie and Caitlyn's relationship has been a little frosty of late, as she made it clear she didn't approve of Kylie having a baby at her age when she wasn't in a committed relationship, but Kylie hopes that will change when Caitlyn meets the new arrival."

Jenner has denied that there is anything more than friendship going on between her and transgender beauty Sophia Hutchins, but rumors of a romance persist nonetheless. In fact, sources are claiming that the reality TV star and Hutchins (who have been spotted vacationing in both Mexico and London together) are actually engaged. "Caitlyn really sees herself spending the rest of her life with Sophia," a source close to Jenner told Heat magazine (via the Mirror). "She lost her support system when she fell out with her family and these days, it feels like Sophia's the only person she can count on."

The thought of having a step-mom who is the same age as Kendall apparently has both Kendall and Kylie beside themselves with worry. Speaking to Life and Style magazine, a second source claimed that the Jenner sisters were suspicious about Hutchins' (who was named Scott pre-transition) intentions when it comes to their dad. "They've heard from friends that Caitlyn's dating Sophia, and it upsets them like you wouldn't believe," the insider dished. "She's their age! They feel a mix of jealousy and distrust about it."

Hutchins (who is 42 years younger than Caitlyn) attended Malibu's Pepperdine University, which is located close to Caitlyn's house. Judging from her Instagram, Caitlyn's house is where Hutchins actually spends most of her time nowadays. She regularly uploads from the swanky $3.5 million property, and Caitlyn is "barely able to be photographed without Sophia by her side," according to Elle.