What Caitlyn's Relationship Is Like With The Kardashian/Jenner Sisters Today

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Former Olympian Bruce Jenner (now known as Caitlyn Jenner following her transition in 2015), wed momager extraordinaire Kris Jenner in April 1991. Through this union, Caitlyn became stepdad to Kris' teenagers, Kourtney and Kim Kardashian, and her younger children, Khloé and Rob Kardashian. Although the couple endured a few road bumps that can be common among blended families (Caitlyn had four kids prior to wedding the businesswoman), the Kardashians quickly grew close to their adopted father figure. And the fam's bond became that much deeper when Caitlyn and Kris welcomed Kendall Jenner in 1995 and then Kylie Jenner in 1997.

After several years of portraying a happy family unit on Keeping Up with the Kardashians, Kris and Caitlyn announced their separation in October 2013. The family naturally took sides, a rift that intensified when the pair formally divorced in 2014. But wait — the drama didn't stop there. Some kids expressed feeling blindsided the following year, when Caitlyn announced her plans to transition into a woman. While all of the kids were supportive of Caitlyn's decision, some felt that she could have been more forthcoming about the timeline.

Oh, and let's not forget Caitlyn's 2017 tell-all book, The Secrets of My Life. The project didn't sit well with the famous sisters due to her not-so-flattering portrayal of Kris and their marriage. Talk about major drama.

So, has Caitlyn since mended fences with her family? Here's the real deal on what Caitlyn's relationship is like with the Kardashian/Jenner sisters today.

She's 'closer' to the Jenner side

Before marrying Kris Jenner, Caitlyn Jenner fathered four children: Casey and Burt Jenner with ex-wife Chrystie Crownover, and Brandon and Brody Jenner with ex-wife Linda Thompson. It's no secret Jenner's relationship with her first four children was rocky throughout the years, all the way from estrangements to public feuds. But has this since changed?

Per Caitlyn, she's bonded with her formerly estranged kids, noting that the tables have turned since her transition in 2015. The former athlete revealed the tidbit in December 2018 during a WEtv panel discussion in which she was asked about her relationship with the Kardashian clan. "My relationship is good with them," she replied (via TooFab), adding,"I mean, everybody's so busy. Of course, you wanna be with everyone every day because that's what you did your entire life, but Kylie's busy, Kendall's running all over the world, this and that. But my relationship is still good with all of them."

She continued: "Same with the Jenner side. Actually, lately, I've probably been a lot closer to the Jenner side — my son, Brandon. Brody, somewhat. Burt, all those kids. My daughter, Casey, we've actually been really very good over the last year. We happened to get a lot closer. She's got three kids and doing just great."

We don't know about you guys, but we're thrilled to learn that Caitlyn's relationship with the Jenners is back on track.

Caitlyn thinks the world of Kim

Kim Kardashian was one of the most supportive family members when it came to Caitlyn's transition, from doling out fashion advice to helping the sports enthusiast in perfecting her "best feminine voice." The mogul also praised Caitlyn's Vanity Fair cover, telling Entertainment Tonight: "She's beautiful, and I'm so proud that she can just be her authentic self. I guess that's what life is about." Aww.

Sadly, Kim's good will deteriorated when Caitlyn wrote her tell-all book, in which she criticized her ex-wife Kris Jenner. The reality star was none too pleased with her stepdad's actions, going as far to bash her past divorces and relationships on an episode of Keeping Up with the Kardashians. "She just literally started three families with three different people and f***ed everyone over," the mom fumed. Ouch to the billionth degree, right?

Despite the pair's issues, Caitlyn isn't afraid to give credit where it's due. "You take Kimberly ... She has been doing this show for, like, 12, 13, years now and has stayed relevant," Caitlyn said in December 2018 about her stepdaughter's shrewd business acumen (via Us Weekly). "You see actors come in and do their job and they're relevant for one show or one movie and then you don't see them for three years. Kimberly's been out there; she's extremely smart." Yep, we think it's safe to say Caitlyn will always admire Kim.

It's all good with Kanye

It's no secret that Kim Kardashian deeply values her relationship with her husband, rapper Kanye West. So, we're not too surprised that some fans are curious about how Ye's friendship with Caitlyn Jenner has faired throughout the stepdad and stepdaughter's ups and downs. As it turns out? West has seemingly maintained a friendly rapport with Caitlyn and her rumored girlfriend, Sophia Hutchins, as evidenced by a text exchange shared to Twitter in August 2018.

To sum up the since-deleted message shared by West in a nutshell, Caitlyn had sent the rapper a picture of Hutchins modeling his fashion line, Yeezy, against the backdrop of a sunset. "Sophia loved the first set of looks your team left and went all yeezy for her travel outfit today! We love your looks!! Thanks again," Caitlyn supposedly wrote (via People), to which West replied, "So awesome. Your [sic] welcome."

Oh, and did we mention Caitlyn's gushing birthday post to West in June 2019? "Not only is he an extremely talented artist, he is an amazing husband to Kim, and father to his children," she penned on Instagram. "I am so blessed to have you in my life, Kanye."

West and Caitlyn might not trade BFF bracelets anytime soon, but it seems like they've remained tight despite the drama. Way to stay on Ye's good side, girl.

Caitlyn is allegedly using Khloé

One of the more darker rumors about Caitlyn Jenner's relationship with Khloé Kardashian revolves around fame and the ex-Olympian's reported desire to reconnect with the Kardashians. Considering Khloé is the pseudo gatekeeper of her family, Caitlyn supposedly targeted her stepdaughter as a way back into the Kardashian's good graces. "As much as she may deny it, Cait would love nothing more than to be welcomed back into the Kardashian fold," an insider told Radar Online about Caitlyn's supposed desperation. 

Making matters even more uncomfortable? Caitlyn supposedly swooped in during a hard time in Khloé's life. Supposedly thinking it would be a "perfect time to extend an olive branch," Caitlyn reached out to Khloé in the aftermath of her then-boyfriend, Tristan Thompson's alleged cheating scandal. To do so, the former reality star supposedly sent flowers, a personalized note and a promise to Khloé's "helpline."

We have a hard time buying that Caitlyn would ever be diabolical as to use such a gesture for ulterior motives, but you never know.

How Khloé really feels about Caitlyn's rumored GF

When you push Khloé Kardashian's buttons, she isn't afraid to let you know. Want some proof? Look no further than comments she made about her stepdad, Caitlyn Jenner, in a May 2016 episode of Keeping Up with the Kardashians. Khloé accused Caitlyn of instigating their explosive fight when she trash-talked Kris Jenner in the media. The whole ugly meltdown propelled Khloé to cut ties. "She can tell me to f**k off all she wants," she said (via Mic). "I don't have a relationship with her. I'm done." Woah, tell us how you really feel.

The good news? Things have seemingly since thawed a bit between the two, with Caitlyn's rumored girlfriend, Sophia Hutchins, possibly being the catalyst. The topic came up during a May 2019 episode of divorce attorney Laura Wasser's podcast, Divorce Sucks!, when Khloé was asked whether Caitlyn was currently dating a female. "Yes, I believe that she is a transgendered woman as well," Khloé responded. "She's really, really sweet, too. She's really sweet. She's younger but like, she's not bothering anyone. She's super sweet."

Hmm, could this mean that Khloé and Caitlyn are on the mend? If she's familiar with Hutchins, then it's possible the trio had a get-together. We guess we'll have to wait and see how this one turns out.

Did Kourtney call a truce?

Countless southern California residents endured a frightening few weeks in November 2018, when wildfires spread throughout the Calabasas, Malibu, and Hidden Hills areas, to name a few locations. Multiple members of the Kardashian/Jenner family were forced to evacuate their homes, including Kourtney Kardashian and Caitlyn Jenner. Although the two were physically unharmed (what a relief, right?) the situation was incredibly difficult, and both parties reflected on the widespread devastation in their beloved neighborhoods.  

Interestingly enough, the harrowing chain of events reportedly inspired Kourtney to make amends with Caitlyn for the sake of her three children. "Both of Scott's parents are dead and Kourtney thinks it's really important for her kids to have grandparents in their lives," an insider told Radar Online"Kourtney was of course bothered by what Caitlyn did to her mom. But Kourtney has been over Kris lately and her loyalty is to no one, except for Kim."

We can't say whether this report is accurate, but it's possible there's some truth to it because Caitlyn wrote a glowing birthday post for Kourt's birthday in April 2019. "It has been one of the greatest joys in my life to watch you grow in so many ways," she wrote on Instagram. "You are an amazing mom to your kids. You are an amazing business woman. And above all else a kind soul."

Fingers crossed the two truly patched things up — we'd love to see Caitlyn develop a strong bond with grandkids Mason, Penelope, and Reign. 

Breaking down her relationship with Kendall

An upsetting rumor about Kendall Jenner and her dad, Caitlyn Jenner, surfaced in September 2018 when a source supposedly spotted the pair fighting at a posh restaurant in Malibu. "They were arguing . . . It was more Kendall ripping Caitlyn a new one for 'always turning her back on the family' after they've been so good to her," the source told Page Six. Color us intrigued, y'all.

Just months after the supposed altercation, however, the two posed alongside one another at Vanity Fair's Oscars party (above) in February 2019. The father and daughter looked thrilled as they hugged and flashed their pearly whites for the paparazzi, suggesting that their supposed spat never happened or was in the past.

Adding more fuel to this theory? Caitlyn had high praise for Kendall's talents, telling E! News during the red carpet event: "She's so good at what she does. I don't know if she wants to do [acting] yet, 'cause she's so successful at modeling. But at some point, I think she should do that, and I think she'd be very good at it."

Spoken like a true dad, right?

About that makeup debacle...

There's little debate surrounding Kylie Jenner's success as a makeup mogul — girl runs Kylie Cosmetics, after all, a company worth an estimated 900 million. Wowza. And while Kylie is the queen of beauty in her family, another member supposedly tried to steal her throne — dad Caitlyn Jenner. It all started when the former athlete filed trademark applications to the U.S. Patent & Trademark Office for "Jenner Skincare" and "Skincare By Jenner," registrations that suggested a skincare line was in the works. The problem? The U.S. Patent & Trademark office denied the applications because the names were too similar to Kylie, Kendall Jenner, and Kris Jenner's trademarks. We got to ask... why didn't Caitlyn foresee that happening? 

Shortly after the applications were nixed, Caitlyn dropped the process altogether. We're not sure if she lost inspiration for the business venture or whether her famous fam put the kibosh on the supposed plan.

Either way, Caitlyn isn't a sore sport — she showed up to support Kylie at her launch of Kylie Skin (above) in May 2019. Way to be an encouraging poppa, Caitlyn.

She's in awe of Kylie's parenting

Makeup mogul Kylie Jenner welcomed her adorable daughter, Stormi Webster, in February 2018. Although some people questioned Kylie's parenting abilities given her young age of 20, Caitlyn Jenner isn't one of them. In fact, Kylie's loving dad, who sang her daughter's praises in honor of Stormi's 1st birthday party in February 2019. "Beyond proud of my amazing daughter for all of her accomplishments, but especially proud of what an amazing mom she is to her little girl!" Caitlyn penned on Instagram, captioning a series of sweet shots featuring Kylie, Stormi, Caitlyn, and her rumored girlfriend, Sophia Hutchins. Too cute.

But if you're wondering whether it took Caitlyn a long time to come around to Kylie's pregnancy, the answer is seemingly no. Despite the fact that the ex-athlete is a bit traditional, she reasoned that Kylie would be OK no matter what. "She's always wanted to be a mom but when she called me up it was a bit tough for her because, obviously, she's not been married," Caitlyn said on the UK chat show Loose Women in September 2018 (via People). "But [Kylie] wanted to start a family, she wanted to start it young. Fortunately, she's in a position where she can have a child and the child will be well taken care of."

It's pretty wonderful that Caitlyn has been by Kylie's side through her pregnancy and transition into parenthood. 

Dad or mom?

When a person transitions, it's not uncommon for them to change their name or personal identifiers. This exact topic came up when Caitlyn Jenner transitioned in 2015, with some fans wondering whether she'd change her identity from "dad" to "mom." If you believe a March 2018 report from Radar Online, Caitlyn was always hopeful that her kids would opt for mom instead of dad — a switch that supposedly never happened. "Her own daughters, Kendall and Kylie, still refuse to call her 'mom,'" the insider said. "They call her 'dad' and it drives Caitlyn crazy. "She understands why her stepkids wouldn't, but she's told her daughters to please not call her 'dad' anymore. She's sick and tired of it."

But before you buy the hype, check out what Caitlyn said about the situation during an interview with Bravo exec Andy Cohen in April 2017. When asked how she feels about some of the kids "missing Bruce," Caitlyn replied: "I am a dad. I tell them to call me dad. I have no problem with that."

Of course, each person's journey is different. You have to do what's right for your comfortability at the end of the day.