Caitlyn Jenner is no doubt used to making headlines by now, given that she’s part of probably the most famous reality-show family ever and thanks to her high-profile gender transition. But when the one-time Olympic decathlete took to Instagram to post a bizarre message addressed to her youngest daughter, she left some fans in shock.
Yet it seems that Caitlyn had only intended to post a birthday message to socialite Kylie Jenner, who had just turned 22. So, as you’d expect, the star was celebrating the occasion extravagantly. Not only had Kylie ventured to Italy with her friends and family, but she was also sailing around in a superyacht that cost more than $1 million per week.
Caitlyn had apparently decided not to join in with all the fun, however, preferring instead to enjoy some downtime in her Malibu home. Yet although she wasn’t there in person, Caitlyn still risked spoiling the party with a social-media faux-pas that defined the word awkward – and left some fans shocked.
Perhaps that’s not so surprising, though, considering that controversy has seemingly followed Caitlyn around for quite some time. How come? Well, Caitlyn was born Bruce Jenner in 1949 in New Jersey and rose to fame as a sporting hero. In 1976, in fact, she won a gold medal at the Montreal Summer Olympics in the grueling event known as the decathlon. The reality star also broke the world record for the third time in a row in the process and was subsequently hailed as one of the planet’s finest athletes.
Understandably, then, Caitlyn capitalized on her Olympics glory by venturing into other areas. She appeared in a number of TV shows and movies, for example, enjoyed a brief stint in motorsports and put her name to several businesses. In 1982 Caitlyn even posed for Playgirl in what would become one of many eye-catching magazine covers.
And of course, Caitlyn became a household name once again in the mid-2000s when she joined the rest of her family in Keeping Up with the Kardashians. The E! reality series quickly became one of the most talked-about shows not only in America but across the world. It also made superstars of Caitlyn’s kids, stepchildren and wife.
At the time, you see, Caitlyn was married to Kris Kardashian. The pair had walked down the aisle together in the spring of 1991, less than half a year after they’d started dating. The couple later welcomed two daughters into the world: Kendall and Kylie. Both Caitlyn and Kris had children from earlier relationships, too.
In 1972, in fact, Caitlyn had wed Chrystie Scott, the mother of Caitlyn’s first two kids, Burt and Casey. Then, in the same week that she and Scott officially divorced in 1981, Caitlyn said “I do” to Linda Thompson at a ceremony in Hawaii. The actress later gave birth to sons Brandon and Brody – but sadly she split with Caitlyn for good in 1986.
Caitlyn then became a stepfather for the first time when she made Kris Kardashian her third wife, in 1991. After all, the socialite already had four kids from her previous marriage to lawyer Robert Kardashian: daughters Kourtney, Kim and Khloe and son Robert. But after 23 years together, Caitlyn and Kris headed for splitsville due to irreconcilable differences.
And the nature of these irreconcilable differences became apparent in April 2015 when Caitlyn told the world that she was a trans woman. The Olympian made the surprising revelation during a TV interview with 20/20’s Diane Sawyer, while also admitting that gender dysphoria was an issue that she’d struggled with all of her adult life. “For all intents and purposes, I’m a woman,” Caitlyn stated.
Caitlyn further embraced her womanhood when she famously posed for the cover of Vanity Fair later on that same year. In the process, she became the first ever openly transgender woman to appear on it. The attention-grabbing image, taken by legendary photographer Annie Leibovitz, featured the subtitle “Call me Caitlyn.”
And the response to Caitlyn’s coming out was largely positive. She was named the Teen Choice Awards’ Social Media Queen, for example, and labelled a Trans Champion by Glamour magazine, which also included her among its 25 Women of the Year. Perhaps understandably, however, Kris Jenner found her ex-husband’s transition a little harder to take.
“I’m still missing Bruce,” Kris Jenner admitted during an appearance on Radio Andy. “It’s just very confusing and complicated when you go through it this intimately with somebody. It’s really a process.” And the pair’s two daughters also appear to have initially struggled with the fact that their father is now a woman.
“My dad says it herself sometimes – it’s kind of like mourning the loss of someone, because it is,” Kendall Jenner revealed in an interview with Women’s Wear Daily. “My dad is my dad, but he’s not there physically anymore. But she lets me call her dad – that’s the last little piece of dad I’ve got.”
Kylie Jenner also told Wonderland magazine that she wasn’t particularly comfortable calling her father “mom.” She did claim, however, that she was glad that everything was now out in the open, adding, “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.”
Caitlyn Jenner’s relationship with her two daughters also reportedly became a little more strained when she published a tell-all book in 2017. “I heard about all the stuff that she was saying in it and just how a lot of it’s so not true,” Kendall complained in a subsequent Keeping Up with the Kardashians episode. “That makes no sense to me that she would go around bashing us for no reason. It’s insane, mom! That’s insane!”
Kendall later made up with Caitlyn but then became increasingly exasperated about the favoritism Caitlyn apparently displayed towards Kendall’s sister. In another KUWTK episode, for instance, Kendall visits her father at his home in Malibu – only for him to seemingly constantly talk about Kylie. She tells the cameras, “I get my dad missing hanging out with Kylie, but I do make an effort to meet up and hang out with her. She is just obsessing over Kylie and ruining the time we are spending together.”
Then, in February 2018, Kylie Jenner unexpectedly revealed that she was now the proud mother of a baby girl named Stormi. The tabloid favorite had somehow managed to keep her pregnancy a secret from everyone but her nearest and dearest, in fact. And her father didn’t seem to have been included in this particular group. After all, Caitlyn was conspicuously absent from the film clip Kylie made to document her pregnancy.
But Caitlyn prevented the rumor mill from going into overdrive just a few days later when she took to Instagram. Alongside a picture of Kylie as a tot, Caitlyn posted the message, “My daughter just had a daughter. It’s amazing to be by your side through this journey. She’s SO beautiful already. Can’t wait to watch her grow.”
Later that year, however, Caitlyn appeared to confirm in an interview with Broadly that she didn’t see her kids as much as she would like. “I spend a lot of time by myself here in the house,” she told reporter Diana Tourjee. “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.”
Caitlyn also revealed that the drama surrounding her controversial memoir hadn’t helped matters. She added, “I got the trans community out there bashing on me, I got the Kardashians out there bashing on me. All I do is sit here in the house and try to stay out of trouble.”
Despite the apparent frostiness between Caitlyn and her two kids, though, both Kendall and Kylie still took to Instagram to post Father’s Day messages in 2018. Kendall captioned her photo “the soul that raised me.” And Kylie, who uploaded a pic in which she and her sister were dressed as The Wizard of Oz’s Dorothy, told Caitlyn, “So lucky to have you.”
But tensions appeared to arise once again in 2019 when both Caitlyn and Kylie applied for trademarks for their own skincare products at the same time. The former filed a document for Jenner Skincare, in fact, while the latter wanted to launch a range named Kylie Skin. In the end, though, Caitlyn was the one who relented, allowing her daughter to go ahead with her business plans.
And thankfully there didn’t appear to be any hard feelings between the pair. In fact, Caitlyn subsequently turned up for Kylie Skin’s official launch in Los Angeles’ Goya Studios to lend her support. And she even posed alongside her daughter for a brief video clip that Kylie later posted on Instagram.
Shortly after the event, too, Caitlyn took to her own Instagram for another display of support towards her youngest daughter. Alongside an image of the Kylie Cosmetics HQ, she wrote, “20 years ago, when your mom and I were changing diapers, teaching you to walk and putting you to sleep, we had no idea this was coming. So proud. @kyliejenner.” Kylie then responded, “I love you.”
Instagram may have helped to bring Caitlyn and Kylie closer together, then. But it was also the platform via which the former very nearly – albeit accidentally – threw a spanner in the works of their relationship. The drama all began when Caitlyn took to the photo-sharing site to send a 22nd birthday message to her youngest daughter. So far, so sweet.
“Life was so simple back then, but life is so good today,” Caitlyn wrote. “Happy birthday to my little baby @KylieJenner.” This touching message was accompanied by a throwback photo in which a young and smiley girl can be seen resting her head against her father’s shoulder. But on further inspection, the image wasn’t all it seemed.
That’s because it turned out that the smiley young girl in the photo isn’t Kylie at all – but rather her sister Kendall. And several of Caitlyn’s followers soon made the one-time Olympian fully aware of her mistake. “Oh sis. You got your daughters mixed up. That’s Kendall,” commented one fan. Another remarked, “Oops! Looks like Caitlyn Jenner got Kylie and Kendall konfused!”
Caitlyn soon corrected the mistake, though, quickly replacing the offending photo with another throwback pic featuring both of his daughters. Perhaps this was to ensure that he couldn’t confuse them with each other for a second time. And Caitlyn’s social-media faux pas seems unlikely to have affected Kylie’s birthday celebrations too much, anyway.
At the time that Caitlyn posted her photo of the wrong daughter, you see, Kylie was living it up with her friends and family in Italy. Scott Disick, Sofia Richie and mother Kris were just a few of the famous names who joined Kylie on the trip. And with a $1.2-million-a-week superyacht as her base, Kylie clearly spared no expense on the shindig.
It was probably to be expected that Caitlyn wasn’t on board for Kylie’s spot of birthday yachting, too. But sister Kendall also being missing from the party celebrations was more of a surprise. On the day that the mix-up photo was posted, you see, Kendall decided to join her father for a spot of lunch at Nobu in Malibu.
Yet according to an apparent showbiz insider, Caitlyn’s Instagram error isn’t likely to have caused too much offence. The source reportedly told Hollywood Life, “Kylie is having way too much fun on her trip to be spending her energy getting upset over her dad posting the wrong baby picture. It’s also not the first time her dad has had trouble telling her and Kendall’s old baby pics apart.”
Yes, apparently Caitlyn has form when it comes to failing to spot the differences between photos of his two daughters as youngsters. The supposed insider apparently confirmed that this was very much a “dad move” and that the 22-year-old wasn’t upset in the slightest. “If anything, it was a funny reminder of her dad on her birthday,” they reportedly added.
Another source also appeared to confirm that Kylie would have seen the amusing side of her father’s faux pas. “It was really a funny moment for Kylie to laugh about,” they reportedly told Hollywood Life. “She loves her dad, and she knows it wasn’t done on purpose. It was an honest mistake that they can laugh about.”
In fact, far from getting mad, Kylie is reportedly far more interested in getting even. The same showbiz source seemingly added that “Kylie is already thinking of ideas to get her back jokingly when it is Caitlyn’s birthday in October.” And Kylie shouldn’t be short of inspiration when it comes to staging a prank.
Just a year earlier, in fact, Kim Kardashian had served as an executive producer on the Facebook prank show You Kiddin’ Me. The reality TV icon also roped in her sibling Kourtney and half-sister Kendall to help out with the first episode’s practical joke. And the poor target was none other than their mother, Kris Jenner.
Interestingly, Kris Jenner actually made her former spouse look that little bit more foolish when she posted her own birthday message for daughter Kylie. She in fact put up a throwback photo of herself as a young mother and Kylie as a toddler at a birthday party. And thankfully, she was able to choose the right daughter for the pic.
Kris’ photo was accompanied by a message that also perhaps put Caitlyn’s to shame. She began, “Happy Birthday to my baby!!! @kyliejenner I can’t believe you are 22… It is the greatest joy and blessing to be your mommy and watch you grow into such a beautiful woman inside and out.”
“You are the most amazing daughter, sister, friend and mommy… watching you with Stormi has been such a wonderful blessing,” Kris continued. “You are truly an old soul and such an inspiration to everyone. Your creativity, generosity and huge heart is truly remarkable! You are an angel girl, and I love you more than you will ever know.”
Kylie Jenner fans were subsequently given the chance to take a closer look at the star in a new Netflix documentary that premiered just two weeks after her 22nd birthday. Look Mom, I Can Fly is a behind-the-scenes glimpse into the life of her rapper boyfriend Travis Scott. Alongside several candid romantic moments between the pair, then, the film also shows how they’ve both adapted to parenthood.