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She started modeling young -

Her first modeling job was a campaign for Forever 21. She made her New York Fashion Week debut modeling for Marc Jacobs in 2014, and has been in the modeling industry since she was 14 years old.

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Karl Lagerfeld had no clue who she was -

Jenner landed a show with Chanel, and though many thought her modeling career was due to 'Keeping Up with the Kardashians,' Karl Lagerfeld told Harper's Bazaar: "No, we don't have it here. I didn't even know she was in it. I saw it when it was only her sisters and she was, like, a baby."

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She dropped out of school to be homeschooled -

When her modeling career took off, it became impossible for her to physically attend school. Still, she completed her high school degree in 2014.

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She suffers from trypophobia -

Trypophobia is the fear of clusters of small holes in irregular patterns. In one of her blog posts, she wrote that things like pancakes, honeycomb, or lotus heads were common triggers. She said that she can't even look at the little holes because they give her anxiety.

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Dating Harry Styles -

Jenner's first real publicity started when she famously dated Harry Styles around 2014, back when he was still a member of One Direction. The two have remained friends since breaking up, and reunited when Styles was the guest host of 'The Late Late Show with James Corden' where they played 'Spill Your Guts or Fill Your Guts.'

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Quick flings -

Jenner and Nick Jonas had a brief fling in the summer of 2015 after being set up by her friend Gigi Hadid and his brother Joe Jonas, who were dating at the time. She also reportedly had a fling with A$AP Rocky in July 2016.

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She's a horse girl -

"I'm a horse girl, literally. I grew up riding horses," she told The Cut in 2019. "So for my whole entire life I would beg my parents to please get me a pony … It was my life. I ate, breathed, and slept horses. And I wanted one so bad." She named the pony she received for her 12th birthday Megan, and thought for a while that she would be a professional horseback rider.

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The infamous Pepsi ad -

Pepsi campaigns have featured celebrities such as Michael Jackson, Robbie Williams, Beyoncé, David Beckham, Lionel Messi, and many more, so it's almost an honor to be offered a commercial. Jenner had the chance in 2017 after making a name for herself as a model, but it couldn't have gone worse…

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The infamous Pepsi ad -

In the Pepsi ad, Jenner leaves a photoshoot to join protesters calling for peace, then walks up to a police officer in the barricade and hands one a can of Pepsi. He smiles and the crowd cheers, but off-screen huge waves of backlash came soon after, criticizing the ad for centering a privileged, white model as the peacemaker between civil rights activists and police, and for undermining the Black Lives Matter movement.

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The ad was pulled -

Pepsi pulled the advert less than 24 hours after releasing it, apologizing for its unintended effect. Jenner, however, was silent until she spoke about it on 'Keeping Up with the Kardashians.'

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Her tearful moment -

In a tearful confessional during the season 14 premiere, Jenner expressed regret. "If I knew this was gonna be the outcome I would have never done something like this," she said, explaining that she'd "never purposely hurt someone" and that "I feel really bad that anyone was ever offended. I feel really bad that this was taken such a wrong way and I genuinely feel like s—t."

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That didn't cut it -

Many who watched the tearful confession of regret felt that Jenner's tears were unhelpful and insufficient. They said that instead of actually apologizing and acknowledging the harm of her actions and committing to learn about it, she just spoke about how her own life was "ruined."

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Her affinity for basketball players -

Jenner reportedly dated point guard Blake Griffin from September 2017 to March 2018, then point guard Ben Simmons on and off from May 2018 to May 2019, and since June 2020 she's been happily with Devin Booker.

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She doesn't like to discuss her love life in public -

That's why her relationships have largely all been off-camera, from her family's reality TV show as well as the paparazzi.

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Her first kiss was in the bathroom -

In a big TV family, she needed to find some privacy behind a locked door for her first kiss. She explained to W Magazine: "It was in a shower, but not on. We were fully clothed playing truth or dare and it was me and three of my friends. And my little sister was trying to spy on us. My room didn't have a lock on it, but the bathroom door did so we all shoved in the bathroom until when we got dared to kiss someone. We would have to go in the shower and like close the curtain so no one would see and we'd kiss and come out."

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She's learning about herself through others -

"I think you learn different lessons in every relationship," the model said in a behind-the-scenes video for her Calvin Klein campaign in February 2020. She added: "A lot of the relationships have taught me more about myself, which is the most valuable. And like, what I want from a person or from a relationship."

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Her own line of tequila -

In 2021, Jenner launched her 818 Tequila brand, which had already picked up various awards and boasted a hand-crafted experience, and which had Jenner herself as its brand ambassador. It had immediate celebrity support, but it didn't fare so well online...

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Controversy -

Many people criticized Jenner for ripping off a precious Mexican commodity passed down through families and tradition, taking credit for and getting rich on a tequila that is sacred to the Mexican region and a culture that isn't her own.

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Another controversial ad -

Not only that, but Jenner was in another controversial ad campaign promoting the tequila, with her hair in two long pigtail braids, riding a horse through an agave farm, thriving while a number of workers were pictured in the background. Besides the obvious, many felt it was also an example of cultural appropriation—something her sisters are often accused of.

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Damage control -

Realizing she had to act quickly to change the negative connotation attached to her brand, Jenner announced a few weeks later on the 'Tonight Show Starring Jimmy Fallon' that the agave waste is being turned into sustainable bricks that they will be donating back to the community of Jalisco to build homes and a hospital. Additionally, 818 Tequila partnered with 1% For the Planet to "donate 1% of our profit to planet-saving initiatives."

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She loves interior design -

According to Architectural Digest, Jenner's design team—the mother-and-son duo Kathleen and Tommy Clements, plus Waldo Fernandez—were surprised by her mood board. "Her taste was surprising, more bohemian and funky than the rest of her family. The mood she described was totally understated and down-to-earth," Tommy recalled.

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She loves cars -

As the highest-paid model in the world, she can afford to indulge in her passion for cars, a collection which reportedly includes a 1957 Chevrolet Corvette Convertible, a Range Rover, a 1969 Chevy Camaro SS Convertible, a Ferrari 488 Spider, a 1960s Cadillac Eldorado, a 1965 Ford Mustang Convertible, and more.

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She once got a Rolls-Royce from a stranger -

For her 21st birthday, she got quite the unexpected gift. "We go outside and there's this Rolls-Royce," Khloé Kardashian told Jimmy Kimmel, "and this man standing there. I was like, 'What's the gift, the guy or the car?' And then this guy just hands Kendall a pair of keys to this car and I was like, 'Do we even know who this guy is?' I was like, 'Is this a joke?' On my 21st birthday I got like, dinner and a purse. I didn't know you get cars from strangers."

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Opening up about her mental health -

Jenner has spoken publicly about her experience with anxiety and panic attacks in 2016, 2018, and again in May 2021 with Vogue. Sitting down with clinical psychologist Ramani Durvasula, she explained why she's sometimes hesitant to share due to her privilege. "I'll never sit here and say that I'm not fortunate. I know I live a very privileged, amazing lifestyle—I'm a very blessed girl," she said, but added, "No matter what someone has or doesn't have, it doesn't mean that they don't have real-life feelings and emotions."

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Panic attacks -

"I think being overworked and being in the situation that I'm in now is kinda what set it out of control in a way," Jenner said of her anxiety. "I've had times where I feel like I need to be rushed to the hospital because I think that my heart's failing and I can't breathe and I need someone to help me."

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She and Gigi Hadid are closer than best friends -

The best friends have been close for their entire careers, and they're actually connected through the family! Hadid's former stepfather David Foster was once married to Linda Thompson, who was previously married to Caitlyn Jenner.

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She has a scary amount of alleged stalkers -

In early April 2021, the model got a restraining order against an alleged stalker, 27-year-old Shaquan King, who was caught swimming naked in her pool while she was home.

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She has a scary amount of alleged stalkers -

Earlier that week, Jenner was granted a temporary restraining order against another man, 24-year-old Malik Bowker, who allegedly traveled across the country to gun her down. According to TMZ, an LAPD detective alerted the model that Bowker, who had been placed in a psychiatric ward, could be released soon, and that he had previously expressed plans to buy an illegal firearm to shoot the model and then himself.

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She hates public speaking -

In her Vogue 'Open Minded' series, she confessed that she has a lot of anticipatory anxiety about public speaking. She alluded to the times she messed up, including at the 2014 Billboard Music Awards when she struggled to introduce 5 Seconds of Summer and seemed to try to duck out of the frame. "Guys, I'm the worst reader," she said with an embarrassed laugh before stumbling some more.

Sources: (BBC) (People) (The Richest) (Architectural Digest) (Vogue) (Harper's Bazaar) (W Magazine) (Hot Cars)

See also: The biggest award show blunders

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