Kylie Jenner’s nearly every move has been under a microscope thanks to growing up in front of cameras on “Keeping Up With the Kardashians.”
And her love life is no different.
From her teenage flings with Jaden Smith and Cody Simpson to welcoming two kids with Travis Scott, the makeup mogul’s relationships have been well-documented in the media over the years.
Of course, that also includes her latest romance with actor Timothée Chalamet, which reportedly began in April 2023.
Here’s a look back at Jenner’s dating history.
Cody Simpson
The Kylie Cosmetics founder dated the Australian musician-turned-competitive swimmer when they were both navigating their growing fame as 14-year-olds.
The pair first met at the world premiere of “The Twilight Saga: Breaking Dawn – Part 1” in November 2011 when Kylie and her older sister Kendall Jenner interviewed Simpson for “On Air With Ryan Seacrest.”
Sparks immediately flew when the reality TV star introduced herself and told him that he’s her “rumor boyfriend on Twitter.”
Afterward, the “All Day” singer tweeted that he “had a real good time” meeting the sisters. “see ya soon I hope!” he added.
A source later claimed to Us Weekly (via E! News) that they were definitely a couple.
However, Kylie later denied the romance rumors.
“Cody and I are just good friends. That’s it,” she told Seventeen (via Us Weekly) in July 2012. “We can say that as much as we want and people will still listen to gossip.”
Simpson went on to date Gigi Hadid on and off between 2013 and 2015 and Miley Cyrus for about 10 months between 2019 and 2020.
Jaden Smith
The Kylie Skin founder reportedly began dating Will Smith and Jada Pinkett Smith’s son, Jaden Smith, in 2013.
Although they were spotted holding hands after a movie date in June of that year, she also slammed speculation that they were romantically involved on Twitter.
“Media always making it seem like I’m dating everyone I’m seen with.. Makes no sense to me. Don’t listen to everything u see, people,” Kylie tweeted at the time.
But the rumors reignited when she brought Jaden as her date to older sister Kim Kardashian’s lavish Italian wedding to Kanye West in 2014, where the two were reportedly spotted “making out” at the reception.
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Despite eventually ending their teenage love story, Kylie and Jaden have continued to hang out as friends over the years, including at Justin Bieber’s 2018 nuptials to Hailey Bieber and at Kendall’s 25th birthday party in 2020.
Lil Twist
While she was still linked to Jaden, Kylie was also seen out with rapper Lil Twist on a one-on-one movie date in Calabasas, Calif., in July 2013.
The pair shared flirty exchange on Twitter the following year, though nothing further appeared to happen with their connection.
Tyga
The youngest Kardashian-Jenner sister’s first high-profile romance was with rapper Tyga, whom she began dating two years after they met at her 16th birthday bash.
He also hosted her 17th birthday party at his Los Angeles mansion.
The pair’s age difference quickly became a topic of conversation, considering they went public with their relationship around Kylie’s 18th birthday in August 2015 when the rapper was 25.
Plus, Tyga was already a father to his son, King Cairo, whom he shares with ex-fiancée Blac Chyna.
The duo traveled around the world together during their on-again, off-again relationship, even proving how serious when Kylie showed off a promise ring from the “Rack City” hitmaker in September 2016.
However, the pair called it quits for good in April 2017.
Following the split, Kylie revealed that she was simply ready to move on.
“There was absolutely not one thing wrong with me and T. He and I will always, always have a bond,” she said on her short-lived reality show, “Life of Kylie,” per People.
“There was no crazy fight, we just decided … Well, I decided that I’m really young. I don’t want to look back five years from now and feel like he took something from me when he’s really not that type of person.”
Travis Scott
The “Kardashians” star first sparked dating rumors with Travis Scott when they were caught getting cozy at Coachella in April 2017. They made several public appearances together within the following weeks.
The following year, Kylie reflected on the beginning stages of their romance, telling GQ, “He said, ‘I’m going back on tour — what do we want to do about this?’ Because we obviously liked each other.”
“And I was like, ‘I guess I’m going with you’ … And then we rode off into the sunset,” she added.
Their relationship quickly became serious when Page Six confirmed in September 2017 that Kylie was pregnant with their first child.
She and the “Sicko Mode” musician welcomed daughter Stormi Webster in February 2018 after keeping the pregnancy under wraps for months.
“I’m sorry for keeping you in the dark through all the assumptions,” the reality star tweeted at the time. “I knew for myself I needed to prepare for this role of a lifetime in the most positive, stress free, and healthy way I knew how.”
The Kylie Baby founder and the Houston-born artist later made their red carpet debut at the Met Gala in May 2018.
And in 2019, the proud parents took Stormi to her first red carpet for the premiere of the rapper’s Netflix documentary, “Travis Scott: Look Mom I Can Fly.”
But despite looking like the picture-perfect family, the pair decided to take a break from their love in October 2019.
“They are taking some time but not done,” a source close to Kylie told People at the time. “They still have some trust issues but their problems have stemmed more from the stress of their lifestyles.”
The cosmetics entrepreneur duo confirmed they were back together in May 2021 when she shut down rumors about being in an open relationship.
Just months later, Page Six exclusively reported that Kylie and Scott were expecting their second child together and that her family was “thrilled.”
They welcomed their baby boy in February 2022.
Although their son’s name was originally Wolf Webster, Kylie announced that his new name was Aire in January 2023.
However, by that point, she and Scott had already broken up again — seemingly for good.
Scott spent Halloween 2022 partying at a club in Miami following cheating allegations. Kylie then spent the holidays without him by taking a sisters’ trip with Kendall to Aspen, Colo.
The mother of two gave a brief update on her co-parenting relationship with Scott in October 2023, telling WSJ. Magazine, “It’s going.”
“I think we’re doing the best job that we can do,” she added.
Timothée Chalamet
Kylie and Timothée Chalamet were first linked in April 2023 after her luxury Range Rover was photographed in the “Dune” star’s driveway.
“It’s been really fun for her because it feels a lot different than her past relationships,” an insider told “Entertainment Tonight” at the time amid the romance speculation.
“It’s new and exciting for Kylie, and she’s having a lot of fun.”
The actor and the Khy founder went public with their romance in September 2023 at Beyoncé’s Renaissance World Tour concert, where they cozied up even passionately made out.
Days later, they were photographed kissing at the US Open.
Kylie proved that she was all in with Chalamet when she accidentally revealed that he was her iPhone background.
In October 2023, fans theorized that the “Wonka” star gave the makeup mogul his Cartier Love Necklace ($4,950), which she seemingly wore as a bracelet in a series of sizzling bikini shots.
Both Kylie and Chalamet have kept their lips sealed about their romance so far.
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