Kylie Jenner is not only the youngest of the Kardashian-Jenner siblings, but one of the most private — at least when it comes to her love life. The makeup mogul’s partners have rarely shown up on the family’s reality series, even as her sisters have endured divorces and huge cheating scandals in front of The Kardashians’ cameras. That makes it all the more exciting when rumors start swirling about the possibility of new romance in her life. Let’s take a look at Jenner’s dating history with a timeline of her relationships — both confirmed and rumored.
2011: Kylie Jenner Rumored To Be Dating Cody Simpson
Kylie Jenner’s first brush with public romance rumors came when she was 14 years old and was thought to be dating Australian pop star Cody Simpson, who was also 14. The two were photographed together at the mall, E! News reported, and Jenner called him her “rumor boyfriend” when she and sister Kendall interviewed him on Ryan Seacrest’s radio show. Neither of their representatives ever confirmed the news.
2013: Jaden Smith Confirmed To Be Dating Kylie
In March 2013, the Kylie Cosmetics boss was confirmed to be dating Jaden Smith (per US Weekly). It’s unknown how long the relationship lasted or why it ended, but the couple had been friends for years before they got together, and they remained friends after.
2015: Kylie Jenner And Tyga Confirm Relationship With Extravagant 18th Birthday Gift
Speculation that the youngest KarJenner was dating then-24-year-old Tyga started in 2014, when she was still 17, but momager Kris Jenner insisted her daughter was single, People reported at the time. When her 18th birthday rolled around the next year, however, their relationship was confirmed, with Tyga presenting his girlfriend with a $320,000 Ferrari 482 Italia.
Blac Chyna, who shares a son with Tyga, has accused him of ending their engagement to be with Jenner. She went on to get engaged to Jenner’s brother, Rob Kardashian, with whom she also had a child, before their relationship came to a tumultuous end.
November 2015 - April 2017: Kylie And Tyga Have On-Off Relationship
Meanwhile, the next couple of years was no walk in the park for Jenner and Tyga either. In November 2015, People reported the lip kit queen and Tyga were broken up, after she was conspicuously absent from his birthday festivities. The two reunited a few days later but broke up again for a few days in January 2016 amid rumors that he had cheated. In May, the on-off couple went off again, this time for over a month, before getting back together, per Cosmo. It wasn’t until April 2017 that they called it quits for good.
April 2017: Kylie Starts Dating Travis Scott, Giving Birth To Their Daughter Less Than A Year Later
The same month that she and Tyga split for good, Kylie Jenner started dating another rapper — Travis Scott. After hanging out at Coachella, which was part of Scott’s tour, Jenner chose to hop on the bus and join him for his remaining dates, the couple told GQ. Pregnancy rumors began to spread just months into the relationship, and in September it was confirmed that the 20-year-old was pregnant with her first child. Stormi Webster was born February 1, 2018.
March/October 2019: Travis Scott Cheating Rumors, Increased Fighting Lead Couple To Take A Break
In March 2019 — a little over a year after the birth of their daughter — the Astroworld rapper was hit with cheating allegations that prompted Travis Scott to delete his Instagram account. He vehemently denied the accusations, postponing a concert date in Buffalo, New York, to fly back to Los Angeles and patch things up with the mother of his child. They didn’t break up; however, later that year the couple decided to take a break.
That October, E! News reported that Jenner and her partner weren’t “calling it quits on their relationship, but are taking space apart.” The couple had been fighting, and with Scott reportedly stressed about his new music, they chose to cool things down, with the artist moving back into his house in Beverly Hills.
November 2019: Rumors Spread About A Fling With Drake
They may not have called it quits on their relationship, but that apparently didn’t mean Jenner wasn’t free to pursue other interests. Soon after their cooling off period, the Life of Kylie star reportedly started spending a lot of time with longtime friend of the family, Drake. After she attended his birthday party and Halloween party in October, some insiders said the couple was hanging out “romantically,” while other sources said they’d known each other for a long time and remained “just friends.”
Summer 2021: Kylie Jenner And Travis Scott Are Back On, Preparing To Welcome Their Second Child
Reconciliation rumors between Jenner and the father of her child started as early as March 2020, and sources reported at the time that the couple were quarantining together through the pandemic. It’s unknown when exactly she and Scott officially became an item again, but by summer 2021 they were back on, with Baby No. 2 on the way. Jenner gave birth to a son on February 2, 2022, and after some back and forth about what his name should be, they decided to name him Aire.
January 2023: The Couple Split Again After Spending Holidays Apart
The reunion didn’t last, however, and their breakup was confirmed in January 2023, after they spent the holidays apart. Fans had become suspicious that trouble was afoot after Jenner posted several photos from an end-of-the-year getaway in Aspen sans Scott, and one TikToker pointed out that the rapper had unfollowed all of her friends who were present on the trip.
April 2023: Timothée Chalamet Said To Be Hanging Out With Kylie Jenner
Although Jenner has been known to have on-off relationships, it seems like her last breakup with Scott might just stick, as she’s recently been connected to Academy Award-nominated actor Timothée Chalamet. In April, People reported that the couple were “getting to know each other” after meeting in January at Paris Fashion Week. Page Six also reported that they had dinner in March with her sister, Kendall Jenner, and her rumored beau, Bad Bunny.
Neither half of the rumored couple has commented on the nature of their relationship, but after they were seen in April on a taco date, she seemed to drop a big hint with her Met Gala collaboration. Both of her looks at the big event were created by Chalamet’s longtime friend, Haider Ackermann. Might the two be bonding over their love of fashion? Later in May Page Six reported that Jenner was seen leaving the Wonka star’s house, and at least some of her followers think he’s been hanging out at her place too, possibly in the background of her TikTok videos?
Kylie Jenner and Timothée Chalamet are both pretty private people, so it might be a while before we get any kind of official confirmation or clarification on their situation. However, fans can always keep up with at least part of the reality star’s life, as well as the goings-on of the rest of her famous family members, on The Kardashians, which can be streamed with a Hulu subscription.
