Kylie Jenner has spent nearly her entire life on television, evolving from the youngest sibling on Keeping Up with the Kardashians to a billionaire beauty mogul and global fashion icon. Naturally, the world has been utterly captivated by her personal life. The Kylie Jenner relationships timeline reads like a pop-culture diary, tracking her transition from innocent teenage flings to high-profile hip-hop romances, and finally, to her current era of understated Hollywood glamour.
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Kylie Jenner Relationships
As of May 2026, Kylie’s romantic life is the most stable and private it has ever been. Let’s take a chronological dive through the eras of Kylie’s love life.
Cody Simpson (2011–2012)
Long before the lip kits and red carpets, a 14-year-old Kylie experienced her very first Hollywood romance with Australian pop singer and competitive swimmer Cody Simpson. The young pair met at the premiere of The Twilight Saga: Breaking Dawn – Part 1 and dated for a few months.
- The Legacy: This was a sweet, innocent era of matching bracelets and puppy love. Cody later looked back on the romance fondly, joking that the breakup simply came down to the challenges of being teenagers under the intense glare of public scrutiny.
Jaden Smith (2013)
In 2013, Kylie was frequently spotted with actor and musician Jaden Smith. The two were the ultimate Hollywood “cool kids,” running in the same elite Calabasas social circles. Jaden famously gushed about their special bond in interviews, calling her “one of his best friends.”
- The Turning Point: While they never formally confirmed a serious romantic relationship, the peak of Kylie Jenner and Jaden Smith came in 2014, when they were reportedly spotted sharing a kiss at Kim Kardashian and Kanye West‘s lavish Italian wedding. They have remained close friends to this day.
Tyga (2014–2017)
The “King Kylie” era. This was arguably the most controversial and heavily documented chapter in her dating history. Kylie first met rapper Tyga when he performed at Kendall Jenner’s 16th birthday party in 2011, but the two didn’t start hanging out romantically until late 2014.
- The Flashpoint: Because of their nine-year age gap, the couple faced intense media scrutiny. They finally went public when Kylie turned 18, defined by high-profile matching luxury cars, lavish birthday gifts, and cameos in his music videos. After three years of an intense, on-again, off-again dynamic, Kylie Jenner and Tyga split for good in early 2017 due to simply outgrowing the relationship.
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Kylie Jenner and Travis Scott (2017–2023)
Shortly after her split from Tyga, Kylie headed to Coachella in April 2017, where sparks flew with rapper Travis Scott. What started as a casual festival fling fast-tracked into a deep, six-year love story. Within months, the couple got matching butterfly tattoos, and by February 2018, they welcomed their first child, Stormi Webster, following a highly secretive pregnancy.
The relationship between Kylie Jenner and Travis Scott was a pillar of the hip-hop and beauty worlds. In February 2022, they expanded their family with the birth of their son, Aire Webster. However, the pressure of navigating two massive careers while managing an on-again, off-again dynamic took its toll, and the parents officially called it quits for good in early 2023 to focus on healthy co-parenting.
Kylie Jenner and Timothée Chalamet (2023–Present)
Welcome to Kylie’s current, most sophisticated era yet. In early 2023, Kylie shocked pop-culture fans when she was linked to Oscar-nominated Dune actor Timothée Chalamet. The two initially crossed paths at a Jean Paul Gaultier fashion show in Paris and quietly began seeing each other away from the paparazzi.
They famously “hard launched” their romance in September 2023 at a Beyoncé concert, followed by a highly publicized, affectionate appearance at the Golden Globes.
- Where They Stand Now: As of May 2026, Kylie Jenner and Timothée Chalamet are going stronger than ever, recently celebrating a major milestone of three years together. Just this week, the stable couple made headlines after being spotted on a cozy double date in Los Angeles with Kylie’s sister, Kendall Jenner, and actor Jacob Elordi. Timothée even recently gave a rare, heartfelt shout-out during an award speech, thanking Kylie for being his “foundation.” This era is low-key, deeply supportive, and proving that opposites truly do attract.
CelebLoves Commentary: Kylie Jenner’s journey proves that growth changes your taste. She’s transitioned from the chaotic, flashbulb-heavy romances of her youth to a mature, grounding partnership that protects its peace.
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