Kylie Jenner Dating History From Cody Simpson To Timothee Chalamet By 29

Whether single or in a relationship, Kylie continues to captivate fans worldwide—not just for her love life but for her influence as a beauty mogul and pop culture icon. 

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Kylie Jenner Dating History

Kylie Jenner, one of the most influential figures in the beauty and fashion industry, has lived much of her personal life in the public eye. Her dating history has often been the subject of media headlines, with relationships ranging from early flings to long-term romances with fellow celebrities. Here’s a look back at Kylie Jenner’s romantic timeline.

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1. Cody Simpson (2011)

Kylie’s earliest rumored romance was with Australian pop singer Cody Simpson. At the time, both were in their teens, and the relationship was never officially confirmed. They eventually parted ways and remained friendly. 

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2. Jaden Smith (2013)

In 2013, Kylie was linked to actor and rapper Jaden Smith. Their appearances together at events and on social media sparked dating rumors. Although neither publicly confirmed the relationship, their close bond was evident.

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3. Lil Twist (2013–2014)

Kylie was briefly linked to rapper Lil Twist, a close friend of Justin Bieber. This rumored relationship was short-lived and faded without much public detail.

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4. Tyga (2014–2017)

Perhaps one of Kylie’s most controversial relationships was with rapper Tyga. The two met when Kylie was still a minor, sparking public debate when they began dating officially in 2014. Their relationship was marked by public appearances, social media declarations, and occasional drama before ending in early 2017.

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5. Travis Scott (2017–2023)

Kylie’s relationship with rapper Travis Scott became one of her most significant. The couple started dating in 2017 and quickly became inseparable. In 2018, they welcomed their first child, Stormi Webster. They later had a second child, Aire Webster, in 2022. Despite occasional breakups, they maintained a co-parenting relationship after officially splitting in 2023.

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6. Drake (2019 Rumors)

Following her initial split with Travis Scott, Kylie was briefly linked to rapper Drake. Reports suggested the two had been spending time together, but sources claimed it was casual and never turned serious.

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7. Timothée Chalamet (2023–2025?)

In 2023, Kylie surprised fans when she was spotted with Hollywood actor Timothée Chalamet. The relationship was kept relatively private, with only rare public appearances, including their viral PDA at the US Open. However, in 2025, split rumors began circulating after Kylie’s cryptic playlist posts on social media.