Kylie Jenner’s Complete Dating History List: Hop On The Train



Jenner, famous for being the youngest member of the Kardashian-Jenner clan, is not only a reality TV sensation but also a business mogul with a whopping net worth of $750 million, thanks to her successful venture, Kylie Cosmetics.


Kylie’s Early Dating Days: 2011-2014

Back in 2011, when Kylie was just fourteen, she entered the dating scene. Rumors swirled that she was romantically linked with Australian singer Cody Simpson. Although neither of them confirmed the relationship at the time, years later, Cody Simpson did speak about their past romance, revealing that things didn’t quite work out.

In 2013, Kylie was seen hanging out with Jaden Smith. While they denied dating and claimed to be best friends, they were caught sharing a kiss. Their romance was short-lived, but they remained good friends and even attended Justin Bieber and Hailey’s wedding together in 2018.

Kylie Jenner’s name was also linked with Lil’ Twist in 2014, although they kept their relationship under wraps. Their secretive romance became public when Lil’ Twist tweeted, “Acting hard to get… Gets you nowhere,” and Kylie replied with a kiss emoji. Unfortunately, the reasons behind their breakup remain a mystery.


The Tyga Era: 2015-2017

Kylie’s first long-term relationship began in August 2015 with rapper Tyga. They initially met at Kendall Jenner’s 16th birthday party in 2011 but crossed paths again in 2014 after Tyga ended his engagement with Blac Chyna. Despite rumors suggesting Tyga left Chyna for Kylie, he denied them. However, he gifted Kylie a $320,000 Ferrari for her 18th birthday and even got a tattoo dedicated to her.

Their relationship had its ups and downs, including a brief split in May 2016. But they reconciled a few months later. Ultimately, in April 2017, they called it quits on their long-term romance.


Travis Scott and Kylie’s Rollercoaster Love: 2017-2022

After parting ways with Tyga, Kylie embarked on a new journey with rapper Travis Scott. Their romance became public when they were seen holding hands at Coachella in 2017. By February 2018, Kylie gave birth to their daughter, Stormi Webster.

Although they had been together for a while, the public got a more in-depth look at their relationship in September 2019 when they opened up to Playboy’s “Pleasure Issue” about their dating life. Sadly, they split in October 2019, with Kylie focusing on her daughter.

In the summer of 2021, Kylie and Travis rekindled their romance, welcoming another child in February 2022. Less than a year after their son’s birth, they decided to go their separate ways due to their differing lifestyles.


Drake and Kylie’s Rumored Connection: 2019

During a brief split from Travis Scott, rumors circulated that Kylie was getting close to rapper Drake. Although no concrete sources confirmed their relationship, they were spotted together at Drake’s 33rd birthday party. Many insisted they were just friends, especially considering Drake’s close ties to the Kardashian-Jenner family.


Kylie’s Latest Flame: Timothee Chalamet in 2023

In 2023, after a series of on-and-off moments with Travis Scott, Kylie Jenner found herself in a less serious relationship with Timothee Chalamet, known for his role in “Dune.” The two were first seen hanging out in April 2023, and reports suggest they are getting to know each other better.

Travis Scott dropped a track called “Meltdown” a few months later, seemingly confirming Kylie’s new romance with Timothee Chalamet. The couple made a public appearance at the US Open Tournament in September 2023, where they were even spotted sharing a kiss after the game.



Kylie Jenner’s dating history is a rollercoaster ride of ups and downs, filled with high-profile romances and brief flings. From her early days with Cody Simpson to her recent connection with Timothee Chalamet, Kylie’s love life has certainly been eventful, capturing the attention of fans worldwide.