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



Kylie Jenner, known for being part of the Kardashian-Jenner clan and a successful entrepreneur with her Kylie Cosmetics brand, has had quite the dating history. Let’s take a closer look at her relationships over the years in simple terms.


Cody Simpson and Kylie Jenner: 2011

Back in 2011 when Kylie was just 14 years old, she was rumored to be dating Australian singer Cody Simpson. They met at the premiere of “Twilight: Breaking Dawn – Part 1.” Although they didn’t confirm it at the time, Simpson later talked about their breakup.


Jaden Smith and Kylie Jenner: 2013

In 2013, Kylie and Jaden Smith spent time together. They claimed to be “best friends,” but there was that one moment when they were caught kissing. Their romance didn’t last, but they remained friends and were seen together at Justin Bieber and Hailey’s wedding in 2018.


Lil’ Twist and Kylie Jenner: 2014

Rumors circulated in 2014 that Kylie was dating Lil’ Twist, but they kept it hush-hush. There was a Twitter exchange where Twist said, “Acting hard to get…Gets you nowhere,” and Kylie responded with a kiss emoji. Unfortunately, their relationship didn’t go the distance, and the reasons remain unknown.


Tyga and Kylie Jenner: 2015-2017

Kylie’s first long-term relationship was with Tyga, which began in August 2015. They first met in 2011 at Kendall Jenner’s 16th birthday party and crossed paths again in 2014 when Tyga ended his engagement. Despite initial denials, Tyga gave Kylie an extravagant gift for her 18th birthday and got a tattoo in her honor. They had some ups and downs, even breaking up in 2016 before reconciling, but by April 2017, it was over for good.


Travis Scott and Kylie Jenner: 2017-2022

After her split with Tyga, Kylie started a new chapter with rapper Travis Scott. They were seen together at Coachella in 2017, and by February 2018, they welcomed their daughter, Stormi Webster. However, it wasn’t until September 2019 that they publicly confirmed their relationship in Playboy’s “Pleasure Issue.” Unfortunately, they broke up in October 2019 but reunited during the summer of 2021. Their second child arrived in February 2022, but less than a year later, they called it quits due to their differing lifestyles.


Drake and Kylie Jenner: 2019

During a brief break from Travis Scott, rumors circulated that Kylie was close to rapper Drake, although it was never officially confirmed. Many believed they were just friends, as Drake is close to their family, but they were seen together at his 33rd birthday party.


Timothee Chalamet and Kylie Jenner: 2023

After her on-again, off-again relationship with Travis Scott, Kylie decided to keep things less serious with Dune star Timothee Chalamet. They were spotted hanging out in April 2023, getting to know each other. Travis Scott later mentioned their breakup in his song “Meltdown,” confirming her relationship with Timothee Chalamet. In September 2023, both Kylie and Timothee were seen at the US Open Tournament, sharing kisses after the game.

Kylie Jenner’s dating history has been quite the journey, with its share of ups and downs. From Cody Simpson to Timothee Chalamet, she has experienced a variety of relationships, making her personal life as captivating as her business endeavors.