Kylie Jenner’s Dating History: From Tyga to Timothée Chalamet

Kylie Jenner has had several high-profile relationships over the years.

The reality star’s first big romance started when she was just a teenager, with rapper Tyga, who is seven years older than her. The rapper showered her with lavish gifts during their relationship, including a Ferrari and a promise ring. But after almost three years of being together, they broke up for the last time in April 2017.

The same month her relationship with Tyga ended, Jenner began dating Travis Scott (born Jacques Bermon Webster II). Less than a year later, they became parents for the first time to daughter Stormi Webster.

The young parents posed for the cover Playboy 2019, and Jenner didn’t hold back when discussing her sexuality after giving birth. “You can be sexy and still be a bad mom,” she said.

In the story, Jenner told the “chilling” rapper, “You remind me that motherhood and sexuality can coexist, and just because you embrace your sexuality doesn’t mean you have loose morals or aren’t a good mother.”

After separating for some time from late 2019 to mid-2021, the couple welcomed a baby boy in February 2022. Jenner and Scott broke up again less than a year after they had son Aire.

“They have divorced several times in the past and this is probably not the end of their relationship,” a source told PEOPLE in January 2023.

Recently, the Kylie Cosmetics founder was linked to actor Timothée Chalamet.

From her early relationships to enjoying parenthood with Scott, here’s a complete look at Kylie Jenner’s relationship history.

Cody Simpson

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In 2011, the youngest member of the Kardashian-Jenner family was rumored to be dating Australian singer Cody Simpson. However, neither Jenner nor Simpson acknowledged the relationship at the time.

Years later, when photos of teenagers hugging Reemerging, the “On My Mind” singer opened up about why things didn’t work out with the reality star.

“The whole KODY thing didn’t really work out for me,” he joked on E! Hello Ross about a short-lived romance.

Jaden Smith

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Jenner has never officially revealed that she is in a relationship with Jaden Smith, despite signs that the two are more than friends.

In April 2013, Smith, then 14, said Wonderland magazine: “I was in LA, we were all hanging out. Then I went to New York and she came too, and then she came here [to London] and he surprised me, so that’s nice.”

He added: “She’s one of my best friends. It’s pretty cool.”

Jenner also had kind words to say about Smith for his 15th birthday in July 2013, posting a photo and caption dedicated to her “best friend.” Although she didn’t remember the moment they met, she added, “I couldn’t be more thankful that we did.”

She continued: “You understand me like no one else and you always know the right time to make me laugh.”

Tyga

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Jenner’s first long-term relationship was with rapper Tyga. The former couple first met in November 2011 at Kendall Jenner’s 16th birthday party, as seen in Keeping up with the Kardashians.

However, they were seen together again only three years later. The rapper, who was engaged to Blac Chyna at the time, hosted Jenner’s 17th birthday party at his home in August 2014. A few days later, Tyga called off his engagement to Chyna, with whom he shares one child.

In February 2015, the “Rack City” rapper appeared on The breakfast club and shut down rumors about their relationship. “No, I’m not dating Kylie,” he said. “I want to be clear to everyone, I didn’t leave my family to be with Kylie. It’s ridiculous.”

However, just six months later, he gave the newly married 18-year-old Jenner a $320,000 Ferrari for her birthday, after getting a tattoo dedicated to her. That same month, she appeared in the music video for his song “Stimulated,” which features lyrics rumored to be about the reality star.

Despite things going well between them for a while, the couple broke up in May 2016. But just a few months later, they were back together again. In the cover for October/November 2016 Complexmakeup mogul has opened up about her temporary breakup with Tyga.

“I just needed to see what it’s like to be when I’m not with him. We realized that’s not what we want,” she told Complex.

By April 2017, their relationship was broken for good. In the August episode Life of KylieJenner spoke for the first time about her breakup with Tyga.

“There was absolutely nothing wrong with me and T. He and I will always, always have a relationship,” she said. “There was no crazy fight, we just decided… Well, I decided I’m really young. I don’t want to look back in five years and feel like he took something from me, and he’s not really that type of person.”

Travis Scott

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The Kylie Cosmetics founder first sparked romance rumors with Travis Scott when they were spotted holding hands at Coachella in 2017. It wasn’t long before the pair were regularly seen together and even got the same tattoos just months into their relationship on which was talked about.

By September 2017, multiple sources confirmed to PEOPLE that Jenner was pregnant with her first child. However, the then 20-year-old never confirmed the rumors and kept fans in the dark for months.

In a YouTube video posted on February 4, 2018, the couple announced that they welcomed their daughter, Stormi Webster, three days early. After keeping private for the first few months of Stormi’s life, Jenner and Scott returned to the red carpet at the 2018 Met Gala following the birth of their child.

The couple opened up about their relationship (and sex life) in Playboy‘Pleasure Issue’ in September 2019. In an interview, they revealed that the arrival of their daughter did not hinder them from connecting on a physical level.

“A lot of people claim that having a kid can hurt your sex life, but I feel like that’s the opposite of our experience,” the “Sicko Mode” rapper said.

By October 2019, however, the couple of more than two years had broken up. Jenner was briefly rumored to have gotten close to Drake during her time away from Scott, but the parents were back together by the summer of 2021. In August 2021, PEOPLE confirmed that the couple was again expecting their second child.

Jenner later announced that she gave birth to a son on February 2, 2022. Their son was born just one day after older sister Stormi’s 4th birthday. The couple initially named their newborn Wolf, but later changed his name and later introduced him as Aire.

Scott and Jenner broke up for the second time less than a year after welcoming their son.

“She spent the holidays in Aspen with her family,” a source told PEOPLE in January 2023. “[But] this is probably not the end of their relationship.”

The insider continued: “Kylie is very focused on her kids and her work. She’s not a big party girl. Travis is the opposite. He’s fun-loving. They definitely have different focuses. They always have.”

Drake

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In 2019, after her split from Scott, a source told PEOPLE that Jenner was “spending some time” with Drake.

They have been friends for a long time and Drake is very close to the family, the source said.

A friend told PEOPLE that the couple has been “flirting and hanging out” since Jenner broke up with Scott in October. However, other insiders insisted that the two are “just friends.”

The pair began seeing each other after Jenner attended the rapper’s 33rd birthday bash and his Halloween party a few days later, with the source adding that she stayed out “super late.”

Timothée Chalamet

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In April 2023, a source close to Jenner told PEOPLE that Jenner and Timothée Chalamet were “hanging out and getting to know each other.”

TMZ previously shared photos of Jenner’s Range Rover in Chalamet’s driveway. The pair were also spotted interacting during Paris Fashion Week in January.

“[They] hanging out every week,” Jenner’s source informed PEOPLE. “It’s not serious. Kylie is having fun. After years with Travis [Scott]she just wants to date without any pressure.”

The insider added that the reality star’s family is “happy and supportive of Kylie’s relationship.”

In May 2023, a source close to the makeup artist told PEOPLE that “Kylie enjoys going out, but her main focus is being a mom.” They added that her relationship with Chalamet was “frivolous”.

Two months later, Scott seemingly rejected it Wonka star in his song “Meltdown.” Despite this, the couple attended a Beyoncé concert in September, where they kissed while enjoying the performance.

In January 2024, a source close to the couple told PEOPLE that “things have been easy and fun” between Jenner and Chalamet, noting that “Timothée reminds Kylie that he lives in a very ‘present’ way, and she really likes that about him. ”

The insider said the actor gets along well with Jenner’s famous family, adding: “On Kylie’s side, Kris [Jenner] and Kim [Kardashian] they provide special support and feel there is so much potential.”

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Source: HIS Education