Kylie Jenner has had her fair share of high-profile relationships while growing up in the public eye.
Jenner had a few flings in her younger years, but the internet nearly lost it when she entered her first long-term relationship with Tyga, who is seven years older than her. Rumors swirled that they began dating when Jenner was only 17; however, they have both denied those claims.
After dating Tyga on and off for more than three years, the two called it quits. In a 2017 episode of her E! reality show Life of Kylie, Jenner spoke about the importance of enjoying her youth. “Well, I decided that I'm really young,” she said. “I don't want to look back five years from now and feel like [Tyga] took something from me when he's really not that type of person."
Jenner then made headlines once again when she was spotted getting flirty with Travis Scott in April 2017, days after her split from Tyga. The two hit the ground running during the first year of their relationship; they got matching tattoos and welcomed their first child together, Stormi Webster, in February 2018. After a brief split, they welcomed their second child, Aire Webster, in February 2022. Less than a year after the little one’s arrival, the duo called it quits.
For more than a decade, Jenner’s dating life has been giving people something to talk about. More recently, she has been rumored to be dating Timothée Chalamet. At the moment, neither of them has confirmed or denied the reports. So in the meantime, here’s a full look back at Kylie Jenner’s high-profile, and some rumored, relationships.
Cody Simpson talks dating Kylie Jenner: "The whole K-O-D-Y thing didn't really work for me"
When: 2011
In 2011, Jenner and Simpson sparked dating rumors. At the time, neither of the two acknowledged the relationship. Three years later, after old photos of them together surfaced on Twitter, Simpson addressed their reported union.
"The whole K-O-D-Y thing didn't really work out for me," the singer joked on E!'s Hello Ross about his time with Jenner.
When: 2013
While Jenner and Smith never publicly acknowledged their relationship, there were several signs that pointed toward being more than friends. During an interview with Wonderland in April 2013, Smith gushed about Jenner surprising him in London.
"I was in L.A. We were all hanging out,” Smith recalled. “Then I went to New York and she came too, and then she came here [to London] and surprised me. So that's pretty baller."
He added, "She's one of my best friends. It's pretty awesome."
A few months later for Smith’s 15th birthday, Jenner posted a sweet tribute dedicated to her “best friend.” In her caption, Jenner confessed she couldn’t “remember exactly when we met [but] I couldn’t be more grateful that we did.”
She continued, "You understand me like not many do, and you always know the right time to make me laugh."
The pair never confirmed they dated, but they were spotted leaving a movie theater holding hands in 2013.
When: 2014
As fans of Keeping Up With the Kardashians might recall, Jenner first met Tyga at her sister Kendall’s 16th birthday party in November 2011. It wasn’t until three years later that their paths would cross again.
At the time, Tyga threw a 17th birthday party at his home for Jenner. Days later, Tyga called off his engagement to his fiancée Blac Chyna, with whom he shares a son. Tyga then appeared on the Breakfast Club and shot down any rumors of leaving Chyna for the underage reality star.
"No, I'm not dating Kylie," he said in February 2015. "I wanna be clear to everybody. I didn't leave my family to be with Kylie. That's ridiculous."
Six months later, however, Tyga bought Jenner a Ferrari for her 18th birthday, just months after getting her name tattooed on his arm. Shortly after, Jenner appeared in Tyga’s video for his song “Stimulated,” which was rumored to be about her. And while things appeared to be going well for the two of them, they hit a bump in the road and called it quits in May 2016. It wouldn’t take long before they found their way back to each other a few months later.
Jenner and Tyga ultimately called it quits for good in April 2017. In an episode of Life of Kylie, Jenner spoke candidly about the breakup with her first long-term boyfriend. "There was absolutely not one thing wrong with me and T,” she said. "There was no crazy fight. We just decided… Well, I decided that I'm really young. I don't want to look back five years from now and feel like he took something from me when he's really not that type of person."
As for Tyga, he echoed a similar sentiment about the amicable breakup during an interview with Big Boy TV in December 2020. “It got to the point where it was like, ‘I respect you. You respect me,’” he said. “I think it’s a mutual thing. This is what needs to happen. When something is so damaged or something is just not right, you can’t fix it in a moment. The only thing is time.”
He also said there’s a possibility that they might rekindle things later on in life. “Maybe later on in life, maybe we might come back,” Tyga said. “She’s young. When you’re young, you’re going to make mistakes. All of those mistakes are going to be in the public eye so that puts a lot of strain on the relationship.”
Kylie Jenner clears up that PARTYNEXTDOOR relationship: "It never really got to that boyfriend-girlfriend stage."
When: 2016
After Jenner appeared in Partynextdoor’s 2016 music video for “Come and See Me,” which featured a steamy kiss at the end, rumors spread that the two were an item. During an interview for Jenner’s Complex cover story that same year, she clarified her relationship with PND. “He asked me to be in the ‘Come and See Me’ video, and that was after Tyga,” Jenner began. “Me and PARTY have a cool relationship. I think he’s so talented, and I love his music. But I wouldn’t say we dated.”
Jenner then added that while she and PND enjoyed each other’s company, “it never really got to that boyfriend-girlfriend stage.” She added, “I was doing what I wanted to do.”
When: 2017
Shortly after Jenner and Tyga split (days later), the reality star and Scott sparked dating rumors after they were spotted holding hands at Coachella in April.
After the music festival, the two were spotted out and about on several occasions. By September 2017, reports surfaced that they were expecting their first child together. At the time, Jenner didn’t address the rumors and stayed out of the public eye. On Feb. 1, 2018, Jenner gave birth to their daughter Stormi Webster and uploaded a tribute to the little one on YouTube to announce her arrival.
The new parents then opened up about their relationship post-birth during a September 2019 interview with Playboy. "A lot of people claim that having a baby can hurt your sex life, but I feel like that's the opposite of our experience," Scott said. One month later, Scott and Jenner called it quits for the first time.
By summer 2021, Jenner and Scott were back on. People reported in August 2021 that the two were expecting yet another child together. She gave birth to their son Aire Webster on Feb. 2, 2022. Less than a year after welcoming him, the two once again called it quits. A source told People that Jenner was solely focused on their kids.
"Kylie is very focused on her kids and her business,” the insider said. “She is not a big partier. Travis is the opposite. He likes to party. They definitely have different focuses. They always did."
When: October 2019
During Jenner’s break from Scott in October 2019, rumors surfaced that she was spending time with Drake. A source told Us Weekly that their relationship had briefly gone from platonic to romantic.
“Kylie and Drake’s friendship did take a romantic turn recently,” the insider told the outlet. “At his Halloween party, they were affectionate and clearly there together. They’ve been seeing each other romantically. He also showed up to Kendall [Jenner]’s birthday.”
This isn’t the first time that Drake has been rumored to have had relations with a member of the Kardashian-Jenner clan. In September 2018, Kanye West, who was married to Kim Kardashian at the time, believed that Drake was referring to his wife in his song “In My Feelings.”
“People making rumors or thinking you fuck my wife and you’re not saying nothing… That don’t sit well with my spirit,” West said in an Instagram video. “You know, if I had a girlfriend from Chicago, her name was Renita, and you was married to Rihanna, I wouldn’t make no song called ‘Riri.’ So when you’re like, ‘I don’t know where it came,’ you too smart for that, bro.”
Earlier this month, Drake released a song that samples an audio clip of Kardashian discussing her divorce from West. The cover art featured a woman who also looks similar to the SKIMS mogul.
When: January 2023
Gossip account Deux Moi shared a screenshot of a conversation with someone who said that Jenner and Chalamet are an item. The insider said that the two have been involved since January.
The unidentified messenger claimed they learned the information from a “girl who was on Euphoria.” The rumor hasn’t been confirmed by either Jenner or Chalamet.
