Kylie Jenner’s Dating History: From Tyga to Travis Scott

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

The reality star’s first major romance began when she was only a teenager, with rapper Tyga, who is seven years her senior. The rapper showered her with lavish gifts during their on-again-off-again relationship, including a Ferrari and a promise ring. But after almost three years together, they called it quits 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 first-time parents to daughter Stormi Webster. After taking some time apart from late 2019 until mid-2021, they welcomed a baby boy in February 2022.

Jenner and Scott called it quits again less than a year after welcoming their son.

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

The young parents posed for the cover of Playboy in 2019, and Jenner didn’t hold back when discussing her sexuality after having a baby: “You can be sexy and still be a badass mom.”

In the story, Jenner told the “goosebumps” 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 you’re not a good mother.”

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

Cody Simpson

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

Years later, when photos of the teens embracing resurfaced, the “On My Mind” singer spoke out about why things didn’t work out with the reality star.

“The whole K-O-D-Y thing didn’t really work out for me,” he joked on E!’s Hello Ross about the short-lived romance.

Jaden Smith

Jenner never officially revealed that she was in a relationship with Jaden Smith, despite signs pointing to the two being more than friends.

In April 2013, Smith, then 14, told Wonderland Magazine: “I was in L.A., we were all hanging out. 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.”

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.” Though she didn’t remember the moment they met, she added, “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.”

Tyga

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 on Keeping Up With The Kardashians.

However, it wasn’t until three years later that they were seen together again. The rapper, who was engaged to Blac Chyna at the time, hosted Jenner’s 17th birthday party at his home in August 2014. Days later, Tyga called off his engagement to Chyna, with whom he shares one child.

In February 2015, the “Rack City” rapper made an appearance on The Breakfast Club and shut down rumors of their relationship. “No, I’m not dating Kylie,” he said. “I wanna be clear to everybody, I didn’t leave my family to be with Kylie. That’s ridiculous.”

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

Despite things going well between the pair for some time, the couple called it quits in May 2016. But just a few months later, they were back on again. In an October/November 2016 cover story for Complex, the makeup mogul spoke about her temporary split from Tyga.

“I just needed to see what it was like not being with him. We realized that wasn’t what we wanted,” she told Complex.

By April 2017, their relationship came to an end for good. In an August episode of Life of Kylie, Jenner opened up about her breakup with Tyga for the first time.

“There was absolutely not one thing wrong with me and T. He and I will always, always have a bond,” 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 in five years from now and feel like he took something from me when he’s really not that type of person.”

Travis Scott

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 spotted out together regularly, and they even got matching tattoos only a few months into their rumored relationship.

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 Feb. 4, 2018, the couple announced that they had welcomed their daughter, Stormi Webster, on Feb. 1. After staying private for the first few months of Stormi’s life, Jenner and Scott made their post-baby return to the red carpet at the 2018 Met Gala.

The couple opened up about their relationship (and sex life) in Playboy‘s “Pleasure Issue” in September 2019. In the interview, they revealed the arrival of their daughter hadn’t gotten in the way of them connecting on a physical level.

“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,” the “Sicko Mode” rapper said.

By October 2019, however, the couple of over two years had called it quits. Jenner was briefly rumored to have gotten close to Drake during her time apart from Scott, but the parents were together again by summer 2021. In August 2021, PEOPLE confirmed that the on-again couple was expecting baby number two.

Jenner later announced that she had given birth to a son on Feb. 2, 2022. Their son was born just one day after big sister Stormi’s 4th birthday. The pair initially named their newborn Wolf, but later changed his name (and have yet to publicly reveal the new moniker).

Scott and Jenner called it quits for a 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 business. She is not a big partier. Travis is the opposite. He likes to party. They definitely have different focuses. They always did.”

Drake

In 2019, after splitting from Scott, a source told PEOPLE that Jenner had been “spending some time” with Drake.

“They’ve been friends for a long time and Drake is very close to the family,” the source said.

One friend told PEOPLE that the pair had been “flirting and hanging out” since Jenner called it quits with Scott in October. However, other insiders insisted the two were “just friends.” The pair began seeing each other after Jenner attended the rapper’s 33rd birthday party and his Halloween party a few days later, with a source adding that she stayed “super late.”

Source: people.com