Kylie Jenner’s Romantic History: From Tyga To 2 Babies With Travis Scott & More

• Kylie Jenner has been in an in on-again, off-again relationship with Travis Scott since 2017 — however, they reportedly split in Jan. 2023 again
• Kylie and Travis share two children: Stormi, 4, and a son, born in Feb. 2022
• Before linking up with Travis, she was in a relationship with rapper Tyga

Even though she is the youngest of the Kardashian-Jenner clan, Kylie Jenner has seriously made a name for herself. Not only is the 23-year-old an incredibly successful and savvy business woman, she’s a devoted mom and total fashion icon. But one part of Kylie’s life that her fans have always been fascinated by has been her dating history!

Ever since Kylie came into her own on Keeping Up With The Kardashians, the young starlet has captivated audiences for well over a decade. Not only has she grown up right in front of fans’ eyes, she’s also dated in the limelight. Now, we’re taking a walk down memory lane with a look back at Kylie’s dating history!

Cody Simpson

Cody Simpson was Kylie’s first brush with her personal life going very public outside of KUWTK. The two, who were both 14 years old at the time, seemingly started dating after officially meeting at the premiere of Breaking Dawn: Part 1 in November 2011. Cody and Kylie had a cute, flirty moment when the future Kylie Cosmetics founder interviewed him at the premiere, calling the singer her “rumor boyfriend on Twitter.”

While rumors circulated that the two were an item, Us Weekly seemingly confirmed that the two were dating. “They are a couple,” a source shared with the outlet at the time. “They are so cute together.” The innocent romance, however, quietly fizzled out after a few months. Cody has since been in a high-profile relationship with Miley Cyrus, and was recently spotted cuddling up with a mystery woman!

Jaden Smith

Kylie has always had a strong friendship with Jaden Smith, but not many fans of the young stars may know that they were romantically linked in 2013. Kylie took Jaden as her date to big sister Kim Kardashian‘s wedding to Kanye West in 2014, months after the two seemingly ended the flirty part of their relationship. The pair’s young love was kept completely on the DL when they were together. But it seemed by the time Kylie got serious with Tyga, Kylie’s relationship with Jaden remained friendly and supportive. Jaden was seen recently at Kylie’s sister, Kendall‘s, 25th birthday bash.

Lil’ Twist

Kylie and Lil Twist had a rumored romance in 2013, after things went from flirty to friendly with Kylie and Jaden. While this potential romance wasn’t as widely known, it appears that the two went on just a few dates in 2013. Even after things seemingly fizzled out, Kylie and Lil Twist kept things flirty on Twitter. But their relationship never amounted to anything serious.

Tyga

Kylie’s first major high-profile relationship came during her romance with Tyga. The rapper and mogul met at Kylie’s sweet sixteen. It wasn’t until years later when Kylie and Tyga officially started dating in August 2015 — around the time of Kylie’s 18th birthday. The two had an on-again, off-again relationship for roughly two years before officially calling it quits in April 2017. Although rumors have swirled about potential reunions between the two, Kylie has continued to deny any inkling of a romantic connection.

In fact, following a report that the two met-up at a recording studio, Kylie took to Twitter to shut down any further speculation. “The internet makes everything 100 times more dramatic than what it really is. There was no ‘2am date with Tyga’. You see me drop two of my friends off at a studio that he happened to be at,” she tweeted on October 3, 2019.

Travis Scott

April 2017 is when Kylie and Travis Scott‘s love story began. The two were spotted at Coachella at the time and things quickly heated up between the two. Less than one year after the couple’s romance started, Kylie and Travis became parents to their first child, Stormi Webster, on February 1, 2018! Throughout their two-year romance, the couple waded through rumors about a potential engagement. But In January 2019, Travis seemingly alluded to a possible proposal!

“It got to a point where I was like, ‘I need [Kylie] with me to operate. She’s that one,’” he shared with our sister publication Rolling Stone. “We’ll get married soon. I just gotta sturdy up — I gotta propose in a fire way,” he said at the time. Months after his profile with the outlet, those romantic plans came to a shocking halt when Kylie and Travis broke up at the end of September 2019.

But following their split, fans often wondered if the two would get back together. Rumors about a potential romance between Kylie and rapper Drake were even thwarted due to the mogul’s still very close relationship with Travis. A source close to Kylie and Travis revealed EXCLUSIVELY to HollywoodLife that the former couple was trying to keep their relationship status “under wraps”, but a new report on Aug. 20, 2021 revealed that Kylie and Travis are expecting another baby together, so that may be hard to do moving forward. They welcomed their second child in Feb. 2022, and initially named him Wolf Webster — before ultimately deciding the name didn’t suit him (the new name has yet to be confirmed).

As of Jan. 2023, it was reported that the couple split once again. “Kylie and Travis are off again, they were supposed to spend the holidays together, but she went to Aspen to be with her family and friends up there,”  a source told Us Weekly. “This has happened so many times before, they’re known to be on again off again, but always remain friends and great coparents.”

Click to Subscribe to Get Our Free HollywoodLife Daily Newsletter to get the hottest celeb news.