Jenner and rapper Scott were first linked romantically when they were spotted together at Coachella on 17 April, 2017. A week later, the pair were spotted getting close at an NBA playoff game. By May 2017, Jenner posted a picture of the two amidst a group of friends at the Met Gala, making them Instagram official. The two remained together for the remainder of the year, but kept their relationship mainly under wraps.
On 4 Feb., 2018, Jenner and Scott managed to overshadow the Super Bowl by announcing they welcomed their first child, Stormi Webster, on 1 Feb., 2018. "My beautiful and healthy baby girl arrived February 1st and I just couldn't wait to share this blessing. I've never felt love and happiness like this I could burst!" the beauty mogul shared on Instagram.
After the birth of Stormi, Jenner and Scott's relationship thrived. The two appeared at the Met Gala together in May of 2018 and were featured on the cover of GQ that June. Jenner appeared in Scott's music video for "Stop Trying to Be God," and influenced much of his acclaimed "Astroworld" album, which dropped in August. Jenner often referred to Scott as her husband on social media and even openly discussed the possibility of having another kid in the future. By October 2018, the two grew even more serious by reportedly buying a $13.4 million mansion together.
In October 2019, Jenner and Scott split unexpectedly, with a source telling TMZ that they had been "trying to make the relationship work for a while, but . . . decided to step away." However, when the coronavirus pandemic hit the United States in early 2020, the pair decided to quarantine together to maintain a sense of normalcy for Stormi. Speculation Jenner and Scott had reconciled would rage throughout 2020 and well into 2021, but it wasn't until August 2021 that E! News reported the pair were back together. "They hold hands and are affectionate. They aren't shy about showing their love for another. They support each other and are a constant in each other's lives," a source told the publication.
Not long after their reported reconciliation, rumours of Jenner being pregnant with the pair's second child circulated on social media and in the press. Like her first pregnancy, she kept the matter private, but announced via Instagram that she gave birth to a baby boy, Wolf Webster, on 2 Feb., 2022. However, Jenner would later reveal that she had changed her son's name to Aire.
In January 2023, though, Scott and Jenner reportedly called it quits once again after spending time apart. "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 at the time. "This has happened so many times before, they're known to be on again off again, but always remain friends and great coparents."