The duo reportedly started dating after they met at the premiere of Breaking Dawn: Part 1 in November 2011. After the Kylie Cosmetics founder called him her "rumor [sic] boyfriend on Twitter," sources confirmed to Us Weekly that they were a couple.
The "Bored in the House" rapper hosted her 17th birthday party in August 2014. A few days after the gig, he called off his engagement to his baby mama Blac Chyna.
Jenner and Tyga then sparked dating rumors in February 2015, but the musical artist dismissed the speculations and said he was not dating her nor had he left his family to be with her.
But they renewed the rumors six months later when he gifted Jenner a $320,000 Ferarri for her 18th birthday and got a special tattoo dedicated to her. Their relationship was on and off in the months thereafter until they called it quits for good in April 2017.
"There was no crazy fight, we just decided … Well, I decided that I'm really young," Jenner revealed in an episode of Life of Kylie. "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."
Following her romance with Tyga, multiple sources revealed that Jenner moved on with Travis Scott. The pair were first spotted holding hands at the 2017 Coachella Festival before they went on more public dates.
Their love bloomed, with rumors about Jenner's pregnancy dominating the internet that the same year. The then-20-year-old never addressed the speculation and only confirmed it when she gave birth to their daughter, Stormi Webster.
The couple had an on-again, off-again relationship and called it quits for the first time in October 2019. Still, they found their way back to each other by the summer of 2021.
By August 2021, sources confirmed they were expecting another baby, whom they welcomed on February 2, 2022, before splitting for good.
Jenner and Drake sparked romance rumors in November 2019 when they were spotted getting cozy at the rapper's 33rd birthday party.
After the appearance, sources claimed they had "mutual feelings for each other," though reports dismissed it and said Jenner was not interested in a serious relationship with the "God's Plan" rapper.
The romance between Jenner and Timothée Chalamet started in April 2023 when the pair were spotted hanging out in public several times, including at the Paris Fashion Week.
"[They] hang out every week," a source told People. "It's not serious. Kylie is having fun. After years of back and forth with Travis [Scott], she just wants to date without any pressure."