Keeping up with Kylie Jenner! The reality star has had a busy love life since entering the spotlight at a young age, thanks to her relationships with Travis Scott, Tyga, Jaden Smith and more celebrities.
Before venturing into long-term romances with the rappers, Jenner had a serious relationship with Ramsey IV as a teenager. She briefly dated Cody Simpson before moving on with Smith and being linked to Lil Twist.
The Keeping Up With the Kardashians alum made headlines as she and Tyga sparked romance rumors after meeting in 2011. However, they held off on becoming Instagram official until she turned 18 in 2015. Their on-again, off-again courtship — during which she got cozy with PartyNextDoor — ended in 2017.
She gushed about her “first real, mature relationship” in an October 2016 interview with Complex magazine. “The first year we started hanging out, everyone around him told him not to be with me. I still get comments like, ‘Don’t be with him.’ But we’re not doing it for the public — we love each other,” she explained at the time. “We need to be together at all times. We never get mad at each other, we just figure things out.”
Jenner quickly moved on with Scott. Us Weekly confirmed in September 2017 that the couple were expecting their first child together. The Kylie Cosmetics CEO kept her pregnancy under wraps until after daughter Stormi arrived in February 2018.
She and the Grammy nominee split in October 2019 after more than two years together. Prior to the breakup, Jenner raved about her connection with Scott. “We think the same and we have the same goals and passions in life,” she told Playboy in September 2019. “Besides the fact that we have good chemistry, we have a lot of fun together. You’re my best friend. Through all the ups and downs that every relationship has, we evolve together through them and keep getting stronger.”
Jenner emphasized the pair’s concern for their baby girl after calling it quits. “Travis and i are on great terms and our main focus right now is Stormi,” she tweeted. “Our friendship and our daughter is priority.”
Multiple sources confirmed to Us in August 2021 that Jenner was pregnant with her second child. She and Scott welcomed their son in February 2022, but the twosome didn’t reveal the little one’s name right away. After initially announcing their baby boy was named Wolf, Jenner clarified via social media in March 2022 that the moniker didn’t stick.
Nearly one year later, the Hulu personality shared the first glimpse of baby No. 2’s face — and revealed his name is Aire. The January 2023 announcement came weeks after Us broke the news that Jenner and Scott had called it quits once more.
Following their breakup — which occurred in late 2022 — a source exclusively told Us in April 2023 that close friends of Jenner thought she and Scott would “find their way back to each other again.”
Later that month, however, the Kardashians star was linked to Timothée Chalamet. The pair weren’t “serious” but had hung out “a couple of times,” per an insider.
“Things are very new so it’s hard to tell, but so far [Kylie] likes what she sees,” the source told Us, noting that Jenner was “open to seeing where things go” with the Oscar nominee.
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Scroll to revisit Jenner’s dating history through the years: