Kylie Jenner shot to fame as the youngest member of “Keeping Up with the Kardashians,” but her story is so much bigger than reality TV. Born in Los Angeles in 1997, Kylie has gone from quiet teen to headline-grabbing mogul, making waves not just for her famous family but for redefining what it means to be a businesswoman in the age of Instagram.
Who could forget the frenzy when Kylie launched her Lip Kits? They didn’t just sell out – they basically broke the internet, and suddenly every celebrity wanted their own makeup line. Kylie’s savvy turn from TV personality to entrepreneur is the stuff of modern legend. Her success with Kylie Cosmetics, bold fashion collaborations, and headline-making social media moves (like that famous Instagram post that reportedly tanked Snapchat’s market value by over a billion dollars) have put her in a league of her own.
The Real Story of Kylie’s Love Life
While the world watched her grow up on screen, Kylie’s approach to relationships has quietly changed over time. These days, she’s dating actor Timothée Chalamet, after first being spotted together in 2023. The two have kept things mostly under the radar – at least by Kardashian standards – but made waves when they were seen looking cozy at Beyoncé’s Renaissance tour.
Before Timothée, Kylie shared an on-and-off romance with rapper Travis Scott, the father of her two kids, Stormi and Aire. Their relationship, which lasted from 2017 to late 2022, had its ups and downs, but they always seemed to come back to each other for the sake of their family. And before Travis, who could forget her much-gossiped-about romance with Tyga, which started when she was just 17?
Over the years, Kylie’s love life has made plenty of headlines – some real, some pure tabloid fiction. She’s been linked to Jaden Smith (the two insisted they were just friends, but were spotted sharing a kiss at Kim and Kanye’s wedding), and briefly dated Cody Simpson when both were still in the early stages of fame. There was a rumored flirtation with model Fai Khadra while she was on a break from Travis, and, unsurprisingly, whispers about flings with celebs like Drake and Christian Combs that never seemed to go beyond speculation.
In a rare, candid interview with Paper Magazine in 2019, Kylie reflected on her history: “I have so many amazing memories with my exes. I think love is something you should cherish.” It’s a simple sentiment, but it says a lot – especially for someone whose every move gets picked apart online.
What’s interesting about Kylie’s relationships is how they seem to mirror her own growth. Her early years were all about young romances with fellow stars who knew the madness of Hollywood life. As she’s matured and built her empire, she’s been more private, and her relationships have seemed more meaningful, too.
Even during big breakups, Kylie tends to protect her privacy. Unlike some family members who hash out their heartbreaks on camera, she usually takes a break from the spotlight, only returning when she’s ready. It’s a surprisingly low-key approach for one of the most-watched women in the world.
Past Relationships
Timothée Chalamet
Christian Combs
Drake
Stephen Bear
Travis Scott
PartyNextDoor
A$AP Rocky
Stitches (rapper)
InkMonstarr
Tyga
Miles Richie
Justin Bieber
Lil Twist
Jaden Smith
Cody Simpson
Ramsey IV
Now, with Timothée, Kylie seems to be doing things differently. They’re spotted at basketball games or grabbing coffee, just enjoying themselves without the constant glamour parade. She appears more relaxed – more herself. For someone who became a global icon partly by crafting the perfect image, it’s refreshing to see Kylie step back and embrace something a bit more real.