Kylie Jenner has spent her entire life under a microscope. It’s a lot. From the time she was a kid on Keeping Up With The Kardashians to her current status as a makeup mogul, her love life has been public property. But when people talk about a Kylie Jenner ex boyfriend, they usually just think of the big names like Travis Scott or Tyga.
There is actually a lot more to the story than just the rappers.
Honestly, the way people frame her past relationships often misses the mark. It wasn't just a series of random flings. These guys—and the drama that followed them—actually shaped the brand Kylie is today. You've probably seen the headlines, but the reality of how these relationships ended (and why they started) is way more nuanced than a 30-second TikTok clip.
The Travis Scott Era: More Than Just Co-parenting
When you think of a Kylie Jenner ex boyfriend, Travis Scott is likely the first name that pops up. They were the ultimate "it" couple of the late 2010s. It all started at Coachella in 2017. Talk about a whirlwind—Kylie basically joined his tour immediately after meeting him.
They have two kids together, Stormi and Aire. That changes everything.
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Despite the matching butterfly tattoos and the $1.4 million Ferrari "push present," things weren't always perfect. By early 2026, the dust has finally settled on their "on-again, off-again" cycle. According to reports from insiders close to the family, the split wasn't about one big fight. It was basically a lifestyle clash. Travis is a workaholic, always in the studio or on the road. Kylie? She’s a homebody who wants a stable domestic life for her kids.
They still co-parent, obviously. You'll see them at birthday parties, but the romantic spark is long gone. Travis has even been rumored to vent about the situation in his music, notably with those "Willy Wonka" lines in "Meltdown" that fans are convinced were aimed at Kylie’s new partner.
The Tyga Controversy: Why It Still Matters
We have to talk about Tyga. If we're being real, this is the relationship that caused the most "internet meltdowns." They met when she was just 14 at Kendall’s birthday party, but they didn't start "dating" until later.
The age gap was a massive talking point.
Tyga once claimed in an interview with Nicki Minaj on Queen Radio that he was responsible for Kylie’s "codes"—essentially saying he helped her find her style and even helped with the early Kylie Cosmetics colors. Whether that’s true or just ego is up for debate. But for Kylie, Tyga was her first "adult" relationship. It was messy. It involved Ferraris, "promise rings," and a whole lot of public scrutiny that most teenagers never have to deal with.
By the time they split in 2017, the relationship had allegedly "overshadowed" Tyga's music career. He told radio host Big Boy that dating someone in the Kardashian orbit was a double-edged sword. It brings fame, but it also makes people forget you actually have a job.
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The Boyfriends You Forgot About
Before the high-profile rap stars, Kylie had a few other notable names on her list.
- Cody Simpson: This was very early days, circa 2011. They were 14. It was "cute" and innocent, mostly documented through flirty tweets and red carpet interviews.
- Jaden Smith: This one was a bit more serious. They were "best friends" who were spotted making out at Kim and Kanye's wedding in 2014. They’ve stayed friends over the years, which is rare in Calabasas.
- Fai Khadra: People always wonder about Fai. While he’s been linked to Kylie during her "breaks" from Travis, they’ve mostly maintained he’s just a close family friend.
Then there are the rumors. Drake? They spent time together in 2019, but sources told People it was never "serious." PARTYNEXTDOOR? That was a brief 2016 moment following a music video cameo.
Life After the Exes: The Timothée Chalamet Factor
It’s 2026, and the conversation has shifted. For the last three years, Kylie has been tied to actor Timothée Chalamet. This is a total 180 from her previous "type."
Insiders say they are "basically married" at this point.
During the 2026 awards season, Timothée even thanked his "partner" during his acceptance speech for Marty Supreme. This relationship is different because it’s private. No more constant paparazzi setups or messy Instagram stories. It seems Kylie has learned from her past with every Kylie Jenner ex boyfriend that sometimes, less is more when it comes to the public eye.
What This Means for Your Feed
If you're following the Kardashian-Jenner soap opera, here is the takeaway. Kylie’s history with her exes isn't just gossip; it’s a blueprint of how she grew up. She went from being a girl influenced by her boyfriends' styles to a woman who sets the trends herself.
Next Steps for the Superfan:
- Audit the "Kardashian Curse": Look at the careers of her exes post-breakup. Most have actually seen a dip in mainstream visibility.
- Watch the Lyrics: Keep an ear out for Travis Scott’s upcoming tracks; he’s known for dropping "easter eggs" about his personal life.
- Follow the Awards Circuit: Since Kylie and Timothée are becoming more public, watch for their rare red-carpet appearances to see how this "mature" era compares to the Tyga/Travis years.
The reality is, Kylie's past relationships are a closed book, but they wrote the intro to the woman she is now. She’s focused on her kids and a much quieter, more stable kind of love. No more Ferraris on the driveway for the cameras—just a "partner" who shows up.
Key Takeaways on Kylie’s Dating History
| Ex-Boyfriend | Period | Main Vibe |
|---|---|---|
| Tyga | 2014-2017 | High drama, controversial age gap, heavy influence on her early brand. |
| Travis Scott | 2017-2023 | The "Family" era. Two kids, lots of public PDA, but ultimately different goals. |
| Jaden Smith | 2013 | The "Bestie" era. Young love that transitioned into a lifelong friendship. |
| Timothée Chalamet | 2023-Present | The "Mature" era. Private, stable, and deeply intertwined with her daily life. |
Understanding the timeline of a Kylie Jenner ex boyfriend helps explain why she’s so guarded now. She’s been through the ringer. Now, she’s just living.