Let’s be real: before there was Timothée Chalamet or the Travis Scott era, there was Kylie Jenner and Tyga.
It was messy. It was all over Snapchat. And honestly, it was probably the most controversial thing to happen to the Kardashian-Jenner family in the mid-2010s. If you were on the internet back then, you remember the "King Kylie" era—the blue hair, the lip kits, and the constant sightings of a Ferrari that may or may not have been leased.
But looking back from 2026, the narrative has shifted quite a bit. People don't just see it as a "fun" celebrity fling anymore. There’s a lot of conversation now about what actually went down when the cameras weren't rolling.
The Timeline That Nobody Can Quite Agree On
The biggest sticking point with Kylie Jenner and Tyga has always been the math.
They officially "met" in November 2011. Kylie was 14. Tyga was 22. He was performing at Kendall Jenner’s 16th birthday party, a moment caught on Keeping Up With The Kardashians. You can literally see them on screen together, but at the time, nobody thought twice about it. Tyga was actually with Blac Chyna back then—they even had a son, King Cairo, in 2012.
By 2014, things got weird.
Kylie was 16 turning 17. Tyga started showing up in her Instagram posts constantly. He hosted her 17th birthday party at his house in August 2014, and just days later, he ended his engagement with Blac Chyna.
Naturally, everyone assumed he left his family for a teenager. Tyga went on The Breakfast Club and swore up and down they weren't dating. He told Charlamagne tha God, "I'm not dating Kylie. I just want to be clear to everybody. I didn't leave my family to be with Kylie."
Kanye West, never one to keep a secret, basically outed them in an interview shortly after, saying Tyga was "smart" to "get in early."
Yikes.
Why the Age Gap Was Such a Huge Deal
It wasn't just about the numbers. It was the power dynamic.
Kylie was still a legal minor for a huge chunk of their early relationship. While her family, specifically Kris Jenner and Khloe Kardashian, defended her by saying she was a "special case" who didn't live a "normal" life, the public wasn't buying it. Khloe once famously said that Kylie wasn't going to prom or having slumber parties, so her dating a 25-year-old was somehow different.
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But was it?
In California, the age of consent is 18. They waited until her 18th birthday in August 2015 to "go public" officially. That’s when the Ferrari arrived—a $320,000 gift parked outside Bootsy Bellows in West Hollywood.
Suddenly, they were everywhere. Mexico, St. Barths, New York Fashion Week. They even did a music video for his song "Stimulated," which had some... let's say uncomfortable lyrics about her age.
The Breakup Cycle
They broke up more times than most people change their oil.
- November 2015: Kylie skipped his 26th birthday. People thought it was over. Two days later, they were at the AMAs together.
- May 2016: This one felt real. Kylie started hanging out with PartyNextDoor. Tyga was spotted in Cannes with a model.
- June 2016: Back together. Tyga posted a photo of her on his bed with the caption "They always come back."
What Finally Killed the Romance?
By April 2017, the fire was out.
Most people assume there was some massive cheating scandal or a blow-out fight. But Kylie eventually opened up on her spinoff show, Life of Kylie, and explained it was more about her realizing she was missing out on her youth.
"There was absolutely not one thing wrong with me and T," she said. She basically realized she didn't want to look back in five years and feel like he "took something" from her.
Around that same time, Tyga's ex, Blac Chyna, had started dating Kylie’s brother, Rob Kardashian. They even had a baby together. This meant Tyga’s son (with Chyna) and Kylie’s niece (Dream Kardashian) were half-siblings.
The family tree was a circle. It was getting too complicated, even for a Kardashian.
The Lasting Impact of Kylie Jenner and Tyga
Believe it or not, Tyga claims he’s the reason Kylie Cosmetics exists.
In a 2018 interview on Queen Radio, he said he "stepped in" and taught her how to appeal to Black culture. He claimed he helped her pick colors and names for the lip kits.
Whether you believe that or not, you can't deny that her "King Kylie" persona was heavily influenced by the hip-hop world she was immersed in while dating him. It was a massive branding shift that turned her from the "quiet sister" into a billionaire mogul.
Moving Forward
If you're looking at the Kylie Jenner and Tyga relationship as a lesson in celebrity culture, there are a few things to keep in mind:
- Watch the "Grooming" Discourse: Modern fans often look back at this relationship through the lens of grooming. It’s a serious conversation that has changed how we view older men dating teenage stars.
- Branding is Everything: The "King Kylie" era proved that who you date can fundamentally change your public image and business trajectory.
- The "Rebound" Success: Kylie met Travis Scott at Coachella just weeks after the final Tyga breakup. Sometimes, the end of a long, messy chapter is exactly what's needed for the next big thing to start.
Ultimately, they seem to be on okay terms now. They’ve been spotted at the same clubs over the years, and there's no major beef. But it remains a weird, fascinating time capsule of 2015 internet culture.
If you want to understand the modern-day Kylie, you have to understand the girl she was when she was with Tyga. It was the era that built her, for better or worse.
To see how much she’s changed, compare her 2015 "Stimulated" video appearance to her more recent, stripped-back brand image. The difference is night and day. It shows a clear shift from being a "prop" in someone else’s career to being the undisputed CEO of her own.
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