Before there were billionaire lip kits or elusive Timothée Chalamet sightings, there was Jaden Smith. Honestly, it’s easy to forget because the Kardashian-Jenner machine moves so fast, but Jaden and Kylie were basically the blueprint for the modern "cool kid" celebrity couple.
They were 14 and 15. Think back to 2013. Jaden was wearing Iron Man suits to the movies and Kylie was still finding her signature look—long before the fillers and the high-glam transformation. To the outside world, they were inseparable. To the tabloids? They were a goldmine. But the actual nature of their bond was always a bit of a moving target.
The "Baller" Era: Best Friends or Secret Lovers?
Jaden Smith on Kylie Jenner has always been a topic he handles with a specific kind of laid-back loyalty. In 2013, Jaden sat down with Wonderland Magazine and gave us one of his most famous quotes about her. He called her "baller."
He told the mag that she surprised him in London, and that she was one of his "best friends." At the time, that was the standard line. They weren't dating; they were just "besties." But if you were on Instagram back then, the photos told a different story. They were constantly seen holding hands, and Kylie was always rocking Jaden’s MSFTSrep gear.
They had this specific vibe. It wasn't just Hollywood; it was Calabasas. They grew up in the same gated neighborhood. Their families were already intertwined. When your parents are Will Smith and Kris Jenner, the "normal" rules of teenage friendship don't really apply. You’re navigating fame together.
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The Kimye Wedding Incident
One of the biggest "gotcha" moments happened in 2014. It was May. Kim Kardashian and Kanye West were getting married in Florence. It was the event of the century for that family.
Guess who was there? Jaden.
Reports from the wedding reception suggested the two were seen making out. It was the first real "confirmation" for many fans that this wasn't just a platonic friendship. Even though they never did the big "Instagram official" launch like people do now, the industry knew.
Why the Relationship Actually Matters Now
You might wonder why we're still talking about a teenage romance from over a decade ago. It's because that relationship represents the last "innocent" version of Kylie. Shortly after she and Jaden drifted apart, she started her relationship with Tyga. That’s when the "King Kylie" era began. Her look changed. Her brand exploded.
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A lot of fans look back at the Jaden years with a weird kind of nostalgia. It was a time when she was just a girl hanging out with a guy who liked to skate and talk about the universe.
Jaden didn't seem to care about the cameras as much as he cared about the "vibes." He even wore a white Batman suit to Kim’s wedding—or was it the Iron Man suit for a date? He was quirky. She was quiet. It worked.
The Aftermath and Current Status
Do they still talk? Totally.
They didn't have one of those messy, public breakups that end in "unfollowing" and deleted photos. When Jaden’s sister, Willow, or his friends like Harry Hudson are around, Kylie is usually in the mix. They are part of a very specific, very wealthy social circle that doesn't really let outsiders in.
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- They still support each other's brands.
- They've been spotted at the same parties (like Coachella) for years.
- Jaden even stayed close with Jordyn Woods after the Tristan Thompson scandal, which showed he stays out of the family drama.
The Lessons of Young Hollywood Love
The most interesting part of the Jaden Smith and Kylie Jenner story is how it didn't end in a disaster. In a world where celebrity breakups are usually weaponized for reality TV ratings, they just... evolved.
Jaden became a fashion icon and environmental activist. Kylie became a mogul and a mother. They grew up.
If you’re looking for a scandal here, you won't find one. What you'll find is a blueprint for how to handle a childhood connection when both people become some of the most famous humans on the planet. They kept the "baller" energy and left the drama for the screen.
Takeaways for Navigating High-Stakes Friendships:
- Privacy is Power: Notice how they never confirmed the "dating" rumors? It kept the pressure off.
- Family First: Maintaining a good relationship with the siblings (like Jaden and Kendall) keeps the bridge from burning.
- Evolve Together: You don't have to be "together" to be supportive. Supporting a friend's business or music years later proves the bond was real, not just a PR stunt.
Check out Jaden's older music like "Know Why" if you want to hear those early-2010s references to his "soldier" era. It's a time capsule of a very specific moment in pop culture history.