Kylie Jenner and Jaden Smith have been friends for well over a decade, but many people don’t seem to know that these two were once dating. Their romance was short-lived, but considering how inseparable they were from one another at the time, it didn’t seem like either one of them was hiding their romance.
Reports about their relationship first emerged in 2013, the same year Jenner would be seen flying to New York to surprise her ex before jetting off to London together for a brief vacation. Needless to say, the fact that they were always together had already insinuated that there was a romance brewing between the two.
And though neither one of them ever commented on the dating claims, there’s enough evidence to prove that Jenner and Smith were once seeing one another. Besides, the relationship only lasted a few months, so it wasn’t necessarily anything to brag about.
When Did Kylie Jenner Date Jaden Smith?
Before Tyga would share a two-year on-again, off-again relationship with the Kylie Cosmetics CEO, Jenner had been spending a lot of time with Will Smith’s son, who grew up in the same neighborhood as the Kardashians.
It’s unclear how long they’ve been pals, but considering that there are photos of them together that date back to 2011 - at the premiere of Justin Bieber’s Never Say Never concert movie in LA, they’d definitely known each other for a while.
In April 2013, Smith was asked about his friendship with the reality star in an interview with Hello magazine, saying: "She's one of my best friends. I was in LA, we were all hanging out. Then I went to New York and she came too, then she came here and surprised me, so that's pretty baller.”
And it wasn’t long after that when insiders claimed that these two were more than just friends.
"They're dating," a source told Us Weekly in March 2013. "It's new, but they've been friends forever.”
The news came shortly after Jenner and Smith were seen on a lunch date at Caffe Nero in London before the 22-year-old would embark on an international promotional campaign with his dad for their blockbuster flick After Earth.
Smith is also believed to have been the one who introduced Jenner to Jordyn Woods, who had been a family friend to the Smith family since the ‘90s.
The pair instantly formed a friendship and remained close up until February 2019 when Woods was caught up in a cheating scandal with Khloe Kardashian’s on-off boyfriend Tristan Thompson.
By the end of 2013, Jenner and Smith appeared to have called it quits, which seemed evident after photos of Jenner and rapper Tyga had surfaced out and about in Los Angeles together.
By July 2014, the mother-of-one seemed to confirm her relationship with the Faded chart-topper when she posted him on her Instagram page, just one month before celebrating her 17th birthday with her beau.
The former couple shared a three-year on-again, off-again relationship before calling deciding to split for good in March 2017.
A source for Hollywood Life claimed that the romance between Tyga and the cosmetics mogul had run its course, adding that the Keeping Up With the Kardashians star was ready to move on.
“It looks like Kylie HAS finished with Tyga, at least for now anyway,” a source gushed. “She changes her mind like she changes her underwear though and Tyga has a habit of always managing to sneak his way back into her bed somehow.
“Basically Kylie was bored with the relationship, she didn’t feel like it was going anywhere and after 18 plus months Tyga still hadn’t put a ring on it, so, you snooze, you lose.
“Kylie isn’t seeing anyone else, and she doesn’t think he was cheating, but she’s confident she can land herself a hotter, richer boyfriend.”
Well, the source wasn’t lying because the following month, in April 2017, Jenner was introduced to rapper Travis Scott, who she began dating that very same month.
Then, in September 2017, TMZ exclusively revealed that the 23-year-old was expecting her firstborn with the Highest In The Room hitmaker.
She remained out of the spotlight for the majority of her pregnancy and gave birth in February 2018 to a healthy baby girl named Stormi Webster.
As for her friendship with Smith, Kylie has continued to remain on good terms with her ex, who’s still one of her closest pals in Hollywood.
As for her ties with Tyga, while the two have shared many run-ins in Hollywood, sources say they're not on speaking terms anymore.