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10 Guys Kylie Jenner Has Dated

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Kylie Jenner’s love life was already a tabloid fixture years before she turned it into a business.

Long before “Kylie Cosmetics” became a household name, the youngest Jenner sister was already generating headlines for who she was seen with, not what she was selling. From a teenage romance with an Australian pop singer to the on-again, off-again saga with rapper Tyga that dominated entertainment coverage for years, Kylie’s relationships have tracked almost step for step with her rise to fame. Here’s a rundown of the men who’ve actually made her dating history, separated from the rumor mill that surrounds her.

• Kylie and Jaden Smith were photographed sharing a kiss at Kim Kardashian and Kanye West’s Florence wedding in May 2014, months after the pair had started attending public events together.
• Tyga publicly denied a romance in a September 2014 tweet insisting they were “all just friends,” then went fully public in August 2015 — after Kylie turned 18 — with a $320,000 Ferrari gift and a tattoo dedicated to her.
• Kylie starred in PartyNextDoor’s June 2016 music video for “Come and See Me,” which ends with the two kissing in the rain, before she and Tyga reconciled.

The Teenage Years: Cody Simpson and the First Headlines

Kylie’s dating life technically kicks off in late 2011, when she met Australian singer Cody Simpson at the premiere of The Twilight Saga: Breaking Dawn – Part 1. The two were barely teenagers, and Simpson didn’t do much to protect Kylie’s privacy — he joked about the connection during an appearance on “Hello Ross.” Kylie herself shut it down in 2012, telling the world flatly that they were “just good friends,” which is about as normal a teenage denial as it gets.

Jaden Smith and the Florence Kiss

By 2013, Kylie was closely linked to Jaden Smith, son of Will Smith, and the two were regularly spotted together at public events. The relationship reached its most photographed moment at Kim Kardashian and Kanye West’s wedding in Florence in May 2014, where paparazzi caught the pair kissing — arguably the first time Kylie’s personal life generated the kind of viral attention that would define the rest of the decade for her. Around the same stretch, rumor mills also connected her to Lil Twist and, briefly, to Justin Bieber, though neither ever moved past speculation.

Tyga: The Relationship That Defined Her Early Twenties

No name is more tied to Kylie’s dating history than Tyga, born Michael Ray Stevenson. The pairing started drawing attention in late 2014, and the controversy was immediate — Kylie was still a minor, and the optics were rough enough that Tyga felt compelled to address it directly online.

“We are all just friends,” Tyga tweeted in September 2014, trying to tamp down the age-gap backlash before the relationship had even gone public.

That denial didn’t hold. Once Kylie turned 18 in August 2015, the relationship became official in dramatic fashion — Tyga gifted her a $320,000 Ferrari and got a tattoo in her honor, moves that turned a rumored fling into one of the most heavily tracked celebrity romances of the mid-2010s, on par with the kind of scrutiny other Hollywood relationship histories tend to draw once they go public.

The PartyNextDoor Interlude

A temporary split with Tyga in mid-2016 opened the door for new speculation, this time involving Canadian OVO Sound artist PartyNextDoor, real name Jahron Brathwaite. Kylie appeared in his June 2016 video for “Come and See Me,” which closes on the two of them kissing in the rain — about as unambiguous a signal as a music video can send. When pressed on the rumors later that year, Kylie downplayed it as a fun connection rather than a full-blown relationship, and she and Tyga wound up back together not long after.

Kylie’s romantic timeline has always moved fast and in public, the kind of cycle that keeps fans speculating the same way they do over who a celebrity might date next long before anything is confirmed. With Tyga back in the picture by the fall of 2016, the PartyNextDoor chapter looked less like a new relationship and more like a footnote in a much longer on-and-off story.