The relationship with rapper Tyga (Micheal Ray Stevenson) was the first major scandal of Kylie’s romantic life. He was 25; she was 17. The timeline was murky and controversial. Tyga had previously been engaged to Blac Chyna (who would later have a child with Rob Kardashian, creating a bizarrely incestuous reality TV loop).
For nearly two years (2014–2016), Kylie and Tyga were inseparable. He gifted her a Ferrari on her 18th birthday; she starred in his music video for “Stimulate.” This relationship served as Kylie’s angry transformation. She cut ties with childhood friends, bleached her hair, and leaned into an overtly sexualized aesthetic. The Tyga era birthed “King Kylie”—the tumblr-core, grunge-lite icon that launched a thousand makeup tutorials. kylie jenner hot and sexy exclusive
The Breakup Narrative: The romance imploded due to Tyga’s alleged infidelity and financial instability. In Life of Kylie, she lamented feeling held back. The storyline concluded with a whimper, making way for the seismic shift that was about to hit. The relationship with rapper Tyga (Micheal Ray Stevenson)
Simultaneously, the world watched a will-they-won’t-they dynamic with fellow teen icon Jaden Smith. Their relationship was never formally labeled. One day they were kissing at a concert; the next, they were insisting they were “just best friends.” In Life of Kylie, she later reflected on this period, admitting they had “a little thing” but that their bond was too deep for simple romance. This ambiguity became a Kylie hallmark: the power of the undefined exclusive. It keeps fans guessing and headlines churning. she later reflected on this period
Kylie Jenner’s romantic storylines follow a distinct psychological pattern: