Jenner's first reported public romance was with Australian pop singer Simpson. The pair seemingly met for the first time when Jenner was conducting interviews for "On Air with Ryan Seacrest" at the 18 Nov., 2011, premiere of the "Breaking Dawn: Part 1." Rumours had already been swirling that the pair were an item, so flirty banter broke out between the pair almost instantly. "You're my rumoured boyfriend on Twitter," she said to Simpson. "Nice to finally meet you." Ten days later, it was reported the pair were dating, with a source telling Us Weekly at the time, "Yes, they went on a date, and have been inseparable since." Pictures of the pair PDA-ing at an event also circulated online.
As relationships go when you're barely 15, theirs was short-lived, and it's unknown exactly when Jenner and Simpson stopped hanging out.
Jenner denies there was ever a romantic connection between them. "Cody and I are just good friends. That's it," she told Seventeen Magazine in 2012 (via Us Weekly). "We can say that as much as we want and people will still listen to gossip."
Meanwhile, Simpson seemingly didn't mind fanning the flames of the rumour mill. He joked about his relationship with Jenner in a 2014 interview on E!'s "Hello Ross" (via Seventeen), saying, "No, the whole K-O-D-Y thing didn't really work for me." Later, in October 2019, he told "The Kyle & Jackie O Show" that his new music was influenced by his previous celebrity relationships, saying, "I'm writing about the sh*t relationships I've had with the industry, the people in it, women and friends. All that stuff."