2006: Brody Dates Childhood Pal Nicole Richie After his split from Cavallari, Jenner briefly dated his childhood pal Nicole Richie, who he's known since he was 2, in 2006.
"They pretended that him and Jayde [Nicole] broke up and I was dating Brody, and Jayde and I got into a huge fight because she saw us in a club," Cavallari told Bethenny Frankel in 2013. They were together the entire time." (He and Playboy Playmate Nicole dated for about a year until late 2009.) 2009: The Year of the Bromance After skyrocketing to fame, Jenner starred in his own reality series, Bromance, which he executive-produced from 2008 to 2009.Does he kind of understand your You Tube fame now, after competing alongside a bunch of other digital influencers?He has been right next to my side — both of my parents have — since I started You Tube.We're not opposed to having somebody else join in on our sexcapades." While Jenner was serious about his romance with Carter, his family members weren't too sure it would last.Stepsister Kim Kardashian famously denied Brody a plus-one to her lavish wedding to Kanye West, resulting in some family drama."It was mutual, but Brody really broke up with her," a pal told Us Weekly at the time of the split.Jenner, who was 26 at the time, told Lavigne that he needed to focus on his own career, and refused to go on Lavigne's tour in Asia.2007: Jenner Joins The Hills as Lauren Conrad's Love Interest In 2007, Jenner joined The Hills as Conrad's swoon-worthy new love interest.The relationship was just for show, though, and all parties have since denied any romantic involvement.2014: Jenner Starts Dating Kaitlynn Carter He finally found his match!Jenner started dating the pretty blonde model two years ago.