2005: Brody and Kristin Cavallari Sitting in a Tree Jenner started dating Laguna Beach alum Kristin Cavallari in 2005.The now-married mom of three has since described the year-and-a-half romance as her "first mature relationship." They split in 2006.(Caitlyn Jenner’s son also revealed some other, well, um, really graphic details about the first time he performed oral sex, but we will spare you.) PHOTOS: The Hills stars, then and now "I'd have to say [the best sex I’ve ever had is] with my girlfriend, Kaitlynn,” Kim Kardashian’s stepbrother confessed in the tamer portion of the interview.We're not opposed to having somebody else join in on our sexcapades." “It’s funny, because a lot of people are always nervous to bring up that subject,” the extremely open reality star continued about threesomes. I want both of those.” PHOTOS: Celebrity sex confessions Speaking of family, Jenner said he “never really” got the birds-and-the-bees talk, but his mom, Linda Thompson, wished him well. ‘Watch out for girls.’ That's all she said,” he concluded.
"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.honestly, we never talk," Jenner revealed about his former stepmom, who was married to his dad, Caitlyn Jenner."There's just been a lot of family drama that doesn't even involve me."Avril didn't like that," the same insider told Us.2013: The Jenner Brothers Join Keeping Up With the Kardashians Brody, his brother Brandon and Brandon's wife, Leah Jenner, all joined season 8 of E! Brody was spotlighted interacting with his stepsiblings and half siblings, but mostly grappling with his broken relationship with his father and his stepmom at the time, Kris Jenner.alum announced on Friday that he proposed to his girlfriend, Kaitlynn Carter, earlier this week and posted a cute picture of a bikini-clad Carter giving him a sweet smooch."On May 4th 2016 I got engaged to my lover and my best friend @kaitlynn_carter," Jenner wrote.