Olympian athlete Bruce Jenner and songwriter Linda Thompson welcome their son, Brody. He grows up in the lush L.A. lifestyle, with such childhood friends as Nicole Richie (pictured with Linda and Brody), whose father, singer Lionel Richie, is a longtime friend of Bruce and Linda.
Laguna Beach star Talan Torriero introduces Jenner to his friend and MTV costar Kristin Cavallari (right). The two California beauties begin dating, and Cavallari calls their love her "first mature relationship." Adding to Teen People, "He's good-looking and he makes me laugh for hours." In August 2006, after about a year of dating, they call it quits.
With his songwriting mom, music producer step dad, David Foster, and brother Brandon, Jenner stars on the reality TV series, The Princes of Malibu (left). The Fox show follows the brothers as they live the high life off on their parents' dime. After two episodes air, Fox cancels the series.
Jenner begins dating childhood friend, Nicole Richie (left). Richie's father, Lionel, tells PEOPLE, "I was there when [Brody] was born…they grew up together. To see them together now is like, 'Where are you going with this?' But they're having a wonderful time." By October, Richie and Jenner decide theirs is more friendship than romance. In March, Jenner's scheming pal, Spencer Pratt, tells Details that he planned the relationship so Jenner could "become The Guy Who Got Nicole Richie to Eat. Process that sh--, bro. You'll be, like, a f---ing hero to America."
Jenner, 23, finally hits the big time when he begins ''seeing'' The Hills star – and former Laguna Beach good girl – Lauren Conrad (right). "I don't know what you consider dating, but we're seeing each other, we're having a great time with it," Jenner tells PEOPLE. By November, they seem to have cooled down, although their are they-or-aren't they romance is a major MTV-tabloid plotline (especially when he's urged by Spencer Pratt and Heidi Montag to hook-up with Conrad's childhood friend Jen Bunney, which leads to the demise of his friendship with Pratt).
With The Hills becoming the most-watched program for MTV, questions loom regarding the show's authenticity – specifically the flirting coupledom between Jenner and Conrad. "No matter what the speculation, it is all real," Jenner tells the Canada's eTalk. In 2008, he reveals his new girl, Cora Skinner, to the dismay of Conrad fans. But it seems viewers may see a Brody-Lauren happy ending, when his romance with Skinner fizzles.
Jenner nabs his own MTV spinoff, Bromance, where guys compete in the hopes of joining his playboy entourage. Jenner produces the reality show with best friend Frankie Delgado, but the show is canceled after its first season – and Jenner returns to The Hills.
Jenner is off the market! The Hollywood playboy meets his match in Playboy's 2008 Playmate of the Year, Jayde Nicole. "We're completely smitten for each other," Jenner tells PEOPLE. "I'm loving life." The pair appears on episodes of The Hills in 2009, but parts ways after more than a year together in December 2009.
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