Jenner has been linked to a number of Hollywood’s young stars of late, many of whom he has appeared with on television in some capacity. In September 2005, the 23-year-old began dating Laguna Beach mainstay Kristin Cavallari but the couple split after a year-long courtship. Weeks later, the reality star began dating Nicole Richie. After Richie and Jenner split, published reports claimed that Jenner’s wingman/manager, Spencer Pratt, helped engineer a plan for Jenner’s stock to increase because he was “the guy who got Nicole to eat.” Later, Jenner entered a relationship with Laguna Beacher Lauren Conrad. In January 2007, it was reported that Jenner had exchanged sexy text messages with a rehab-bound Lindsay Lohan.