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"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.

Hills hunk Brody Jenner and his girlfriend, Kaitlynn Carter, announced on Friday, May 6, that they're engaged after two years of dating.

Here, Us Weekly takes a look back at the 32-year-old star's journey from party boy to future husband.

The now-married mom of three has since described the year-and-a-half romance as her "first mature relationship." They split in 2006.

so sure, depending on what kind of advice you want.” Of course, whether the designer’s relationship with Jenner, 32, ever went beyond the friend zone – and if it was scripted– remains contentious for both celebrities.

“When I did television, scandal was always around me,” she tells for the magazine’s October issue, on newsstands Sept. “And I think one of the best things [about that] for me is that your life becomes more big-picture. It toughened me up, which is good.” in 2006, when Conrad accused Montag of spreading fake rumors about her.

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.

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