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Bryana Holly (July - November 2013): His first relationship since his split with longtime love Avril Lavigne, Brody began dating the sexy surfer model last summer. Avril Lavigne (February 2010 - January 2012): Despite professing their love for each other with permanent ink, these two were little more than a temporary match made in Hollywood. Nonetheless, their short-lived relationship really Nicole Richie (Fall 2006): Brody and his childhood pal briefly dated after his split from Kristin. Kristin Cavallari (August 2005 - August 2006): The two were the very picture of young love, and later, friends with benefits on "The Hills" (or were they? K-Cav later admitted that her second relationship with Brody was more for show.While we had high hopes for Brody and Bryana, they barely made it past the proverbial honeymoon period before fizzling out. And a Bravril reunion is most definitely not in the cards, as Avril quickly moved on and married Nickelback frontman Chad Kroeger. Re-watch the "Hills: LIVE After Show" moment when Brody announced his split with Jayde: you can't blame him for wanting to live out every young man's pre-teen dreams. The pair reportedly locked lips at a New Year's party, which Brody later denied -- despite the photographic evidence. , which aired Tuesday night on MTV, Brody Jenner and Kristin Cavallari have an emotional goodbye. Cavallari was seen energetically jumping out of the car and running back to Jenner.The pair — who have dated on and off since high school — seemed to be splitting for good. But then cameras panned out to reveal their tears were taped on a movie studio lot. Jenner — who is currently dating Avril Lavigne — played coy on the after show, "The thing is, as you saw on the end — what’s real and what's fake, you don’t know.

"I feel like everyone feels: sad but at the same time very happy.

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

2005: The Prince of Malibu Assumes the Throne Jenner, the youngest son of Caitlyn Jenner and Linda Thompson, broke out a little over a decade ago when he starred in the short-lived reality series The Princes of Malibu.

The show costarred his older brother Brandon Jenner, his best friend Spencer Pratt and his former stepdad, David Foster.

2005: Brody and Kristin Cavallari Sitting in a Tree Jenner started dating Laguna Beach alum Kristin Cavallari in 2005.

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