While two of his former "Hills" squeezes have happily settled down for the long haul (Lauren Conrad's engaged and Kristin Cavallari is having another baby with husband Jay Cutler), poor Brody Jenner just can't seem to find The One. According to Us Weekly, the "Keeping Up with the Kardashians" star recently split with his girlfriend, model Bryana Holly, which has us wondering if perhaps the Brodster needs to steer clear of models...and reality stars...and anyone else in Hollywood. Take a look back at his relationship history, and share whether you think it's time for Brody to finally consider looking for a lady who's marriage material.
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. While we had high hopes for Brody and Bryana, they barely made it past the proverbial honeymoon period before fizzling out. First Bruce, and now Brody? Must be something in that Jenner water.
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. And a Bravril reunion is most definitely not in the cards, as Avril quickly moved on and married Nickelback frontman Chad Kroeger.
Jayde Nicole (September 2008 - December 2009): The on-again off-again couple called it quits shortly after "The Hills" Season 5, which was a non-shocker after the Playboy Playmate's shoving match with Kristin Cavallari. Truth? It's a miracle they even lasted that long.
Re-watch the "Hills: LIVE After Show" moment when Brody announced his split with Jayde:
Cora Skinner (January-April 2008): The Brodester was linked to this other Playboy model in early 2008. Okay, we guess you can't blame him for wanting to live out every young man's pre-teen dreams.
Paris Hilton (2008): Questionable. The pair reportedly locked lips at a New Year's party, which Brody later denied -- despite the photographic evidence.
Haylie Duff (Summer 2007): Supposed summer fling. Boring stuff. Now moving on to LC...
Lauren Conrad (October 2006): The two didn't have the lasting power that Brody/K-Cav did -- you can thank Jen Bunney for that. Nonetheless, their short-lived relationship really did happen. LC confirmed it and everything. So there.
Re-watch the "Hills" alternate finale in which Lauren and Brody end up together!
Nicole Richie (Fall 2006): Brody and his childhood pal briefly dated after his split from Kristin. Rebound relationship, 'nuff said.
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.
Re-watch the moment Kristin tried to get back together with Brody...and he politely declined:
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Photos: MTV, Pacific Coast News, JD/Reefshots/Splash News, Zodiac/Splash News, Starsurf/Splash News, Eric Boone/Splash News, HotShots Worldwide/Splash News, Getty Images