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. Lauren Conrad (October 2006): The two didn't have the lasting power that Brody/K-Cav did -- you can thank Jen Bunney for that.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. picked up Brody Jenner's call-in talk show, they described him as a "sex connoisseur"—and while we have no way of proving his abilities in that, erm, arena (though he did tell us how to kiss), we [View image]( | [gettyimages.com]( __First Date:__ July 2013 __Love Story:__ Brody's third—yes, third—*Playboy* model.__Fate:__ Broke up in November 2013 __Kaitlynn Carter__ [#iframe://embed.gettyimages.com/embed/477237404?Ross landed his first major role as Ant in the 2006 comedy in November."I'm on team Katniss." PHOTOS: Best celebrity engagement rings of all time 3.They actually knew each other for years before their reality TV fame.
And although he was last linked to longtime love Cora Skinner, Ross seems to be smitten with single mom Simpson, who has a 4-year-old son with ex-husband Pete Wentz. Ashlee Simpson was pictured leaving Teddy's nightclub in Hollywood at a.m. In pictures taken by X17online.com, Simpson can be seen cozying up to the 24-year-old actor, who escorted her to their chauffeured car following an obviously fun night out.Simpson, 28, wore a flirty floral pantsuit, while Ross rocked patched jeans, a white T-shirt and a black jacket.Every July, the greatest wardrobe invention this side of 1776 emerges for a hot second: the American flag bikini.And this year has turned out to be a particularly Star-Spangled one.