From bromance to romance! 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.
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. The now-married mom of three has since described the year-and-a-half romance as her "first mature relationship." They split in 2006.
2006: Brody Dates Childhood Pal Nicole Richie
After his split from Cavallari, Jenner briefly dated his childhood pal Nicole Richie, who he's known since he was 2, in 2006. However, their relationship was short-lived, and the two decided they were better off as friends.
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. In July 2015, Jenner told Yahoo Style: "A lot of that show was scripted. A lot of it was improv. Lauren’s a dear friend of mine, and it was pretty funny to have to live that reality. We were just friends. We’d film a scene of us kissing or being in this lovey-dovey scene, and then right after it would be like, ‘Cut,’ and we’d be like, ‘Great to see you,’ and we’d go our separate ways."
After Conrad left the show, Cavallari took over as the lead, and she and Jenner revived their romance — on camera, at least. "They pretended that him and Jayde [Nicole] broke up and I was dating Brody, and Jayde and I got into a huge fight because she saw us in a club," Cavallari told Bethenny Frankel in 2013. "It wasn't real at all. They were together the entire time." (He and Playboy Playmate Nicole dated for about a year until late 2009.)
2009: The Year of the Bromance
After skyrocketing to fame, Jenner starred in his own reality series, Bromance, which he executive-produced from 2008 to 2009. The Bachelor-style series chronicled a bunch of contestants vying to become Jenner's best friend through a series of challenges.
2010 to 2012: Things Get Complicated With Avril Lavigne
Jenner and the "Complicated" singer dated for two years before Us Weekly broke the news in January 2012 that they had ended their relationship. "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. "Avril didn't like that," the same insider told Us.
2013: The Jenner Brothers Join Keeping Up With the Kardashians
Brody, his brother Brandon and Brandon's wife, Leah Jenner, all joined season 8 of E!'s KUWTK in 2013. Brody was spotlighted interacting with his stepsiblings and half siblings, but mostly grappling with his broken relationship with his father and his stepmom at the time, Kris Jenner.
He finally found his match! Jenner started dating the pretty blonde model two years ago. In a 2015 interview with GQ, he spilled some bedroom secrets, including how the two were open to threesomes. "I'd have to say [the best sex I’ve ever had is] with my girlfriend, Kaitlynn,” Jenner told the mag. “We have the best sex together, but we also switch it up and do fun things as well. We're not opposed to having somebody else join in on our sexcapades."
While Jenner was serious about his romance with Carter, his family members weren't too sure it would last. Stepsister Kim Kardashian famously denied Brody a plus-one to her lavish wedding to Kanye West, resulting in some family drama. However, the couple stood the test of time and will be tying the knot in the future.
2016: Brody Gets Engaged
Jenner proposed to his girlfriend during a romantic tropical getaway. "On May 4th 2016 I got engaged to my lover and my best friend @kaitlynn_carter," he announced Friday, May 6. "I couldn't be more in love with this woman and I can't wait to spend the rest of my life with her."
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