Brody Jenner is comfortable in front of the cameras, and he has been a reality TV star even before the Kardashians got their taste of fame. Over the years, we have seen many of his relationships play out in a very public way, either becoming a storyline on The Hills (and later on the reboot The Hills: New Beginnings) or shared on social media.

Jenner doesn’t try and hide his affection for the women in his life either, and he has been spotted on PDA-filled dates numerous times. There have been a lot of interesting (and often surprising) women who Jenner has been linked to, from Nicole Richie to Avril Lavigne, and below are 20 photos of the beautiful women who’ve been a part of Brody Jenner’s life, although some didn’t last long!

20 Growing Up, Brody Jenner Was More Than Friends With Nicole Richie

Brody Jenner has been linked to several beautiful women over the years, but one of his first romances was with Nicole Richie. According to People, Jenner and Richie had known each other since they were toddlers and briefly dated in 2006. They ended things on good terms and decided they were better as friends.

19 ‘The Hills’ Fans Were Interested In What Was Happening With Brody And Lauren Conrad

Fans of The Hills will be familiar with the storyline involving Brody Jenner and Lauren Conrad, and everyone was curious to find out whether they would stay together or not (or if it was all just for the cameras). They didn’t, and CheatSheet notes that they were only linked for a few months before things "fizzled out."

18 Their Relationship Was Short-Lived Because They Had ‘Zero Chemistry’

After hearing Lauren Conrad’s comments on the coupling, it’s not surprising that her relationship with Brody Jenner didn’t work out. In The Hills: That Was Then, This Is Now special (via Yahoo!), Conrad said that although she had a crush on Jenner, they “had zero chemistry." She added that they were friends, and she knew the show made it look like “more than it was.”

17 Josie Canseco And Brody Jenner Only Had Eyes For Each Other (Until They Didn’t)

Brody Jenner’s most recent romance was with Josie Canseco, and according to People, they started dating after his breakup from Kaitlynn Carter. There is a 14-year age gap between these two, but they were first linked after being introduced by a mutual friend, Frankie Delgado. In October 2019, it was announced that they had split.

16 He Celebrated His Birthday With His Much Younger Girlfriend

Although Josie Canseco and Brody Jenner’s relationship didn’t last long, they did appear to be really into each other (for the three months they were together). They were also spotted together at Jenner’s 36th birthday party, and an insider told People the pair were not shy about PDA during the celebration.

15 Brody Jenner Was Linked To Kristin Cavallari When He First Got A Taste Of Fame

Brody Jenner and Kristin Cavallari had a bit of a flirtation on The Hills, but according to CheatSheetit was all for the show. Before this, the pair did date for real. “I dated Brody when I was 18 right after Laguna Beach, and that’s it,” Cavallari said. “On the show, they had us dating for a few episodes… which wasn’t real at all.”

14 He Got Down On One Knee During A Tropical Vacation And Asked Kaitlynn Carter To Marry Him

There have been a few famous women who share a history with Brody Jenner, but his most serious relationship was with Kaitlynn Carter. According to Refinery29, the former couple met at a party in 2013. After three years of dating, Jenner proposed to Carter during a romantic vacation.

13 Josie And Her Man Enjoyed A Good Night Out On The Town

Josie Canseco and Brody Jenner didn’t try to hide their relationship and were spotted in public several times over the few months they were together. Their outings included a date in West Hollywood. According to Daily Mail, the couple met up with friends. They also made their relationship social media official, sharing posts and videos.

12 He Was So Serious About Jayde Nicole, He Got A Tattoo In Her Honor

At some point, Brody Jenner must have looked at Jayde Nicole and thought this was going to be the woman he would spend his life with. Why else would he decide to get a tattoo in her honor?! According to The Hollywood Gossip, the couple got matching tattoos of each other’s initials inked inside their lower lips. Um... how romantic!

11 They Weren’t Shy About Letting Their Relationship Play Out On TV

Brody Jenner is not a particularly private person– after all, he has been the star of a reality TV show– so it shouldn’t come as much of a surprise that he was willing to let fans into his relationship with Jayde Nicole. Us Weekly notes that they were together for around 15 months, and The Hills fans saw them fighting in the fifth season.

10 Bryana Holly Held Brody Jenner’s Attention (And Possibly His Heart) For A While

Brody Jenner’s relationship with Bryana Holly didn’t last long. The pair were linked in 2013, and according to Us Weekly, dated for just four months before breaking up. Still, despite it being a short-lived romance, the couple were really into each other, with the publication noting that they enjoyed a PDA-filled trip to Hawaii.

9 It’s Still Hard To Believe Brody Jenner And Avril Lavigne Were Once A Couple

It’s still hard to believe that Brody Jenner and Avril Lavigne were a couple, because they seem like such an unlikely match. But the saying opposites attract is right in this instance. It wasn’t just a brief fling either, as Us Weekly notes the pair were linked for years. Their breakup was announced in 2012.

8 They Dated For Over Two Years Before They Figured It Was Never Going To Work

Avril Lavigne and Brody Jenner figured out their relationship was not going to work in January 2012. At the time, an Us Weekly insider shed light on the breakup. “It was mutual, but Brody really broke up with her,” Jenner’s unnamed friend told the publication. The reason? Jenner wanted to focus on his career and didn’t go with Lavigne on her Asia tour.

7 Brody Was Kristin’s ‘First Real Love,’ Apparently!

Brody Jenner and Kristin Cavallari ended their relationship in 2006, although People reports years later they were seen flirting on The Hills — Cavallari has stated that this flirtation was all for the cameras and to create a storyline.

But at some point, Cavallari cared for Jenner, a lot. According to People, she has referred to Jenner as her first “real love.”

6 There Was A Time When Brody And Kaitlynn Carter Were Completely In Love...

Brody Jenner and Kaitlynn Carter got married in Indonesia (although Refinery29 notes that their marriage was never legal in the United States), but broke up after one year of marriage. In an essay for Elle, Carter had lovely things to say about her ex, writing, “He was quite possibly the most beautiful man on the planet, with a heart of gold and a tireless sense of adventure. I was drawn to his spirit.”

5 ...A Lot Has Changed Since Then

Even before Brody Jenner and Kaitlynn Carter announced their decision to split in 2019, it was clear that they had things they needed to work on in their relationship. Teen Vogue notes that they faced challenges on The Hills: New Beginnings, and there were “scenes depicting stress in their marriage.”

4 Brody Has Had No Shortage Of Famous Relationships

Remember we mentioned that Brody Jenner was not a private person? Well, this statement can be backed up by the claim he made with regards to Kaitlynn Carter and his willingness to speak about the birds and the bees (via Us Weekly). Jenner is candid about many aspects of his life, including the women he dates.

3 His Mama Liked Nicole Richie (But They Were So Young When They Got Together)

Nicole Richie and Brody Jenner were friends from a young age, and there was a brief moment when their relationship became something more. It didn’t work out, but the coupling had Jenner’s mama’s approval. Linda Thompson told People, “I think they’re very cute (as a couple). Will they get married? Who knows? He’s young, and so is she.”

2 He Dated His Sister-In-Law, Leah, When They Were Kids

Leah Jenner is married to Brody’s brother, Brandon, but before they were a couple, she was briefly linked to Brody. Although the story may sound like it would make for an extremely awkward situation at family gatherings, the pair were linked back in 1994, in the fifth grade. Leah said on the podcast, The Brody Jenner Podcast With Dr. Mike Dow (via SheKnows), “He was my boyfriend in the fifth grade, Brody was [but] we never kissed.”

1 Hey Brody, Why’d You Have To Go And Make Your Relationships So Complicated?

Avril Lavigne and Brody Jenner split after almost two years of dating, and when the news of the breakup was reported, E! News pointed something out. Jenner had a tattoo of Lavigne’s name on his arm, and Lavigne had one of Jenner’s name on her stomach. Why Brody Jenner continued to make his life complicated by getting tattoos of his girlfriends’ names, only he can answer.

Sources: People, Glamour, Yahoo!, CheatSheet, Refinery29, Daily Mail, The Hollywood Gossip, Us Weekly, Elle, Teen Vogue, SheKnows, E! News.

Next 10 Surprising Facts About Elvis Presley