A Justin Bieber rumour and a proposal gone wrong: Kourtney Kardashian's relationship history.

The Kardashian sisters are pretty well known for their drama-filled, high-profile relationships (among many other things). 

No one can forget Kim's 72-day marriage to Kris Humphries (not to mention her current divorce from Kanye West) or Khloé's two major relationships involving cheating allegations.

But now that Kourtney's in the most surprising relationship with Blink 182 drummer Travis Barker, we thought it was time to revisit her relationships prior. 

Let's start with the biggest one of them all: Scott Disick.

Watch the trailer for the first season of Keeping up with the Kardashians here. Post continues below.

Video via E!

Kourtney Kardashian, 42, and Scott Disick, 38, started dating way back in 2006 after meeting at Girls Gone Wild creator Joe Francis' house. However, there was no immediate spark.

"I just thought he was so annoying," Kourtney explained during an episode of Kourtney and Khloé Take the Hamptons. "He was four years younger, he lived in New York, he didn't have a job."


When Keeping Up With the Kardashians first aired in 2007, Disick was prominently featured as "Kourtney's boyfriend".

The couple appeared blissfully happy in the honeymoon stage of the relationship.


But that didn't last long.

Not even a year into their relationship, Disick was accused of cheating during an episode of the reality show, when Kardashian's sisters found texts on his phone that read: "I loved looking into your eyes last night. I wish I could come to LA for a week and not tell Kourt."

The two broke up and Kardashian went off to film Kourtney and Khloé Take Miami single.


Shortly after, the pair caught up in Miami and Kardashian fell pregnant with their first child, Mason. The surprise pregnancy ultimately led the couple to get back together.

Throughout her pregnancy, Kardashian and Disick had their problems - mostly stemming from Disick's alcohol and substance abuse, which was documented on the reality show.

On December 14, 2009, Mason Disick was born.

Remember this episode? Image: E!


In 2010, Kardashian and Disick split again, after a night where Disick excessively drank causing him to punch walls, while Kardashian and her sister Kim locked him out of the room to keep Mason safe.

"There’s not even a one per cent chance... I can’t do this anymore. I love Mason more than I love you and that’s what it is," she said during an episode of Kourtney and Khloé Take Miami.

The following year they were (you guessed it!) back on again. 

This time, Disick even proposed to Kardashian during a 2011 episode of Keeping Up With the Kardashians, however, she said no, explaining she had no interest in getting married.

While wedding bells weren't on the horizon, another baby was: Kardashian fell pregnant in 2011 and welcomed their daughter, Penelope, on July 8, 2012.


The following year, Disick lost both his parents in a matter of months. 

He explained that these two events drove him into a deep depression, and later become a large contributing factor for his substance abuse and their relationship problems.

In 2014, Kardashian announced she was pregnant with their third child. Disick did not handle the news well.

"You just keep suckering me into these kids," he told her on the show. "I can't handle all of this responsibility."

In December 2014, Reign Disick was born.


In 2015, the couple remained together despite their issues. 

They lived together while Kardashian filmed Kourtney and Khloé Take The Hamptons until Disick's substance abuse became too much and she kicked him out of the Hamptons home.

Shortly after, Disick admitted himself to rehab. After spending a month in rehab, Kardashian chose to stay by his side.


In July 2015, Disick was spotted partying with his ex-girlfriend Chloe Bartoli, a Los Angeles-based stylist, while in Monaco. Later that month, Disick and Kardashian split once again.

"Scott has been running around saying he's single," a source told E! News. "Kourtney dumped him after she saw the pics [in Monte Carlo] and he hasn't been home after a month-long party binge."

By December, rumours start swirling that Kardashian was dating Justin Bieber (yep, weird), with the singer fuelling the fire by posting a photo with the caption, "Lord knows". 


Throughout 2016, Scott posted various lovey-dovey photos with Kardashian, confusing precisely everyone.


By December 2016, they got back together briefly, until Disick was caught partying in Miami in February 2017, and they split again.

Soon after, reports emerged that Kardashian was dating 23-year-old boxer-turned-model Younes Bendjima. At the same time, Disick started dating 19-year-old model and social media personality Sofia Richie.


Throughout Kardashian's relationship with Bendjima, she posted various snaps of them on social media, despite never commenting on or confirming the relationship.


But after Kardashian shared a photo of herself - which Bendjima commented on (and later deleted) - the couple called it quits.


A year after the breakup, photos emerged of the couple hanging out again. However, sources shared it was nothing serious.

"Kourtney and Younes have always been in touch and friendly with each other," a source told E! News

"They reconnected after their split last year and remained friendly. He’s been to several of the family events, including Kourtney’s birthday, and he’s hung out with Kourtney a few times recently in social settings."

As of December 2019, that all changed, and the couple got back together, briefly, until they broke up again.

Fast forward to 2021, and Kardashian is dating Blink 182 drummer Travis Barker. And things look pretty serious.

You can read all about how they met and their apparent 'secret wedding' here.

Feature Image: Instagram.