A definitive timeline of Scott Disick and Kourtney Kardashian’s on-again, off-again relationship

10 September 2018
By Fashion Quarterly


When it comes to dysfunctional on-again, off-again couples, Kourtney Kardashian and Scott Disick rule the roost.

That said, we can’t help but feel like they belong together. After all, they do share three beautiful children. Also, come on, Scott and Kourt have always been the most entertaining!

Kim Kardashian and Kanye West? Yawn. Khloé Kardashian and Tristan Thompson? Media nightmare. Kylie Jenner and Travis Scott? Please. The Lord and his OG lady are where it’s at. So in the spirit of that, we’re breaking down a definitive timeline of their relationship.

Scroll for the timeline of Scott Disick and Kourtney Kardashian’s relationship.


It all began in the simpler days of 2006. Kourtney met her future baby daddy at Joe Francis’ house in Mexico and shortly thereafter, they began dating. “I introduced Kourtney [Kardashian] and Scott [Disick] at my house in Mexico,” the Girls Gone Wild mogul told In Touch. “Scott came as the guest as a friend of mine, and they met in my master bedroom.”


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#FBF The night I met @letthelordbewithyou 😍.

A post shared by Kourtney Kardashian (@kourtneykardash) on


Aside from a brief pregnancy scare in 2007, things were pretty much fine and dandy with Scott and Kourt until 2009. Sigh, we miss those days. Basically, the couple broke up for the first time after Kourtney caught Scott texting some random woman who he had saved as “My Wife” in his phone. Later that year, they rekindled their romance after the birth of their first child, Mason Disick.

At first, it seemed like they were going to make it work, but things took a dark turn. Kourtney couldn’t handle Scott’s out of control behaviour and drinking in 2010 — especially now that he was a father. “There’s not even a one percent chance… I can’t do this anymore. I love Mason more than I love you and that’s what it is,” she told the now-35-year-old in an episode of Kourtney and Khloé Take Miami.


Fast forward to 2011: Scott impulsively proposes to Kourtney, she turns him down, and the Earth keeps spinning. While Kourt didn’t want to marry Scott, she was willing to have another one of his babies. Go figure! Their second child, Penelope Disick, was later born in 2012.


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time flies

A post shared by Kourtney Kardashian (@kourtneykardash) on


Sadly, the end of 2013 and beginning of 2014 was an incredibly difficult time for Scott. Within just a few short months, he lost both his mother and father. Naturally, Kourtney was by his side every step of the way and the pair became closer than ever. By the end of that year, their third child, Reign Disick, was born.

Now, from the end of 2014 to about 2016 is where things got really rocky. We’re just going to highlight the biggies, Okay? Scott was in and out of rehab at least two times, he was rumoured to have been dating both Lindsay Vrckovnik and Chloe Bartoli, and his partying persisted. While Scott was making an ass of himself, Kourtney was reportedly hooking up with Justin Bieber. Talk about a curveball, huh?


Nothing all that revolutionary happened again until spring 2017 when Kourtney and Scott revealed that while they were no longer involved romantically, they were successfully co-parenting.


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MOM and DAD back at it again with the coparenting skills.

A post shared by Kourtney Kardashian (@kourtneykardash) on

That brings us to May 2017 when Kourtney was first spotted with Younes Bendjima, 25. At first, it seemed the pair was just hooking up but as we all know, they stayed together until August 2018. As of Aug. 7, the pair has reportedly split amid some scandalous behaviour on Younes’ part.

Scott, of course, also linked up Sofia Richie, 19, around May 2017 and apparently they’re still going strong. However, on the highly anticipated Season 15 premiere of Keeping Up with the Kardashians, Scott did allude to the fact that there’s a chance that he and Kourt could get back together one day.

“We always said we’d try to get back together when we’re 40,” Scott revealed. Although, he did go on to say that Kourt is “crazy”… so, yeah, we’re not exactly sure what to think. What we do know, is that the former flames were spotted hanging out at Kylie Jenner’s 21st birthday party on Aug. 9.

Uh, can you say progress?! Khloé even captioned a pic of the pair with “A girl can dream.” That’s major, guys. When your own sister is shipping you and your ex, you know it’s time to reconsider the breakup!

Words: Melissa Copelton
Photos: Getty Images, Instagram

This article originally appeared in Life & Style.

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