Scott Disick and Kourtney Kardashian's complete relationship timeline—all of the ups and downs since 2006

Relive all of the Scott Disick Kourtney Kardashian drama before the KUWTK reunion on E!

LAS VEGAS, NV - DECEMBER 31: (EXCLUSIVE COVERAGE) Television personalities Scott Disick, Kourtney Kardashian celebrate New Year's Eve at the Sugar Factory American Brasserie at the Paris Las Vegas on December 31, 2011 in Las Vegas, Nevada. (Photo by David Becker/WireImage)
(Image credit: Getty Images)

Scott Disick, Kourtney Kardashian, and loyal reality TV fans everywhere have been through one hell of a romantic rollercoaster ride. The on-again-off-again couple has experienced a fair share of ups and downs over the years, from births and celebrations to heartache and scandals. 

Somehow through it all, Scott Disick remains a constant not only in Kourtney Kardashian's life but the entire Kardashians' lives. Though some are secretly hoping for their love story to be rekindled (sorry Travis Barker!), we're going to take a look at how it all began.

Scott Disick, Kourtney Kardashian, and Joe Francis in 2006

Kourtney and Scott's mutual friend and Girls Gone Wild creator Joe Francis is responsible for one of the most iconic relationships in reality TV history. The duo met at Francis' home in Mexico, though according to Elle Australia, Kourt wasn't terribly intrigued at first and found Scott to be annoying. That didn't last long—the two were linked shortly after. 


The romance was short-lived. Although the two seemed to be hitting it off in the debut season of Keeping Up with the Kardashians in 2007, cheating accusations swirled after Kourt found text messages from another woman on Scott's phone. The romance had ended...temporarily. 

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After crossing paths in Miami while filming Kourtney & Kim Take Miami, the two were back on once again, according to US Weekly. This is arguably one of the most important years in the two's lives, as they welcomed their first child together, a son named Mason.


The two went their separate ways—again—this time because of Scott's wild ways. His partying was becoming too out of control for Kourtney, though they did reconcile shortly after.

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Although Kourtney might've rejected Scott's attempted proposal at the time, per US Weekly, she didn't reject the idea of expanding her family. She announced later in the year that she was pregnant with her and Scott's second child.


An incredibly exciting time—the birth of the couple's daughter Penelope—arrived in 2012. What was such a joyous event was sadly followed by grief, as Kourtney was left to help Scott grieve the loss of his parents, both of whom died in 2013 just a few months apart from each other. 

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Kourtney was keen on growing her family for the third time, and the two welcomed a little boy named Reign in 2014. 

2015 and beyond

Despite their growing family, Kourtney and Scott officially called in quits in 2015. Since then, Scott has been linked to Chloe Bartoli, Sofia Richie, and currently, Amelia Hamlin. For her part, Kourtney sparked relationship rumors with Justin Bieber—though the two claim they've always been friends—dated Younes Bendjima, and most recently went public with her PDA-filled, friends-to-lovers relationship with Blink-182 drummer, Travis Barker. 

Although the two never quite managed to get on the same page, fans always noticed how Scott still managed to be a mainstay in the Kardashian dynamic as he and Kourtney co-parented their children. Some fans (and nudging sister Kim) always thought that there would be a happy ending for the two, but now that it looks like Kourt and Travis are on their way to an engagement, it's not so certain.

In a short snippet from the reunion special, which airs on June 17th at 8pm and June 20th at 9pm on E!, we hear host Andy Cohen ask Kourtney: "Do you think your relationship might have turned out differently if you hadn't shared so much of it?"

She replies: "Probably, but I think the substance abuse was the deal-breaker," in reference to Scott's issues with drinking. Disick, without hesitation, agreed. 

Whether or not they end up back together or not, we have a feeling the Kourtney and Scott journey is just getting started. 

Danielle Valente
Danielle Valente

Danielle is a news writer for woman&home and My Imperfect Life. When she's not working, you can find her experimenting with new recipes or sitting on the couch with a good book and a cup of coffee.