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The Timeline Of Kourtney Kardashian & Scott Disick's Relationship Is Truly A Rollercoaster

Celebrity relationships and friendships are a rare breed. These famous faces have their lives played out in front of the masses, whether it’s the good, the bad, or the straight-up shady. In Elite Daily’s new series, It’s Complicated, we’re highlighting the biggest celebrity “feuds” that took over Hollywood and dominated our Sunday brunches for weeks on end. We’ll take a deep dive into the lives and social media feeds of our favorite stars and dissect what happened in front of the camera, what went down behind the scenes, and everything you might have missed in between.

It’s no secret Kourtney Kardashian and Scott Disick have one of the best co-parenting relationships in Hollywood. They work hard to make sure they’re raising their kids to the best of their ability, even though they’re not an item anymore. But it has taken them a lot of effort and patience to get there. So, how did they end up where they are right now after so many years together(ish)? Well, the timeline of Kourtney Kardashian and Scott Disick’s relationship is certainly a bit of a rollercoaster.

Kardashian and Disick were together for 12 years and, in that time, they lived quite a life. They had three kids, plenty of fun, and lots of drama. While the romantic relationship between them didn’t quite work out, they still have a solid connection. In an April 2019 episode of Keeping Up with the Kardashians, a spiritual healer in Bali told them they were soulmates. The reaction from both of them was pretty positive, especially Kardashian's.

"I normally don't like this type of stuff, but I'm really trying to connect and improve my relationships," Kardashian said. "I don't know what the definition of 'soulmate' is, but Scott and I, we're going to be in each others' lives forever. Like, we are soulmates in a sense. No matter what. Whether we're ever together again or not."

So, how did this soulmate connection form? You need to examine Kardashian and Disick’s relationship as a whole to fully understand. Let’s see how it all started:

2006: Kardashian & Disick Meet In Mexico

Before they became the co-parenting experts they are today, Kardashian and Disick were just your ordinary singles looking for love. They actually found it through Kardashian’s ex Joe Francis, who was hosting a house party both were attending. This was back in 2006. The two met, hit it off, and the rest is history.

October 2007: Keeping Up With The Kardashians Premieres

In October 2007, Keeping Up With The Kardashians premiered on E!, and by then, Kardashian and Disick had already been an item for just about a year. Together, they went from enjoying relative obscurity to being world-famous, which likely added to their deep bond over the years.

November 2008 - August 2009: Kardashian & Disick Take A Break

After almost two years together, Kardashian and Disick decided to take a break from their romance. The reason? According to Us Weekly, it was the pressures of their long-distance relationship and suspicions Disick was cheating. The split was only temporary, though, and they reconciled in early 2009.

In August 2009, Kardashian and Disick announced on KUWTK that they were expecting their first child together.

December 2009: Kardashian & Disick Welcome Baby Mason

In December 2009, Kardashian and Disick welcomed a baby boy, who everyone now knows as Mason Disick. The couple was over the moon when he was born, but that baby bliss didn’t last too long.

2010: The Relationship Gets A Rocky

According to Cosmopolitan, 2010 proved to be a tough year for Kardashian and Disick. At the time, Kardashian was starring in Kourtney And Khloé Take Miami, so all of their ups and downs were chronicled on the show.

One episode, in particular, showed Kardashian grappling with Disick’s excessive drinking. Apparently, Kardashian struggled to figure out the best way to handle the situation. Eventually, she decided to use Mason and their family’s well-being as leverage to help Disick understand the gravity of the situation.

"You're not going to be around Mason while you're working on yourself," she told him. "There's not even a 1% chance... I can't do this anymore. I love Mason more than I love you. And that's what it is."

Thankfully, Kardashian and Disick’s relationship was able to survive all those ups and downs.

November 2011: Kardashian & Disick Reveal They’re Expecting Again

After rumors began circulating that Kardashian was expecting her second child, she finally confirmed the pregnancy in a statement to E! News.

"Scott and I are so excited to announce that we are expecting our second child and are thrilled to be expanding the love in our family," she said.

July 2012: Baby Penelope Is Born

Kardashian and Disick welcomed Penelope in July 2012, making the Disicks a family of four.

2013 - 2014: Disick Loses His Parents

Disick unfortunately lost both of his parents within three months of each other. His mom, Bonnie Disick, passed away in October 2013. Three months later, his father Jeffrey Disick also passed.

June 2014: Kardashian and Disick Are Expecting Again

Just a few months after Disick lost his parents, a source told Us Weekly that he and Kardashian were adding yet another little one to their family.

"It was planned," the source said at the time. "[Kourtney] wants to have a handful of kids."

November 2014: Disick Checks Into Rehab

According to E! News, Disick checked into rehab for “alcohol and drug-related issues.” The ordeal was documented on Kourtney & Khloé Take The Hamptons and Kardashian had some strong words to say about it.

"This behavior has been going on for years," Kardashian said on the show.

Disick didn't try to deny his unacceptable behavior. "I've pretty much become a broken record and I'm sick of hearing myself," he admitted.

December 2014: Baby Reign Is Born

On Dec. 14, 2014, the couple’s second son, Reign, was born. Funnily enough, Mason was also born on the same day five years prior!

July 2015: Kardashian & Disick Call It Quits For Good

In July 2015, just seven months after Reign was born, Kardashian and Disick went their separate ways.

2015 - 2019

In the years since the breakup, Kardashian and Disick have found ways to support and love each other from a distance. They’ve both moved on to other people romantically, though.

Disick is dating Sofia Richie, while Kardashian was most recently linked to Luka Sabbat. She also dated Younes Bendjima for nearly two years. Beyond that, though, they frequently come together for the sake of their kids.

In a recent Q&A with each other for Kardashian’s new business Poosh, Disick explained why co-parenting is so important to them.

"I'm not gonna make our kids miss out on things just because we couldn't figure out how to be a couple," he said. "And by the way, I don't think people will be able to live their lives if they do it that way maybe, so it's not our [place] to tell other people how they wanna live."

These lifelong partners have definitely figured out a way to make things work for them and their kids, which is all that matters.

Caroline Wurtzel/Elite Daily