Kourtney Kardashian and Scott Disick’s Relationship Timeline: A Look Back

They met at a party in 2006 and were inseparable for 10 years.

<p>Getty Images</p>

Getty Images

Kourtney Kardashian and Scott Disick’s relationship is a cornerstone of 2010s pop culture. Having been together for almost a decade and parenting three kids together, there’s a lot of ground to cover—but it all started at a party in 2006.

The two hit it off on that fateful night and proceeded to date on and off until 2015, but not before airing out all the trials and tribulations on the hit TV series, Keeping Up With The Kardashians. The now-exes have remained friendly and now cordially co-parent their kids – Mason, Penelope, and Reign—even through their multiple relationships, including Kourtney marrying Blink-182 drummer Travis Barker back in May 2022 and Scott notably dating Sofia Richie on-and-off from 2017 to 2020.

Buckle up, there’s a lot more to the story. Here’s a look back at Kourtney Kardashian and Scott Disick’s relationship timeline.

2006: Kourtney Kardashian and Scott Disick meet in Mexico.

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In Mexico sometime in 2006, California girl Kourtney and New York native Scott met for the first time at a party thrown by a mutual friend, the Girls Gone Wild founder, Joe Francis. Kourtney later shared a photo of the first meeting on Instagram, where the soon-to-be couple is seen sitting on opposite ends of the couch. On a later episode of Kourtney & Khloe Take the Hamptons, Kourtney admits she wasn’t interested in Scott because she “thought he was annoying.” Seems that sentiment didn’t last long!

October 2007: Scott Appears on Keeping Up With The Kardashians as Kourtney’s boyfriend.

<p>Jean Baptiste Lacroix/Getty Images</p>

Jean Baptiste Lacroix/Getty Images

Nearly a year later, Keeping Up With The Kardashians graces our TV screens – and Kourtney debuts Scott as her boyfriend in the very first episode. "We were friends for about a year and then started dating, and have been together ever since," she said in the premiere.

November 2007: Kourtney and Scott almost tie the knot in Vegas.

<p>Frazer Harrison/Getty Images</p>

Frazer Harrison/Getty Images

Continuing to share their relationship in real time on KUWTK, Scott asked Kourtney if she wanted to marry him after partying in Las Vegas. On the episode, Kourtney initially agrees to the proposal, and even checks out the infamous Little White Chapel with her sisters, Khloe and Kim, as well as her mom, Kris. However, the couple never made it down the aisle, having agreed that the nuptials felt a bit rushed.

March 2008: Kourtney and Scott split for the first time.

<p>Jean Baptiste Lacroix/Getty Image</p>

Jean Baptiste Lacroix/Getty Image

On the season 2 premiere of KUWTK, Kourtney finds texts from another woman on Scott’s phone and accuses him of cheating while she was away in the Hamptons. Kourtney confronts Scott and the two split for the first time.

August 2009: Kourtney and Scott rekindle in Miami.

<p>Chris Polk/Getty Images</p>

Chris Polk/Getty Images

Though fans suspect the lovebirds rekindled much sooner, Kourtney and Scott officially got back together in August 2009 in Miami. As seen on an episode of Kourtney & Kim Take Miami, the couple was caught hooking up at a party. Shortly following, Kourtney and Scott announced they were expecting their first child after Kourtney noted she had forgotten to take her both control pills months earlier.

December 2009: They welcome their first baby, Mason Disick.

Amid their rekindled romance, Kourtney and Scott became first-time parents when they welcomed their son, Mason Disick to the world on December 14, 2009. Weighing in at 7lbs, 6 oz, and measuring at 19.5 inches long, the first Kardashian grandchild was born a whopping nine days ahead of his original due date. Of course, this momentous milestone was captured on KUWTK, including when Kourtney notably pulled the baby out herself during birth.

August 2010: Kourtney and Scott break up again – and get back together shortly after.

<p>Ethan Miller/Getty Images</p>

Ethan Miller/Getty Images

Things turn sour shortly after with Scott’s substance abuse problems taking a toll on his relationship with Kourtney. In an episode of Kourtney and Kim Take Miami, Kourtney calls it quits with Scott for the second time after a night of drinking, which led to him punching a mirror.

Kourtney threatened that the relationship was over until Scott got help for his substance abuse. A few days after the episode aired, the couple announced that they were working on their relationship. Scott was abstaining from drinking and the new parents were attending couples therapy.

April 2011: Scott considers proposing to Kourtney.

<p>David Becker/Getty Images</p>

David Becker/Getty Images

On the season one finale of Kourtney and Kim Take New York, Scott shops for engagement rings with the hopes of proposing while celebrating his anniversary with Kourtney. However, he was never given the chance, as Kourtney revealed she was content with their current life as-is.

"Things are so good now and we have finally come to this place, why would we want to change that," Kardashian said in the episode. "I just feel like right now I'm pretty happy with the way things are."

July 2012: Kourtney and Scott welcome their first daughter, Penelope Disick.

<p>Bauer-Griffin/Getty Images</p>

Bauer-Griffin/Getty Images

Almost two years after their son was born, Kourtney and Scott welcomed their second child, a baby girl named Penelope Disick, on July 8, 2012. Weighing in at 7lbs and 14oz, she was delivered via an unmedicated birth in Los Angeles. The entire Kardashian clan was in attendance at the hospital for the family’s first granddaughter.

December 2014: Kourtney and Scott welcome their second baby boy, Reign Disick.

Shortly after the loss of both of Scott’s parents – his mother Bonnie passed away in 2013 and three months later his father Jeffery followed suit – the couple welcomed their third baby and second son, Reign Disick, on December 14, 2014. Officially a family of five, their youngest was born on the same exact day their oldest, Mason, turned five years old.

July 2015: Kourtney ends her relationship with Scott following cheating rumors.

<p>David Krieger/Getty Images</p>

David Krieger/Getty Images

After almost ten years together, the reality stars break up for good after photos emerged of Scott with his ex-girlfriend Chloe Bartoli in Monte Carlo. Kourtney broke off the relationship after welcoming three kids together, and the split was featured on KUWTK, naturally. During this time, those closest to Scott worried he had fallen off the wagon and was back to his old patterns of substance abuse.

October 2015: Scott checks himself Into rehab amid breakup.

<p>Bauer-Griffin/Getty Images</p>

Bauer-Griffin/Getty Images

Amid his blowout breakup with Kourtney, Scott checks himself into rehab for his substance abuse problems. Scott checked into Cliffside Malibu, a luxury drug and alcohol rehab center, after concerns he wouldn’t be able to see his children if he did not receive help. Kourtney was reportedly considering seeking sole custody at this time.

November 2018: The duo are co-parenting in stride.

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Fast forward through various relationships and many ups and downs, the couple came to a mutual understanding in order to co-parent their three children. Taking family vacations together, attending group dinners and celebrating holidays as a family, the two seemingly hit their stride as exes.

Kourtney is now married to drummer Travis Barker, with whom she welcomed her fourth child, Rocky Barker, in November 2023. Scott has dated a variety of Hollywood stars – including Sofia Richie, Bella Thorne, and Amelia Hamlin.

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