Kourtney Kardashian and Scott Disick’s complicated relationship goes back more than a decade. The on-again, off-again pair has gone through their ups and downs over the years, with cheating scandals, three children, a reality show and much more in between.
Their sometimes love story began back in 2006 when Kardashian met Disick at a house party hosted by Girls Gone Wild founder Joe Francis.
“I introduced Kourtney and Scott at my house in Mexico,” Francis previously told In Touch. “Scott came as the guest of a friend of mine, and they met in my master bedroom.”
While Disick said on a 2014 episode of Kourtney and Khloe Take the Hamptons that he “liked” Kardashian right away, he admitted that she “wanted noting to do” with him initially.
“I just thought he was so annoying,” Kardashian said. “He was four years younger, he lived in New York, he didn’t have a job.”
Despite Kardashian’s initial dislike, she and Disick were dating when her family’s reality show, Keeping Up With the Kardashians, premiered in October 2007. During the season, the then-couple had a pregnancy scare, though their first child wouldn’t be born until years later.
Season 2 of the series documented the first potential infidelity for the couple when Kardashian saw romantic messages in Disick’s phone that were sent to someone labeled as “My Wife” in his contacts. The scandal eventually led to the pair’s 2008 breakup.
In 2009, though, the on-again couple announced that they were pregnant with their first child. The pair welcomed Mason Dash Disick on Dec. 14, 2009.
Things weren’t all good for the growing family, though, as Kardashian called out Disick’s excessive drinking and partying after he punched a mirror.
“I can’t do this anymore,” she said during an episode of Kourtney and Khloe Take Miami. “I love Mason more than I love you.”
The pair went on to announce their second pregnancy in 2011, with Kardashian telling 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.”
Penelope Scotland Disick was born on July 8, 2012. Less than a year after welcoming Penelope, both of Disick’s parents died, leaving the reality star in an unstable condition. In fact, Disick didn’t even return home after Kardashian told him they were expecting their third bundle of joy in 2014.
The ordeal led Disick to check into rehab that year, but he left before the birth of his third child, Reign Aston Disick, on Dec. 14, 2014.
Just three months later, Disick went back to rehab, this time in Costa Rica, where he stayed for one week.
It wasn’t enough to keep Kardashian around, though, as the pair called it quits in July 2015 after pictures turned up of Disick canoodling with his ex, stylist Chloe Bartoli, in Monte Carlo.
“I f**ked up,” Disick told Kardashian on KUWTK after the photos were made public. “I made the worst decision I’ve ever made in my life.”
In November 2015, Disick completed one month of rehab in Malibu, California, but a source told 360aproko the next month that “Kourtney hasn’t let Scott back in with open arms,” despite some seemingly friendly outings.
“They’re not ‘not together,’ but they’re not ‘together’ — they’re not seeing other people, but at the same time she’s not ready to take him right back,” the source said. “She’s still making sure he’s OK. He’s still making sure he’s OK. It’s going to be a long road but he’s doing well.”
“This is the first time he’s being smart about it and everyone is hoping it lasts,” the source added. “Scott is trying to lose his party boy image. He’s doing that for himself, too.”
In January 2016, a source told 360aproko that Kardashian was “100 percent” over her ex and had “completely moved on.”
“This breakup has really showed her that she needs to focus on herself,” the source said. “She’s spending a lot of time with her girlfriends, is planning dinners and nights out. She’s happy and glowing.”
In contrast, the source said Disick was in “a dark place,” but noted that he and Kardashian “will always have a cordial relationship for the kids.”
That same month, Kardashian shared a pic of herself with Disick “before he was a baby daddy.”
From there, Kardashian house hunted with Disick, hosted him at a family dinner, had a flirty hangout with him, and spent time with him and their kids.
In April 2016, Kardashian said she was “friends” with Disick and even hinted that they may get back together.
“We’re not getting back together right now, but I don’t know, like, what the future holds in life,” she said on the Today show. “But we’re just doing our best to be the best parents.”
That same month, Disick shared a photo of himself kissing Kardashian for her birthday. She reciprocated with a steamy pic for Disick’s birthday the next month. They even went on a family vacation together.
In the October 2016 issue of Cosmopolitan, Kardashian once again expressed hope about a potential reconciliation with Disick.
“The idea of having my family together is amazing, but it’s not the way things ended up,” she said. “They may end up there. I’m not sure. To me, it’s in God’s hands. If it’s meant to be, then things will line up.”
“We definitely tried for a long time,” she added. “But relationships are exhausting! Being able to focus on the kids and me right now is good. We say to each other all the time, ‘I’m the coolest ex-girlfriend/baby mama you could ever ask for!'”
Despite the uncertainty, Kardashian said she and Disick were “so not there” in regard to getting into new relationships.
Later that year, the former couple did get there, though, when Kardashian embarked on her first serious post-Disick relationship with Younes Bendjima. The next year, Disick began dating Sofia Richie.
While Kardashian and Bendjima called it quits in August 2018, things remained solid between her and Disick, until he introduced Richie to their kids without Kardashian’s permission. Despite that fight, Kardashian accompanied Disick and Richie on a Mexican vacation in December 2018.
“The trip was really fun and easy,” she said on KUWTK. “I know we don’t have to travel together, and I don’t think we’ll take every trip together, but it was totally not awkward. We’re doing our best to make everything feel super normal for the kids.”
Following their trip, Kardashian and Disick opened up about their co-parenting philosophy in a video for Poosh.
“I’m not gonna make our kids miss out on things just because we couldn’t figure out how to be a couple,” Disick 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.”
The two women in Disick’s life teamed up in May 2020 to encourage him to seek help for his “substance abuse issues,” according to a source.
“Kourtney and Sofia were a big proponent in having Scott enter rehab in Colorado,” the source said. “At the end of the day, Scott needs to be clean to be around his children and family and that’s everyone’s main focus right now… is Scott’s sobriety and the kids having a healthy father.”
Disick and Richie didn’t last much longer, though, calling it quits later that month. Since then, speculation has once again swirled about a possible romance between Kardashian and Disick.
They have traveled to Utah, celebrated his 37th birthday, and been flirty on social media more than once.
