Kourtney Kardashian and Scott Disick have been through the ringer. When the former couple met at a party thrown by Girls Gone Wild creator Joe Francis in Mexico in 2006, they had no idea that their lives would never be the same.
They took Us on their journey as they broke up, got back together, welcomed not one, not two, but three babies together and learned how to be in each other’s lives — even if it wasn’t as a couple.
Though they ultimately made the choice to split for good in 2015, finding several other partners since (Disick notably dated Sofia Richie on-and-off from 2017 to 2020), Kardashian and Disick managed to parlay their former romance into a successful coparenting relationship to the benefit of their three shared children, Mason, Penelope and Reign.
Scroll through to relive every step of the former pair’s long (and sometimes tumultuous!) relationship, for better or worse.
It all began in 2006, when Kardashian met Disick at a party thrown by Girls Gone Wild's Francis in Mexico.
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Our lives were forever changed in October 2007 when Keeping Up With the Kardashians debuted on E!, introducing the world to the famous Kardashian clan — and Disick.
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Kardashian accused her boyfriend of cheating on her on the season 2 premiere of KUWTK after she found texts from another woman on his phone. The pair split shortly after.
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The couple reconciled when they hooked up at a party in Miami, as seen on a September 2009 episode of Kourtney & Kim Take Miami. Shortly after, Kardashian, who had forgotten to take her birth control pill, announced that she was expecting. "I love being pregnant," she told Us Weekly of her first pregnancy. "I feel like it's going by too fast. It is the best thing that's happened to me. It's such a spiritual thing happening in your body, and it's what your body is made for."
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The on-again, off-again couple welcomed their first child, Mason, who entered the world weighing in at 7 pounds, 6 ounces and 19.5 inches long, in December 2009.
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Kardashian and her rekindled love moved to Miami for a fresh start, but by the summer 2010, things had gone sour once more when Disick’s partying became out of control. He punched a mirror in an August 2010 episode of Kourtney & Khloé Take Miami, and Kardashian had had enough. She later took him back.
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On the season 1 finale of Kourtney and Kim Take New York, Disick shops for an engagement ring for his beloved, but his hopes of a proposal are dashed by a conversation the two have about marriage over dinner. "Why mess it up?” Kardashian asked him. "I just feel like right now I'm happy with the way things are.”
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The couple exclusively confirmed to Us in November 2011 that they were expecting their second child. "It wasn't like we weren't trying," the expectant dad told Us at the time. "We kind of just said, 'If it's meant to be, it'll be.'"
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The couple welcomed their second child together, a baby girl named Penelope. A source told Us at the time, "The entire Kardashian/Jenner clan was at the hospital and everyone was super excited!"
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Disick’s mother, Bonnie Disick, passed away in 2013. Three months later, his father, Jeffrey Disick, followed suit, leaving Scott’s children as his immediate family.
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Us revealed that Kardashian and Disick would be parents to yet another little one in July 2014. "It was planned,” a source told Us at the time. “[Kourtney] wants to have a handful of kids.”
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The twosome called in quits for good in July 2015 after nine years when pictures surfaced of Disick getting cozy with his ex-girlfriend Chloe Bartoli in Monte Carlo. "[She's] hanging in there,” Kardashian's mom, Kris Jenner, told Entertainment Tonight at the time.
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Exactly five years after her first child was born, Kardashian gave birth once more, on Mason’s birthday. “Madly in love with my little Reign Aston Disick,” she wrote on Instagram of the pair’s third child.
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By the end 2015, Kardashian had moved on — with her sister Kendall Jenner’s pal, Justin Bieber! “Justin and Kourtney have been hooking up since late August, early September,” a source tells Us. The news made Scott none too happy. “Scott feels she’s doing this to get back at him and get revenge,” an insider told Us. “He feels he has to take it and can’t say anything after all he did to her, but he thinks it’s dumb and immature.”
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Disick took control of his alcohol and drug issues in October 2015 by entering rehab as Kardashian looked after their shared children.
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Kardashian began dating her first serious boyfriend since Disick — Younes Bendjima. The couple went on to date for nearly two years before splitting in August 2018.
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Disick went on a spree of hookups and courtships in 2017, most notably with Bella Thorne, who later said the two never had sex. It did little to bring Disick and Kourtney close, however, with the two feuding over their respective hookups in an October 2017 episode of the show, in which Kim Kardashian also mocked Scott for taking Thorne to Cannes.
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In September 2017, Us revealed that Disick had a new lady in his life — now-girlfriend Richie. It didn’t hurt his relationship with Kourtney, however: “Kourtney thinks this fling with Sofia is a little weird, but nothing shocks her anymore,” a source told Us exclusively. “Kourtney just wants Scott to be his old self. She shares three kids with him, so she’ll always want the best for him and will always make sure he’s happy.”
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Things had calmed down between the two by October 2017, when Kourtney shared a photo of herself and her former flame enjoying the great outdoors. “MOM and DAD back at it again with the coparenting skills,” she wrote on Instagram.
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The former couple defined their relationship rules in a March 2018 episode of KUWTK in which Kourtney asked Disick not to go into her bedroom without permission. The businessman agrees: “There’s obviously some boundaries that we both need to respect, and I don’t want you to be uncomfortable.”
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Khloé Kardashian trolled the ex-lovebirds to get back together in a series of Instagram Stories about Kendall's 21st birthday. “A girl can dream,” she wrote of the duo at the time.
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Despite both having significant others at the time, Kim revealed in a September 2018 episode of the hit E! series that Disick had expressed interest in having a fourth child with his ex. “So Scott just texted me that he wants to have another baby with Kourtney … I think he just wants one more. And she wants one more,” the KKW beauty founder says in the clip. “I mean, it’s, like, Scott has a girlfriend, Kourtney has a boyfriend, we get it, so they don’t even have to have sex. It can be like IVF.”
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The reality star shared a snap of herself with Disick, Mason and Penelope while on vacation with her family in Bali in November 2018. A source told Us at the time that she had decided to invite him so they could spend time as a family,” adding, “Coparenting couldn’t go better.”
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The exes showed they could play nice when they headed to dinner together … with Disick's paramour, Richie.
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Kourtney expressed gratitude for her baby daddy on Instagram for Thanksgiving. “I woke up this morning in bed with my children, in the same house as my sisters (minus @khloekardashian), my brothers, the father of my kids, my mommy, my grandma, my nieces and nephew. I feel beyond grateful,” she wrote.
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Kourtney and Disick hit their coparenting stride in 2018, when the former Dash owner shared a snap of her former flame on a bed with daughter Penelope on his lap as Kourtney strikes a sexy pose.
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Disick opened up to Us about his relationship with Kourtney during a joint interview with Khloé in June 2019.
“Just because their mother and I couldn’t make it as a perfect, romantic couple shouldn’t have anything to do with the kids,” he said. “They don’t deserve our mistakes, so we figured out a way. We still need to be as honest and as good to each other as if we were together. Let’s raise these children together and that’s it.”
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Richie made her KUWTK debut in October 2019 on a ski trip with Kourtney and Disick.
“You’re a lot more sophisticated with me when Kourtney’s around,” Richie quipped in the episode.
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Disick made headlines in April 2020 when an eagle-eyed fan account caught him “liking” old photos of him and Kourtney. Earlier that month, Kendall accused Kourtney of never fully dealing with the aftermath of her split from Disick on an episode of KUWTK.
“I think Kourtney, for a very long time, has felt really misunderstood and a lot of people feel like she’s being rude, but I know she means well,” Disick replied on the show. “And you just gotta see that through her and it’s kind of hard sometimes. But I do know that she wants to be on good terms with everybody. It just doesn’t always come out that way.”
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Kourtney posted a sweet Father’s Day tribute for Disick via Instagram, sharing a photo of the former pair posing with their three kids. “Happy Father’s Day,” she wrote. “Thankful for you and these three special ones.”
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The Poosh founder posted photos of the exes from their time at Kim’s private island 40th birthday bash. “selfie selfie,” she captioned the cute pics.
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