An Inside Look at Kourtney and Scott's Relationship


| LAST UPDATE 03/31/2021

By Genevieve Scott

"The idea of having my family together is amazing... but it's not the way things ended up," Kourtney revealed. But where'd it all go wrong? Hang on while we walk you through one of America's most talked-about couples over the years.

Kourtney & Scott

Kourtney and Scott first crossed paths 15 years ago. Since then? We've seen breakups, makeups and endless tears shed. Their complicated romance has been anything but easy. And it's left the online world running wild.

Scott Disick, Kourtney KardashianScott Disick, Kourtney Kardashian
David Becker/WireImage via Getty Images

From falling in love to falling apart - to everything in between - their journey as co-parents has certainly been one for the books. Let's look back at their unforgettable time in Hollywood over the years, and everything that landed them in the position they are in now.

The Moment they First Met

Back in 2006, a 28-year-old Kourtney Kardashian was partying her way through Mexico when she first met Scott Disick. Little did she know everything was about to change. But don't think it was love at first sight. As a matter of fact? It was anything but.

Scott, Kourtney Kardashian, ScandalScott, Kourtney Kardashian, Scandal
Instagram via @kourtneykardash

"I liked her, but she wanted nothing to do with me," Disick recalled of the moment the two crossed paths. How did Kourt see it? "I just thought he was so annoying," she revealed. "He was 4 years younger, he lived in NY, and he didn't have a job." Of course, those feelings didn't last long.

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They Made Their Couple's Debut in KUWTK

Whatever the story may have been, by the time 2007 came rolling around, nothing was the same. Kourtney, along with her sisters, had officially made her debut on our TV screens. But that wasn't all she did. She also introduced us to a special somebody.

Kourtney Kardashian, Scott, DramaKourtney Kardashian, Scott, Drama
Polk Imaging/FilmMagic via Getty Images

Her boyfriend, Scott. Yep, the very same 24-year-old living in New York without a job to his name. But none of that mattered anymore. Kourtney was crushing, hard. And in only a matter of time, their love story would truly take off. But that didn't mean it'd be easy.

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Trouble in Paradise

It's hard to think of a time where these two weren't somehow involved in each other's lives. But by 2008? Kourt's mind was made up: She no longer wanted anything to do with Scott. The season 2 premiere of KUWTK had just aired. And with that, came a whole lot of dirty laundry.

Scott Disick, Kourtney, DramaScott Disick, Kourtney, Drama
Ray Tamarra via Getty Images

Scott had been seeing another woman. Or at least that's what Kourtney swore, as we watched her toss his phone and kick him to the curb. Nonetheless, fate had other plans for the two of them; Which meant as hard as she may have tried, Kourt's path soon pointed her in her ex's direction.

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Kourtney Got Pregnant

"It's the best thing that happened to me," Kourt recalled of the moment everything suddenly changed. She was pregnant; Something neither she nor Scott had ever planned for. But what did she know? That she was going to make it work - for their baby's sake, at the very least.

Kourtney Kardashian Pregnant Kourtney Kardashian Pregnant
BuzzFoto:FilmMagic via Getty Images

And that's exactly what they did. After endless months apart, the former exes came together as they braced their latest chapter: Parenthood. Sure, her sisters were skeptical of the man she now wanted to raise a child with; But could we blame them? It all happened so fast.

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Welcoming Mason Disick

Sure enough, on December 14, 2009, proud parents Kourtney and Scott welcomed Mason Dash Disick. "It's such a spiritual thing," Kardashian gushed of her latest chapter; One of the happiest moments of her life - even if it left her feeling completely lost.

Mason, Scott, Kourtney KardashianMason, Scott, Kourtney Kardashian
Jean Baptiste Lacroix/WireImage via Getty Images

"I remember coming home from the hospital and having no idea what we were doing," Kardashian explained of their new reality. Nonetheless, the new parents were seemingly over the moon; Happier than ever; Something that wouldn't last long, as they'd soon find out.

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Scott's Partying Ways

Unfortunately, by 2010? Life for the growing family suddenly took a dark turn: Scott was heading down the wrong path - a dark one - and it wasn't long before people took notice; Including, of course, Kourtney. "I can't do this anymore," the emotional mom admitted on our TV screens.

Scott Disick, Party, ScandalScott Disick, Party, Scandal
Denise Truscello/ Contributor via Getty Images

Sure enough, she was right: Their documented trip to Miami Beach had gone sour, fast. And with Scott's partying ways reaching an all-time high? Kourt had finally had enough. And so, she packed her bags and said goodbye as she hopped on a plane to L.A. - solo.

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He Tried Proposing to Kourtney

As we already know, though, their story was far from over. In fact, it was just getting started. By 2011, the on-again-off-again couple was officially back on - and seemingly better than ever. In fact, Scott was ready to take the next step in their relationship. Sadly, it didn't pan out the way he planned.

Kourtney, Scott, Marriage, RumorsKourtney, Scott, Marriage, Rumors
David Becker/WireImage via Getty Images

The smitten star's grand plans to get down on one knee were almost instantly squashed. "Why mess it up?" Kardashian asked him. "I just feel like right now, I'm happy with the way things are." Little did she know, her euphoria was about to reach new heights.

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They Welcomed Penelope

"It wasn't like we weren't trying," Scott revealed in 2012 after officially becoming a family of four. "We kind of just said, 'If it's meant to be, it'll be.'" Sure enough, on July 8, 2012, Kourtney and Scott welcomed a beautiful baby girl into the world: Penelope Scotland Disick.

Kourtney, Scott, Penelope, SecretsKourtney, Scott, Penelope, Secrets
JB Lacroix/WireImage via Getty Images

Much like her older brother, we'd soon come to know baby Disick all too well. But long before Mason and Penelope joined mom and dad on our screens, there were other changes inside the famous household. Only this time, they'd bring devastation like never before.

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Heartbreak in the Disick Family

In the span of just three months, Scott Disick's reality took him from a proud, new parent to parentless; A devastating pill to swallow. And it hit him, hard. "Losing my parents is not an easy subject for me to talk about… to remember them and think about them," the emotional star revealed.

Scott Disick, Parents, ScandalScott Disick, Parents, Scandal
Instagram via @letthelordbewithyou

In October of 2013, the reality star said bye to his mother, Bonnie. Her chronic illness had taken its toll; But just weeks later, he was met with more heartbreak. His father, Jeff had also passed. "It's definitely not easy, the fact that I don't have my parents here. I miss them a lot."

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Welcoming Baby #3 Overwhelmed Scott

After Scott's reality left him in sudden mourning, he was soon struck with another surprise: Kourtney was pregnant, again. Only this time around? The reality star didn't welcome the news with open arms. He was simply drained, in every which way imaginable.

Scott Disick, Reign, ViralScott Disick, Reign, Viral
Instagram via @letthelordbewithyou

"I barely feel like I can take care of myself. I'm hanging on by a string here," he revealed. Nonetheless, on December 14, 2014, the distraught star became a father of three as news spread of their latest arrival: Reign Aston Disick; A blessing in disguise, as he'd eventually find out.

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He Sought Professional Help

There was no denying it: Everything happened so fast; The highs, the lows, the constant changing going on around him. And unfortunately for Scott, it soon became too much to bear. By 2014, the lost and confused star was seemingly headed down a slippery slope.

Scott Disick, Viral, RehabScott Disick, Viral, Rehab
Instagram via @letthelordbewithyou

"I [messed] up. I made the worst decision I could have ever made in my life," Disick revealed of the moment he realized he needed professional help. His struggle with substance abuse had officially hijacked his life - and he was ready to take it back. Or at least try to.

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He Was Caught With a Mystery Woman

By spring of 2015? Everything seemed to finally fall into place. Scott had been released from the rehabilitation facility. He and Kourt were seemingly patching things up. Of course, though, not everything was as it seemed. At least where paparazzi were concerned.

Scott Disick, Cannes, CheatingScott Disick, Cannes, Cheating
Bauer-Griffin/GC Images via Getty Images

Pictures began plastering our feeds of Scott vacationing in the South of France; The only problem? The woman captured by Disick's side was not his girlfriend. It was his ex, Chloe Bartoli. Where was Kourt? Back in L.A. looking after their children. Sure enough, it wasn't long before Kardashian called it quits, for good this time.

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Rumors of Kourtney and Justin Bieber Began

Sure, it seems almost odd to picture Justin with anyone other than Hailey. But back in 2015, as news broke of Kourt and Scott's split, so did other discoveries. Of course, we're talking about Kardashian's alleged relationship with the Baby hitmaker. Remember that?

Justin Bieber, Kourtney KardashianJustin Bieber, Kourtney Kardashian
Instagram via @justinbieber

While the two never confirmed the buzzing rumors, they sure gave fans reason to believe it to be so. From late-night rendezvous to loved-up selfies, their time together was nothing short of eventful. And you can bet people had questions, lots of them.

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Kourtney Became Official With Younes

Sure enough, our questions were finally answered by 2016; The moment Kourt stepped out with a new man: 23-year-old boxer, Younes Bendjima; But what we didn't know at the time, was that it was far from a summer fling. Their relationship would last almost 2 years; Something skeptics never saw coming.

Younes, Kourtney Kardashian, ViralYounes, Kourtney Kardashian, Viral
Bertrand Rindoff Petroff via Getty Images

Including, of course, Scott Disick. With whispers of Kourt's new relationship plastering headlines, the star was not happy. Or at least that's how fans saw it, after his latest deed found its way onto our screens. And you can bet it left viewers with lots to say...

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Scott Snuck a Woman onto a Family Vacation

"Let's cut the bull," we watched an angry Kim shout, as she confronted Scott. What happened? He had snuck a mystery woman - "Chelsea" - onto their family vacation in Costa Rica. "Someone with any kind of integrity would never do something like that," Kris fired.

Scott Disick, Costa RicaScott Disick, Costa Rica
Keeping Up With the Kardashians (2017) YouTube via E! Entertainment

Of course, it wasn't long before Scott took to our screen to set the story straight himself. How did he explain it? "Obviously, we're both trying to move on," Disick muttered. "So I'm trying to do everything I can do to not think about her."

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Scott Tried to Make Kourtney Jealous

Sure enough, in 2017, a healing Scott had finally gotten his wish: He had moved on. He was now dating actress Bella Thorne. Or at least that's how it seemed, as the two jetted off to Cannes together. But, as we now know, his latest endeavor meant absolutely nothing. He was out for revenge.

Bella Thorne, Scott DisickBella Thorne, Scott Disick
starzfly/Bauer-Griffin/GC Images via Getty Images

"He was like, 'Yeah, I'm doing it to make Kourtney mad,'" Kim revealed of the words she was met with upon confronting Disick. "There's a lot of anger. Like, wow, it's really real - us not being together," Scott himself soon added of the ongoing heartbreak.

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He Began Dating Sofia Richie

We already know how crushed Scott's former relationship had left him. But by the time winter came rolling around? Everything had suddenly changed. Scott had moved on; This time, with none other than Sofia Richie. And he'd be doing things differently this time around.

Scott, Sofia Richie, KourtneyScott, Sofia Richie, Kourtney
Denise Truscello/Getty Images for Wynn Nightlife

From jet-setting around the globe to hitting the red-carpet, Scott and Sofia were seemingly unstoppable. And after her debut on Keeping Up With the Kardashians? To the naked eye, the new couple seemed happier than ever; Drama free - for now, at least.

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Scott & Kourtney Co-Parent

Of course, though, there was still an elephant in the room: Scott's former relationship with Kourtney. Sure, they had both moved on, seemingly better than ever; But they still had children to co-parent. And, well, we couldn't help but wonder: Where would that leave them?

Scott Disick, Kourtney, FamilyScott Disick, Kourtney, Family
Instagram via @kourtneykardash

"There's obviously some boundaries that we both need to respect," Disick confronted Kourtney on an episode of KUWTK. "I don't want you to be uncomfortable." 3 kids and endless breakups later, the two had finally come to an understanding; One that'd soon lead to a shocking announcement...

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Scott Wanted a Fourth Kid

"So, Scott just texted me that he wants to have another baby with Kourtney," Kim gushed of the events that soon transpired. There was no going back now. The rumors had officially run wild. "I think he just wants one more. And she wants one more," the SKIMS mogul explained.

Reign, Scott, Kourtney, RumorsReign, Scott, Kourtney, Rumors
Instagram via @letthelordbewithyou

But what about their current relationships? How would Sofia and Younes take the news? "I mean, it's, like, Scott has a girlfriend, Kourtney has a boyfriend, we get it," Kardashian continued; But according to Kim? That didn't have to mean anything. "It can be like IVF."

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Kourtney Was Upset With Scott & Sofia

We already know that Scott and Kourt's family dynamic is... complicated. But where are they supposed to draw the line? Unfortunately, if you ask Kourt, her ex-boyfriend stepped over it ages ago: The moment he introduced their children to his latest girlfriend.

Sofia, Scott, Kourtney, FightSofia, Scott, Kourtney, Fight
Instagram via @letthelordbewithyou

"It's called giving someone a heads up... giving someone the respect," Kourtney shaded. After over a year of dating, Scott had brought Sofia around the kids. And Kourt was not having it. "You're not following through with the things that you say you're gonna do... and I'm not okay with it."

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Sofia Began Questioning Scott & Kourt's Relationship

As we already know, Sofia and Scott's troubles were just getting started. And as the months continued to pass, Richie couldn't shake the feeling that something was wrong. "You're a lot more sophisticated with me when Kourtney is around," she finally revealed. "You turn into a 5-year-old when it's just us."

Sofia Richie, Scott, FightSofia Richie, Scott, Fight
JB Lacroix/GC Images via Getty Images

From complicated exes to to all of the rumors that soon followed, the couple had certainly been put to the test. But by 2020? They were officially done. After 3+ years of dating, Scott and Sofia had called it quits. And this time, there would be no reconciliations.

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Scott Admitted to Having Trust Issues

Over the years, Scott Disick was put through a lot - until suddenly, he couldn't take it any longer. During the summer of 2020, the star checked himself into a rehabilitation facility. Only this time, his cry for help was met with a brutal betrayal. And it stung.

Scott Disick, Rehab, ScandalScott Disick, Rehab, Scandal
Instagram via @letthelordbewithyou

"There couldn't have been a bigger betrayal," an emotional Disick revealed. What happened? "[Someone] leaked me being there to the press," he explained. And with that, Scott packed his bags and left the Colorado facility - mere days after checking in. "I don't trust anybody."

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Scott & Kourtney Hint At a Reconciliation

Through everything Scott had been through, there was one face almost always by his side; Someone who'd stuck it out even in the darkest of hours: Kourtney. And as her ex struggled in the spotlight, you can bet she was there. "Thankful for you," she soon wrote on Instagram, alongside a snap of their family.

Scott, Kourtney Kardashian, ReuniteScott, Kourtney Kardashian, Reunite
Instagram via @kourtneykardash

Of course, it wasn't long before her latest post sent the online world buzzing. Are Kourtney and Scott finally getting back together? people wondered. From trips to the grocery store to Nobu dinners, the signs were certainly there. At least as far as fans were concerned.

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Scott Became Official With Amelia Gray

As the story goes, though, all of those whispers were finally silenced by February. Scott Disick had a new lady in his life: 19-year-old model Amelia Gray Hamlin. And after months of speculation? He was finally ready to go public with their relationship.

Scott, Amelia Gray, KourtneyScott, Amelia Gray, Kourtney
MEGA/GC Images via Getty Images

"Why so serious?" he joked, alongside a snap of them vacationing in Miami. The timing was anything but random. What better way to make their couple's debut than on Valentine's Day - the most romantic time of the year? Only his latest deed left us with more answers than questions.

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He Admitted He Loves Kourtney

Back in December, mere weeks before he'd introduced us to Amelia Gray? Scott had "introduced" us to somebody else: "The best baby-maker in town," as Disick himself put it. That's right. Any guesses who he was referring to? Kourtney Kardashian, of course.

Scott, Kourtney, Instagram, RumorsScott, Kourtney, Instagram, Rumors
Instagram via @letthelordbewithyou

"Thank you, [Kourtney], for being the best baby maker in town," Scott gushed, alongside a sweet snap of his little ones. "I couldn't have asked for a better person in the world to have these amazing children with." Were we missing something? "I love you and our family more than anything in the world."

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Kourtney Was "Better Off" Without Him

From gushing about his beloved baby maker to going public with a new girl, fans were... confused. And it appears they weren't the only ones. On February 13th, as news broke of Scott's latest adventures, Kourt had lots to say. Then again, it's more what she did than said, that left us scrambling.

Kourtney, Scott, Instagram, CommentsKourtney, Scott, Instagram, Comments
Instagram via @kourtneykardash

After Miley Cyrus posted a snap on Instagram, fans couldn't help but notice Kourt had 'liked' and commented a heart on the post. As for what the message read? "You're better off without him if he's gonna choose her over you. He obviously has no taste." Was she implying what we think she was implying?

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Rumors of Kourtney & Travis Barker Began

Whatever the truth behind the swirling rumors may have been, everything changed - mere days later; The moment we came to meet Kourt's alleged new man: Travis Barker; Otherwise known as the 45-year-old drummer for Blink-182. And her family friend... until now.

Travis Barker, Kourtney, InstagramTravis Barker, Kourtney, Instagram
Instagram via @kourtneykardash

It started with the two sharing the same story of a fireplace on the 'gram. Then, Kourt's latest post: A cryptic snap of the two of them holding hands. If you asked fans? There was no denying it. The signs were all there: Kourtney Kardashian had officially moved on.

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KUWTK Ignited New Rumors of Kourtney & Scott

On paper, our story should end here: Kourtney and Scott finally move on, after building a happy medium as co-parents. Only that's not where this story ends. On February 11, 2021, Keeping Up With the Kardashians dropped a teaser for their upcoming season. And it left us questioning everything we thought we knew.

Kourtney, Scott, Kim, ReunionKourtney, Scott, Kim, Reunion
Instagram via @kourtneykardash

"You guys. I came over here in the morning… and I saw Kourtney and Scott asleep together on the couch," Kim gushed to her sisters in shocking new footage. Could it be? Had the couple secretly reunited behind closed doors? "Like, what's the harm in trying?" Khloe wondered.

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What Next?

Well, what now? While the status of their current relationship is seemingly unknown, if there's one thing we do know? It's this: "I don't know what the definition of soulmate is, but Scott and I? We're going to be in each other's lives forever," Kourt revealed. "We're soulmates in a sense…"

Scott Disick, Kourtney, RumorsScott Disick, Kourtney, Rumors
Instagram via @kourtneykardash

Sure, they've had their fair share of road bumps along the way. But throughout their journey on our screens? They've made memories they'll cherish forever; A past to look back on and smile about. As for what lays ahead? "To me, it's in God's hands. If it's meant to be, then things will line up."

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