The 411: The Evolution Of Kourtney Kardashian And Scott Disick’s Tumultuous Relationship

By Isabel K July 10, 2022

Thanks to Keeping Up with the Kardashians, we all know about Kourtney and Scott Disick‘s tumultuous relationship. From what seems like endless fights to breakups, make-ups, and pregnancies, there is a lot of history between these two that would make anyone’s head spin. 

The reality tv show premiered in 2007, and the audience was introduced to several family members, including Kourtney Kardashian and her boyfriend, Scott Disick. Their relationship has been filled with many highs and lows that can be hard to keep up with. 

But don’t worry, we got you covered. Whether you were a fan of this couple or happy they’re not together anymore, here is a complete timeline of Kourtney and Scott’s relationship since 2006.

1. Kourtney on Keeping Up With The Kardashians

Kourtney Kardashian is the oldest sister in the Kardashian-Jenner clan. She went to college and studied Theater Arts and Spanish at the University of Arizona. When she was young, her mother, Kris Jenner, split from her father, Robert Kardashian, and married Olympic medalist Bruce Jenner.

Image Source: s_bukley / Shutterstock

While Kourtney dabbled in reality TV before Keeping Up with the Kardashians, she didn’t become really popular until she and her family starred in the E! reality show. She is now a published author and mother and has launched several clothing stores over the years. She also runs a blog called Poosh which she started in 2019. 

2. Keeping Up with Scott Disick

Scott Disick owes all his fame and money to the Keeping Up with the Kardashians reality show. While his parents were well off, Scott became famous for being Kourtney’s boyfriend when the reality show premiered in 2007. Scott has often bragged about his upbringing, saying he used to go to school in a limousine daily.

Image Source: Scott Disick / Instagram

It’s not surprising because he was the only child of Jeffrey and Bonnie Disick. His parents adored him and gave him everything he wanted while attending a private school in the Hamptons. Scott’s parents were a huge part of his life, making a couple of appearances on the show. 

3. Scott and Kourtney Meet at a Party

The relationship between Kourtney and Scott Disick started at a party in 2006. This was when Kourtney and Scott met at a Joe Francis party. Joe Francis was the founder of Girls Gone Wild and, at one point in time, also dated Kourtney Kardashian. They must’ve ended things well for Kourtney to be invited to his party.

Image Source: Scott Disick / Instagram

Joe even takes credit for introducing Kourtney to Scott at this party. Although Kourtney would later admit that she didn’t like Scott the first time they met, he definitely left an impression. Kourtney says she didn’t like him because he was an unemployed New Yorker and very annoying that night.

4. They almost got married in 2007

In 2007, this couple ran into one of their first hurdles. A pregnancy scare. During their first year of dating, the sisters were about to go on a Las Vegas trip when Khloe pushed Kourtney to take a pregnancy test. While it turned out that Kourtney wasn’t pregnant, it definitely made her think of the possibility of starting a family with Scott.

Image Source: Kourtney Kardashian Barker / Instagram

When she asked Scott about eloping and getting married in Vegas, he was down for the plan. Even though he knew she was a little drunk. Unfortunately, Kris Jenner would convince her daughter the following day about the importance of having family members around for such an important occasion. And the wedding was canceled.

5. Going Their Separate Ways

By the time the second season of Keeping Up with the Kardashians was airing, their relationship had become even more dramatic. At the beginning of the season, Kourtney finds a series of text messages that led her to believe that Scott is cheating. While Scott denied ever cheating on Kourtney, it led to their first breakup.

Image Source: Scott Disick / Instagram

Kourtney called it quits and left for Cabo San Lucas with the other Kardashian sisters. Although she was still holding onto hope for a while, she became scared that Scott was still cheating and decided to really call it quits and stay single to think about things clearly. By this time, they were already filming Khloe and Kourtney Take Miami in 2009. 

6. Making Up in Miami

The split between Kourtney and Scott Disick didn’t last long. After six months of being single, Scott reached out to Kourtney, but she didn’t answer his call. During an episode of Khloe and Kourtney Take Miami, Scott decided to make a surprise appearance at her party hosted by Scott Storch.

Image Source: Kourtney Kardashian Barker on Instagram

While Kourtney knew she was set up, she was happy to see Scott and was trying to keep her composure. Kourtney eventually agreed to dinner with Scott a few days later and even to a concert where they were seen making out. One thing led to another, and Kourtney ended up in Scott’s hotel room.

7. Kourtney Kardashian’s First Pregnancy 

While Kourtney was still deciding whether or not to get back together with Scott Disick, she had another surprise coming. She was pregnant with his child. She revealed years later that she had forgotten to take her birth control pills after she hooked up with Scott in Miami.

Image credits: Chris Wolf/FilmMagic

While she was not prepared at first, Kourtney immediately fell in love with motherhood. On multiple episodes of Kourtney and Khloe Take Miami, a number of pregnancy tests confirmed that Kourtney was pregnant. She and Scott decided to keep the baby after a trip to the doctor.

8. The Couple Welcomed Their First Child in 2009. 

In 2009 Courtney and Scott announced that they were expecting their first child together in December. Speaking to E-News, she said, “A boy is definitely needed in this family! Scott and I are thrilled to add a little boy to the bunch.”

Image Source: E! Online

Mason was born on December 14th, 2009. He weighed 7 lbs. 6 oz. In the season four finale of Keeping Up with the Kardashians, audiences were able to witness Mason Dash Disick’s birth. Kourtney even pulled Mason out herself during his birth. What a strong woman!

9. Scott’s Substance Abuse Issues Affected Their Relationship

Sadly, the couple didn’t enjoy being new parents together for long. Soon after Mason was born, Scott’s partying and anger bursts became more uncontrollable. Courtney would return home to find empty alcohol bottles and the smell of marijuana everywhere.

Image Source: Scott Disick / Instagram

During this time, Courtney and Scott had moved with Mason to Miami for a year. But this decision only made Scott partying and drug use worse. They also got into a physical altercation, so Scott decided to seek help for his problems and go to rehab. Eventually, Courtney took him back because he vowed to change his behavior.

They Almost Got Engaged in 2011

Kourtney and Scott Disick’s relationship continued to play out on the Keeping Up With the Kardashians spinoffs. This time it was on an episode of Kourtney and Kim Take New York. Their on-and-off relationship almost turned into an engagement in 2011.

Image Source: Kourtney Kardashian Barker / Instagram

In an episode of this spinoff, Scott goes shopping for an engagement ring. He was joined by Kim during the shopping trip and explained to her that he was at a point in his life where he was ready to buy an engagement ring instead of the usual earrings and a necklace. Unfortunately, Kourtney didn’t want to mess things up at that moment, so she refused his proposal.

The Birth of Penelope Disick in 2012

Despite not getting married, the couple was still enjoying their relationship. The two decided to have another child together. Kourtney announced they were pregnant with her second child in November 2011. Disick told US Weekly that although they weren’t trying. If it’s meant to be, it’ll be.

Image Source: Scott Disick on Instagram

Penelope Disick was born on July 8, 2012. Like her first pregnancy with Mason, Kourtney also helped deliver her daughter by pulling her out during the final moments of hard labor. Penelope’s birth was also televised in an episode of Keeping up with the Kardashians season seven.

12. The Passing of Scott’s Parents

Losing a parent is something difficult for anyone to go through. It’s even harder when you lose both parents within the same year. That’s what happened to Scott Disick. Bonnie Disick, his mother, died in 2013 after suffering from a long illness.

Image Source: Scott Disick / Instagram

Unfortunately, Scott’s father, Jeffrey, also passed away months later in 2014. Being an only child, Scott was left with no family, but the Kardashians took him in as one of their own. His parents’ death affected most of his personal relationships and only worsened his struggles with substance abuse.

13. Welcoming Reign Aston Disick in 2014

Two years after the birth of Penelope, Kourtney  Kardashian announced that she was pregnant with her third child with Scott Disick. During this time, Kourtney was filming Kourtney and Khloe Take the Hamptons, and Scott had returned to his hard-partying habits.

Image Source: Kourtney Kardashian Barker / Instagram

When Kourtney told Scott the news of her pregnancy during the ninth season of Keeping Up with the Kardashians, it was clear to everyone, including the viewers, that they hadn’t planned for another baby. Scott said that he couldn’t handle the responsibility of another child. Reign Disick was born on December 14, 2014.

Their Final Split in 2015

After being called out for his party binges and hooking up with an ex-girlfriend, Kourtney finally ended their relationship for the third time. Their relationship now turned into something completely different because they still had kids to raise together.

Image Source: Kourtney Kardashian Barker / Instagram

The ex-girlfriend in question was Chloe Bartoli. They hadn’t dated or been seen together for over nine years. So when Kourtney finds out about Scott hanging out with his ex-girlfriend, she asks Scott to move out of their house so she can focus on caring for her young kids. 

15. Co-Parenting Their Three Children

After the breakup, Kris Jenner said that Kourtney was hanging in there and focusing on her family. Their relationship now enters a new phase As they begin the journey to co-parent and be there for their kids. This meant they were spending a lot of time together around the kids. 

Image Source: Kourtney Kardashian Barker / Instagram

Raising three children is not an easy job. Especially when you are a famous reality TV star with paparazzi following you everywhere. Kourtney said the kids enjoyed these outings to the zoo with both parents, but the paparazzi always made it uncomfortable for them to enjoy themselves.

16. Trying to Make it Work Again 

While they were still trying to get the hang of co-parenting, Scott began changing his behavior, and Kourtney noticed. They smoked together for one last time, according to a Source close to the family. The source said, “ They are back together and giving the relationship a try again.” 

Image Source: Kourtney Kardashian Barker / Instagram

The insider added, “ Scott mellowed out a lot and hasn’t been partying.” Scott’s hard-partying and alcohol use were one of the major problems Kourtney had to deal with in their relationship. Well, there might’ve been some hope, but the couple realized that it wasn’t going to work.

17. Kourtney and Justin Beiber

After finally calling it quits, rumors started going around that Kourtney Kardashian was dating singer Justin Bieber. At this time, Scott was constantly photographed hanging out with very young women at parties and clubs. Kourtney had decided to move on with her life, too.

Image Source: Kourtney Kardashian Barker / Instagram

Kourtney, 36, was frequently spotted hanging out with a 21-year-old singer. Scott, however, made it all about himself, saying that she was only hanging out with the singer to make him jealous. He wasn’t too thrilled about who his ex was going out with. Was it because he was younger or richer than him?

18. Getting the Hang of Coparenting

In 2016, despite the ups and downs in their personal relationship, the couple was determined to be there for their children. They didn’t want them to miss out on having a ‘family.’ Kourtney said to a magazine, “ I find co-parenting easy. Scott and I communicate all the time.”

Image Source: Kourtney Kardashian Barker / Instagram

The reality tv star added, “You have to keep discussing what’s going on because the children grow old, and the rules need to be renegotiated.” Raising three kids is challenging, especially in the public eye. They obviously had to discuss a lot of aspects regarding their children’s future and education.

19. Scott Seeks Help

In order to be good at co-parenting, Scott knew that he had to change his behavior and lifestyle. Scott spent a lot of time in rehab and therapy over the years. While he was clean for a while, he had a relapse and had to go back in 2014.

Image Source: Scott Disick / Instagram

This was a short while after filming Kourtney and Khloe Take The Hamptons. In 2015, Scott went to rehab again in Costa Rica to deal with his substance abuse issues. Although he only stayed there a month, he was back in rehab after splitting with Kourtney. Only this time, it was in Florida. 

20. Scotts Numerous Flings

While these two seem to be experts at co-parenting, their personal relationships were more complicated for them to handle. During an episode of Keeping Up with the Kardashians, the sisters barge into Scott’s hotel room only to find a woman hiding in the bathroom while they are on vacation.

Image Source: Scott Disick / Instagram

And this wasn’t the only woman he was linked to at the time. Scott was also rumored to be dating actress Bella Thorne, with whom he went to the Cannes Film Festival, Jessica Harris, Lina Sanberg, and Megan Blake. He seemed to be hooking up with a lot of young women after his breakup with Kourtney.

21. Kourtney and Scott get into Serious Relationships

After several casual hookups with younger people, Kourtney and Scott decided to take their other relationships seriously. Scott started dating model Sofia Richie, who is 14 years younger than him. She’s also the daughter of singer and songwriter Lionel Richie.

Image Source: Kourtney Kardashian Barker / Instagram

Kourtney also went on to date someone younger than her. In 2017 she started dating Algerian model Younes Bendjima who was also 14 years younger than her. Maybe the age difference is just a coincidence. But, they both knew what they were getting into since they were still co-parenting their three kids.

22. Co-Parenting on Vacations

In 2017, Kourtney seemed to confirm that their co-parenting was going well despite what the tabloids were reporting. During a family vacation, she took a picture with Scott and captioned it, “Mom and Dad back at it again with the co-parenting skills.”

Image Source: Kourtney Kardashian Barker / Instagram

It seems that things were going well enough during their family vacations. Being there for the children now is what is important for them, which is one thing they can agree on. This wasn’t going to be the last of their family vacations together, even though they were separated.

23. Relationship Boundaries

When new relationships start, they must have clear boundaries for them to work. Especially for this pair, because dating Scott is like dating the Kardashian family. Despite not being together with Kourtney, the Kardashian-Jenner clan still considers him a part of their family.

Image Source: Kourtney Kardashian Barker on Instagram

Communication is key in any relationship, especially when you’re co-parenting. During an episode of Keeping Up with the Kardashians in 2018, Kourtney decided to lay down some relationship rules. She asked Scott not to enter her room without permission. Scott completely agreed because he didn’t want to make Kourtney uncomfortable.

24. Going on Family Vacations. 

Despite having plenty of boundaries in place, the pair still went on family vacations together. If you’re a part of the Kardashian family, those vacations are too good to miss out on. In 2018, they all went on a family vacation to Mexico.

Image Source: Kourtney Kardashian Barker / Instagram

Sofia wasn’t left behind either. While it could have been awkward, it seems they’ve all adjusted to spending time together as a blended family. These two seemed to be the best co-parenting ambassadors. They also spent holidays like Thanksgiving together, as seen from their near-perfect Instagram photos.

25. Scotts Girlfriend on Vacation With the Family

Scott and Kourtney seem to be really mature about each other’s relationships. While going on vacation with your ex might seem weird to most people, they probably just want the kids to enjoy having both parents around. And Sofia didn’t mind at all.

Image Source: Cobra Team / BACKGRID

The three of them have been seen vacationing and dining together numerous times. But during an episode of Keeping Up with the Kardashians where Sophia made her debut, she revealed that Scott is more serious and mature when around Courtney Kardashian. Could that have been the first sign of trouble?

26. Scott and Sofia Still Going Strong

Despite the constant rumors of a nasty breakup between Scott and Sofia, by 2019, the couple was still going strong. According to sources close to the family, Sofia loved playing with Scott’s children and also loved taking vacations together.

Image Source: LRNYC / MEGA

After spending Scott’s 35th birthday in St. Barts, many people wondered whether they would settle down together soon. They even moved into a place together. Sofia clarified, though, that she was always around the kids with Scott and helped out when necessary so he could put all his attention on his children.

27. Scott’s View On Co-parenting

While we know how Kourtney feels about co-parenting, what about Scott? In 2019, he was asked about his current relationship with Kourtney Kardashian, and he had some things to clarify. He said, “Just because the mother and I couldn’t make it as a perfect romantic couple doesn’t have anything to do with the kids.”

Image Source: Kourtney Kardashian Barker / Instagram

These were some very wise words from the once immature Scott Disick. He also added that the kids didn’t deserve any of the parents’ mistakes, so they figured out a way, to be honest with each other while raising the kids, which is best for all parties involved.

28. Sofias Ultimatum to Scott

While things between Scott and Sofia seem to be going well in the public eye, it might not have been as rosy as we thought. Although the couple moved into their own place in Malibu, their relationship had reached its limit. They broke up in 2019.

Image Source: Scott Disick / Instagram

We might now know what caused the split. Scott claimed that Sofia was trying to push Kourtney out of his life. He says that Sofia issued him an ultimatum to choose between her and Kourtney Kardashian. Scott made it clear that the most important thing to him was his family and kids, including Kourtney Kardashian.

29. Family Dinners at Nobu

After splitting up with Sofia, Scotts started dining out more with the Kardashians and Jenners, especially Kourtney. One restaurant they liked to frequent was Nobu. Like normal, they also went on another family vacation with the other Kardashians for Scott’s 37th birthday.

Image Source: Kourtney Kardashian Barker / Instagram

Their friends and family would constantly ask about a possible reunion between them. They even posted pictures together, looking playful during Kim Kardashian’s 40th birthday. Those selfies got fans talking and speculating that the two were back together again.

30. A Possible Reunion?

While Kourtney and Scott didn’t confirm anything about their possible relationship, it didn’t stop their fans and family members from wishing for a possible reunion. In the summer of 2020, this former couple was staying at a Wyoming ranch with their kids.

Image Source: Kourtney Kardashian Barker / Instagram

Kourtney posted a photo holding a baby goat wearing an oversized flannel shirt. But it wasn’t just any flannel. It belonged to Scott. Scott even commented on her Instagram picture with “cute shirt,” leading many to speculate that something had happened, or maybe they just have a very friendly co-parenting dynamic.

31. Kourtney is Really Done

Over the years, many people have tried to convince Kourtney to give her relationship with Scott another chance. Including her mother, Kris Jenner. In an episode of Keeping Up with the Kardashians, Kris told Kourtney that she would love her daughter to grow old with someone, and it would be fabulous if it were the father of her kids.

Image Source: Kourtney Kardashian Barker on Instagram

Caitlyn Jenner, Kris’ then-husband, agreed. He said, “I would hope he can kinda get his act together.” But Kourtney found most of these suggestions annoying. During a confessional, she said that her whole family likes bringing up her and Scott getting back together. She just didn’t want it to keep being a topic of discussion.

32. The Baggage They Both Carry

For a segment of Kourtney’s lifestyle website to Poosh, she decided to have Scott appear to discuss the unique co-parenting relationship. According to the couple, they feel that they are a very strong parenting unit when it comes to raising their kids.

Image Source: Scott Disick / Instagram

Scott said, “I think other people just think if they were in that position, they couldn’t do it, and it’s not like the easiest thing for us. But the fact that we’ve tried and we made it work makes life that much better. I mean, I couldn’t imagine raising three children with somebody that I couldn’t speak to every day.“

33. Finding a Comfortable Routine For Their Family

With close to ten years of co-parenting under their belt, this couple has to do many things to keep the peace. Both Scott and Kourtney have talked about the importance of routine in the success of their co-parenting. The kids have the same routine no matter who’s house they sleep in.

Image Source: Kourtney Kardashian Barker / Instagram

Luckily both Scott and Kourtney live close to each other, and the kids are allowed to go to any of the houses they like. Scott said that he didn’t want his kids to feel pressured into choosing one home because of how they might do things differently.

34. Reflecting On Their Co-parenting Journey

Looking back at the relationship, Kourtney believes that she made the best decision for her and her kids. While talking to Andy Cohen after the end of Keeping Up With the Kardashians, she said that Scott’s substance abuse was the main reason they broke up in 2015.

Image Source: Scott Disick / Instagram

At the time, Courtney wasn’t even aware of his infidelity. Scott also admitted that some of the things he did were because he was not sober. Although he realized he was wrong, he thought it was normal at the time. But, he added that they would always be family.

Scotts New Flame

With the co-parenting going smoothly, Scott decided to start dating again. In 2021, he started dating 19-year-old Amelia Gray Hamlin. This was controversial because, at the time, Scott was 38 years old. Amelia is the daughter of reality TV stars Lisa Rinna and Harry Hamlin.

/Image Source: Scott Disick Instagram

This relationship was surrounded by many controversies, with many people pointing out the considerable age gap. They met at Kendall Jenner’s Halloween party and started flirting right after. When Amelia asked about the relationship, she said, “People can embrace themselves however they feel fit for them at that moment in time.”

36. Kourtney and Travis Backer

Scott wasn’t the only one moving on with someone new. Kourtney started dating former Blink 182 drummer Travis Barker. The two had been longtime friends, and their kids also knew and spent time with each other. In April 2021, their relationship seemed like a light-hearted romance.

Image Source: Travis Barker / Instagram

Travis has also been in his own on-and-off relationship. He was married to Shanna Moakler, and they even starred in a reality TV show known as Meet the Barkers– which lasted for only two seasons. The ex-couple divorced in 2008 and co-parented their kids together as well.

37. Scotts Jealousy Starts Showing

Things seem to be going well between Kourtney and Travis, and rumors had it that they had entered into a serious relationship. Scott, now single, admitted to being jealous of Kourtney’s new relationship with Travis Barker. He was so jealous that he ended up causing more drama.

Image Source: Keeping up with the Kardashians / YouTube

In 2021, it was revealed that Scott had messaged Kourtney‘s ex-boyfriend Younes Bedndjima on Instagram. Scott had earlier bashed Younes when he was dating Kourtney, so Younes leaked his message to the world. Scott had sent him a message complaining about Kourtney’s PDA with Travis.

38. Kourtney’s Engagement

Despite what most people thought, Kourtney and Travis were serious with each other. This was taken seriously when Kourtney got Travis to get back on a plane after not flying for 13 years following a devastating plane crash. To many, this was the most serious relationship she’s ever been in.

Image Source: Kourtney Kardashian Barker / Instagram

In October 2021, Travis proposed to Kourtney Kardashian with a beautiful surprise next to the beach, and they got engaged. Kris helped set up the surprise, but sadly, Kourtney’s kids couldn’t make it. Scott was jealous and said that it was hard for him to be around the newly engaged couple.

39. Adding Another Child to the mix?

After Keeping Up With the Kardashians ended, the family moved to Hulu with a new Reality TV show called The Kardashians. On the show, Kourtney and Travis are trying to conceive a child together, which Scott isn’t so happy about.

Image Source: Kourtney Kardashian Barker / Instagram

According to Us Weekly, Scott wished things were different and said that Kourtney was the one that got away. Although he added that his kids are the ones who make him the happiest, it’s clear he has always been jealous of Kourtney’s relationships with others. But it was too late now.

40. Kourtney and Travis Get Married

In April 2022, Kourtney and Travis got married in a surprise Las Vegas ceremony just like she always wanted. Though the ceremony happened with an Elvis Presley impersonator without a license, the two were serious and set a date for the real thing.

Image Source: Kourtney Kardashian Barker / Instagram

They made things official in a beautiful wedding ceremony at a castle in Portofino, Italy. The wedding was attended by their close family and friends and sponsored by Dolce and Gabbana. Scott wasn’t emotionally ready to see her ex get married. Their new family just got bigger, but Scott has yet to speak on the wedding of the year.