The Complete Timeline Of Kourtney Kardashian And Scott Disick's Relationship

When "Keeping Up with the Kardashians" premiered in 2007, viewers previously unfamiliar with the Kardashians and Jenners met the whole family — and a variety of people who were important in their lives. Among those featured in the series were the eldest Kardashian sister, Kourtney Kardashian, and her boyfriend Scott Disick. In the 20 seasons since the show premiered, we've been privy to the ups and downs of Kardashian and Disick's relationship, including what seems like every fight, breakup, make up, pregnancy, childbirth, and more. Even for the most well-versed Kardashian fan, it's enough to make your head spin! 

If you have a hard time keeping the timeline of their roller coaster relationship straight, you're not alone, but we're here for you. Whether you loved them as a couple through thick and thin or rejoiced every time they split, here's the complete timeline of Kourtney Kardashian and Scott Disick's relationship over the years.

The Kourtney Kardashian and Scott Disick relationship timeline all started in 2006, when Kardashian and Disick both attended a party hosted by "Girls Gone Wild" founder Joe Francis. According to Complex, Kardashian and Francis had previously dated, but the pair clearly remained friendly enough for Kardashian to be invited to party in another country with the controversial entrepreneur. 

Francis told InTouch in 2014 that he introduced the pair at his house in Mexico. "Scott came as the guest as a friend of mine, and they met in my master bedroom," he revealed. While Francis later alleged that Kardashian initially hated Disick, the beginning of their long and turbulent relationship was set into motion that night.

Kardashian seemingly confirmed the story of how she and Disick met when she posted a Flashback Friday group photo on Instagram that included her, Disick, and Francis, among others, and shared in the photo's caption that it was taken the night she and Disick first met.

From the very beginning, Kourtney Kardashian and Scott Disick's relationship moved at a fever pitch. In the very first season of "Keeping Up with the Kardashians" in 2007 (just a year after the pair met), their relationship very nearly turned into marriage. In the sixth episode of the season, a drunken evening in Las Vegas turned to talk of nuptials. When Scott broached the subject at the end of the night, Kourtney was on board with the idea. This prompted Scott to get clarification, saying, "Even though we drank tonight and had a nice dinner, I need to know that your heart is in it, not just your mind 'cause you're a little drunk."

The next morning, the couple told Kardashian's family of their plans to elope and were talked out of it by Kardashian's mother, Kris Jenner. According to People, Jenner pointed out how many important family members would be missing from the moment and how a rushed Vegas ceremony was not the kind of wedding her daughter would want. Ultimately, Kardashian agreed, and the wedding was off. 

By the time the second season of "Keeping Up with the Kardashians" premiered, things weren't so rosy for Kourtney Kardashian and Scott Disick. While going through Disick's phone during the season premiere, Kardashian spotted a series of text messages that led her to believe Scott cheated on her, including texts from someone saved in Disick's BlackBerry as "My Wife." When confronted, Disick swore he never cheated. Ultimately, Kardashian believed him, at least enough to keep the relationship going. 

During a confessional interview later in the episode, Kardashian explained, "Really deep down inside, I don't feel like I'm done with the relationship so I decide to give it a chance, but really slowly and definitely not jump in with both feet."

Once the third season of "Keeping Up with the Kardashians" rolled around, Kardashian once again feared Disick was cheating on her and the pair split, leaving Kardashian single for the first season of spinoff series "Khloé and Kourtney Take Miami" in 2009.

The split didn't last long, however. As chronicled in the fifth episode of "Kourtney and Khloé Take Miami," after six months of being split, Kourtney Kardashian got a surprise phone call from Scott Disick, but didn't answer. Later, at a party hosted by record producer Scott Storch, Disick made a surprise appearance. In a confessional interview, Kardashian revealed, "I turn around and Scott is standing right behind me. Scott Storch totally set this up; I cannot believe Scott [Disick] is right here. I'm just trying to keep my composure."

Ultimately Kardashian agreed to go to dinner with Disick a few days later, then to a concert later that evening, where the pair were shown making out multiple times. The pair was then seen going back to what is later revealed to be Disick's hotel room. The next morning, Kardashian told her sister Khloé, "I thought I could control myself and I obviously can't."

While Kourtney Kardashian may have thought the biggest decision she'd have to make after her hookup with Scott Disick was whether or not to get back together with him more permanently, she didn't count on getting pregnant. She later told Us Weekly that she'd forgotten to take her birth control around the time she hooked up with Disick. "This probably sounds so dumb, but there's so many times I'll forget to take my pill and I don't think it's that big of a deal," she said. "It's just so stupid."

Sure enough, on the seventh episode of "Kourtney and Khloé Take Miami," several pregnancy tests revealed Kardashian was pregnant. After a lot of back and forth and a trip to the doctor on the eighth episode of the series, Kardashian and Disick made the decision to keep the baby and continue with the pregnancy after hearing the baby's heartbeat.

Shortly after "Kourtney and Khloé Take Miami" aired, Kourtney Kardashian announced she and Scott Disick were expecting a baby boy, due in December. She told E! News at the time, "A boy is definitely needed in this family! Scott and I are thrilled to add a little boy to the bunch." On December 14, 2009, Kardashian and Disick welcomed their son Mason Dash Disick. According to E! News, Kardashian's publicist revealed that Mason weighed 7 pounds, 6 ounces, and was 19.5 inches long. 

As People notes in their special look-back, viewers got the chance to witness the birth (and Kourtney pulling Mason out herself!) on the Season 4 finale of "Keeping Up with the Kardashians."

Prior to Mason's birth, Kardashian told Us Weekly about the type of parent she wanted to be. "I feel like you don't want to be too much their friend, and you don't want to be too strict," she said. "My dad [the late Robert Kardashian] was always the perfect balance."

Kourtney Kardashian and Scott Disick's joy at becoming parents was somewhat short-lived as Disick's partying and anger issues soon became out of control. In the eighth episode of the second season of "Kourtney and Khloé Take Miami," Kardashian and her sister Kim return home to find empty alcohol bottles and the smell of marijuana. When Kardashian confronts Disick behind closed doors, viewers can hear a scuffle and yelling, at which point Kardashian and her sister, with Mason in tow, leave. On their way out, they hear a loud crash, which is later shown to be Disick punching a mirror and badly cutting himself, ultimately requiring surgery.

In the car with Kim, Kardashian reveals Disick grabbed her arm, at which point she slapped him. While her sister pushed her to leave Disick entirely, Kardashian ends up taking some space from him. Ultimately, the pair reconciled (again) as Disick vowed to change. 

By the time Kourtney Kardashian and her sister Kim took the Kardashian spinoffs to a new city in "Kourtney and Kim Take New York," it seemed like Disick was mostly getting his act together, despite a few televised arguments with Kardashian. By the 10th episode of the spinoff, Disick felt so good about the pair's relationship that he starts considering engagement while shopping for diamonds. He tells Kardashian's sister Kim, who has joined him on the shopping trip, "I'm sitting here, I'm 27 years old, I have a son that's almost a year old and I'm going to buy earrings or a necklace one more time? I feel like at this point in my life, why am I not just buying an engagement ring?"

Later in the episode, at dinner with Kardashian, Disick broaches the subject, but Kardashian isn't sold on the idea. "If things are so good now, and we've finally come to this place, why would we want to change that?" she says.

While marriage wasn't on the table, Scott Disick and Kourtney Kardashian's relationship was on good enough footing for the pair to have a second baby. Unlike Kardashian's first pregnancy, which was entirely unplanned, her second pregnancy was a little less surprising. Disick told Us Weekly when the pair announced Kardashian's pregnancy in November 2011, "It wasn't like we weren't trying. We kind of just said, 'If it's meant to be, it'll be.'"

On July 8, 2012, Penelope Scotland Disick was born, according to Us Weekly. Like with son Mason's birth, Kardashian is the one who pulled baby girl Penelope out in the final moments of labor, with People reporting that sister Khloé Kardashian (who was in the room, along with pretty much the entire Kardashian-Jenner family) quipped, "Kourtney just loves to pull out her own children." Also like Mason's birth, Penelope's birth was televised, on Episode 18 of Season 7 of "Keeping Up with the Kardashians."

After Penelope's birth, Kourtney Kardashian and Scott Disick ran into trouble again after Disick's parents passed away, and he returned to his hard partying habits during the filming of "Kourtney and Khloé Take the Hamptons" during summer 2014. While viewers wouldn't see the footage of Disick's latest substance issues and his stint in rehab until the show aired in November 2014, it was all going down around the time Us Weekly reported Kardashian's pregnancy with the couple's third child. 

When fans finally got to see the footage of Kardashian telling Disick she was pregnant during the ninth season of "Keeping Up with the Kardashians," it was immediately clear the pregnancy hadn't been planned, with Disick proclaiming, "You just keep suckering me into these kids," and saying he couldn't handle the responsibility of another one. 

The couple's third child, Reign Aston Disick, was born on December 14, 2014, sharing a birthday with older brother Mason. Reign's birth was not televised, unlike the births of his older siblings. Shortly after his birth, as noted by Us Weekly, Kardashian kicked Disick out of the house because of excessive drinking, and in response he disappeared on a bender for several days. 

Kourtney Kardashian seemingly finally had enough of Scott Disick's ongoing bad behavior in July 2015. Over the July 4th holiday, while Kardashian was home caring for their three kids, Disick was partying in Monaco and getting especially close with his ex girlfriend Chloe Bartoli, according to Us Weekly. Enough was enough for Kardashian, and E! News reported that the pair split up shortly after the photos were published. A source told E!, "Kourtney has always taken Scott back and been by his side, but now with three kids it has gotten old. Kourtney has to do what's best for the kids."

Fans then got to see it all play out on the Season 10 finale of "Keeping Up with the Kardashians." According to Harper's Bazaar, the episode ended with Kourtney saying, "I love Scott, but I've been dealing with this for so long, it's definitely not good for me. At this point I'm really just trying to focus on me and the kids and make them the priority."

Despite calling it quits in July 2015, Kourtney Kardashian and Scott Disick continued to spend a lot of time together while co-parenting their three children. In December 2016, the pair apparently decided to move beyond co-parenting and tried giving it another shot as a couple. According to E! News, two sources confirmed that Kardashian and Disick were back together, thanks to Scott getting a handle on his partying. 

According to one of the sources, the couple's three children were the driving force behind them trying to make it work again. If the sources were correct, it definitely didn't last long. In January 2017, the Daily Mail published exclusive photos of Disick once again getting very close with someone other than Kardashian, right after returning from a vacation with the Kardashian family. Any hope of a reconciliation for Kardashian and Disick was out the window by this point.

Despite the ups and downs of Kourtney Kardashian and Scott Disick's relationship over the years, the pair seemingly finally got a handle on co-parenting in a healthy way in 2017, and, as E! News noted, have been going on vacation and celebrating holidays as a family ever since, even when they were dating other people. In a video posted to Kardashian's Poosh website in 2019, Kardashian and Disick talked about their co-parenting relationship. 

Disick revealed that the hardest part for him was separating their friendship while being on the same page about their kids, but boundaries helped. "I mean in the beginning, I think you set good [boundaries] and then we learned from that and we've gotten to a good place," he said. In the same video, Kardashian revealed that they were able to come up with their co-parenting plan on their own. "I think it's nice that we didn't have to involve attorneys, we just did it on our own," she said. "We came up with our own schedule of what made the most sense with the kids."

While Kourtney Kardashian and Scott Disick are still committed to co-parenting their three children, their relationship is no longer quite as amicable as it was between 2017-2020. Us Weekly reported in September 2021 that the pair's friendship was strained due to Kardashian's relationship with Blink-182 drummer Travis Barker after Kardashian's other ex, Younes Bendjima, posted screenshots of messages he allegedly received from Disick. The inside source told Us Weekly, "[Disick]'s trying to be the best parent he can be for their kids and make it work coparenting, but he's having problems now with Kourtney," adding, "He's worried that she's going to try to put a wedge between him and the kids."

Later that month, their relationship had apparently only worsened, with a source telling Us Weekly, "Outside of coparenting, Scott and Kourtney's relationship is nonexistent." So much for maintaining both a friendship and parenting boundaries.

According to The Blast, Disick remarked to Khloé Kardashian in the first episode of the new series, "The Kardashians," that he was struggling with having lost Kourtney as both his girlfriend and best friend. Only time will tell if Kardashian and Disick are able to repair their friendship in the future.