and have known each other for almost two decades and while they now have an amicable relationship, . The pair in 2006, but it wasn't love at first sight. Kourtney admitted she found Scott "annoying" and was worried about their four-year age-gap. Despite initial worries, Kourtney and Scott soon started dating and . However, the couple had a turbulent romance which was marred by cheating allegations and addiction struggles. Here, we've taken a deep dive into Kourtney and Scott's relationship timeline. Kourtney and Scott first started dating in 2006 after meeting at Joe Francis' home in
Mexico. The couple later opened up about their first encounter and admitted they almost never got together. "I liked her but she wanted nothing to do with me," Scott said on an episode of Kourtney and Khloe Take the Hamptons. Kourtney added: "I just thought he was so annoying. He was four years younger, he lived in
New York, he didn't have a
Job." Scott was first introduced to the public as Kourtney's boyfriend on the season premiere of
Keeping Up With the Kardashians. "We were
Friends for about a year and then started dating, and have been together ever since," Kourtney explained. Kourtney's family initially had concerns about Scott. During the episode, momager Kris Jenner said: "To me, he's really young and I just don't see somebody his age settling down into that kind of life right now." However, Scott insisted he was committed to Kourtney and said he loved her "to death". He added: "I will never do anything to disrespect your daughter." After a year of dating, Kourtney and Scott almost tied the knot in
Las Vegas after a night of partying. "Would you hate it if I asked you to marry me right now, or tomorrow?" Scott asked as they headed to their hotel room. Kourtney agreed and the two even made it to the Little White Chapel, but Kris Jenner stepped in before Kourtney could make it down the aisle. "This feels wrong. You're rushing it," Kris told her daughter. Kourtney and Scott agreed not to get married. "I guess Scott and I will just keep living in sin," Kourtney said. In May 2008, Kourtney and Scott split for the first time after the Poosh founder and her sister
Khloe Kardashian discovered texts on Scott's phone from someone called "my wife". Kourtney became convinced Scott was cheating on her and confronted him on the season two premiere of Keeping Up With the Kardashians. "I cannot believe Scott could have cheated on me. I'm sick to my stomach that this could have happened," she said to the cameras. Their split didn't last for long and in August 2009, Kourtney announced she was pregnant with their first child. "We were in the Everglades, and I kept feeling nauseous and sick. I just kept thinking something wasn't feeling right," Kourtney said at the time. She added: "I've never missed a period in my life. Literally, I took like 20 tests; I went to the doctor and he confirmed the news. I was just so shocked." Kourtney gave birth to son Mason on December 14, 2009. The Poosh founder infamously pulled out Mason herself during the birth, which was later featured on an episode of Keeping Up With the Kardashians. Kourtney and Scott split for the second time when he punched a minor following a night of drinking. "I don't know where this crazy anger comes from. He gets this crazy rage inside of him that's not okay," Kourtney said during an episode of Kourtney and Kim Take Miami. She told Scott their relationship was over until he got help for his behavior. Days after the episode aired, Kris Jenner revealed the couple were working on their relationship. It was then revealed they had decided to go to couples therapy. Kourtney and Scott also went on to welcome daughter Penelope Disick, having announced they were expecting their second child on November 30, 2011. Kourtney's sister
Kim Kardashian said at the time: "It's so exciting. They are so happy and so am I!" Kourtney gave birth to Penelope on July 8, 2012. "Scott and I are overjoyed to welcome our precious angel Penelope
Scotland Disick into our lives. We are forever blessed. Mommy and baby are resting comfortably," Kourtney said in a statement. In June 2014, it was revealed Kourtney was expecting her third baby. A source told : "She's really excited but she's nervous too. "Three kids is a lot to handle! But she's happy — she's always wanted a big family with Scott." On December 14, 2014, Kourtney and Scott welcomed son Reign Disick. Kourtney shared a snap of their new addition on
Instagram. She wrote: "Madly in love with my little Reign Aston Disick." Cracks started to show in their relationship in March 2015 when Scott checked in to Rythmia Life Advancement Center (RLAC) in Costa Rica. "I realize my issues are bigger than me and I'm ready to truly remedy this struggle I continue to battle," he said in a statement. Kourtney initially stood by her boyfriend, but she ended their romance four months later after pictures emerged of him cozying up to his ex-girlfriend Chloe Bartoli. The split was featured on an episode of Keeping Up With The Kardashians. "I'm literally on the verge of a mental breakdown," Kourtney said. "I can't believe that this is where my life is at right now. I've worked so hard to keep this family together, it just makes me sad for the kids." Kourtney added: "He's not being a good partner to me. I could never rely on him, depend on him for one single thing and I don't want to show my kids that that's okay. "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." All the latest news, showbiz, lifestyle and sports updates, brought to you by our dedicated
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