TBT: Kourtney Kardashian Thought Scott Disick Was "So Annoying" When They First Met

"He was four years younger; he lived in New York; he didn't have a job."

Who: Reality star and founder of the lifestyle website Poosh, Kourtney Kardashian, 43, and reality star, house flipper, and fashion founder Scott Disick, 39.

How They Met: Kourtney and Scott met a year before the cameras started rolling for Keeping Up With the Kardashians. In 2006, the two were introduced during a party at Girls Gone Wild creator Joe Francis’s home in Mexico, but Kourtney wasn’t into Scott at first.

"I liked her. But she wanted nothing to do with me," Disick said of their initial encounter during an episode of Kourtney & Khloé Take the Hamptons in 2014. Kourtney confirmed Scott’s impression to be accurate, adding: “I just thought he was so annoying. He was four years younger. He lived in New York. He didn't have a job."

Eventually, Scott's charm won her over, and by 2007 the world began to witness their love story unfold (and the many ups and downs that went along with it) on KUWTK. Aside from her family’s apprehension about their relationship, Kourtney and Scott’s love was pure. The pair even almost got married after a night out in Vegas during the show's first season.

However, the honeymoon period didn’t last long, as they broke up for the first time in 2008 after Kourtney found inappropriate texts in Scott’s phone to a person called “my wife.”

But within a year, Kourtney revealed that she was pregnant with her and Scott’s first child, and in December 2009, the couple welcomed Mason Dash Disick. Following another brief breakup in 2010, Kourtney and Scott expanded their family again, welcoming a daughter, Penelope Scotland Disick, in 2012 and another son, Reign Aston Disick, two years later.

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Why We Loved Them: In light of Scott's behavior and Kourtney's apathetic attitude, these two were really, truly in love. We saw glimpses of it every now and then (Scott asking Kourtney to marry him on a whim more than once, or the time he sweetly recreated a scene from The Notebook after she said she needed more romance). Plus, she was patient enough to put up with his Lord Disick antics while he accepted her organic, gluten-free, dairy-free lifestyle — albeit not without a bit of humor.

Fans of the show were convinced they were soulmates, and a healer even told them they were destined to be together during their family vacation to Bali in 2019. "Scott came in, and the guy was basically saying that in a past life, we were together and that we’re soulmates,” Kourtney told her sisters about their reading. “He was like, ‘You have to decide if you want to be together or not be together.’ ”

When They Peaked: With so many moments to choose from over the course of their nine-year relationship playing out on TV, it’s hard to pick just one. But if we absolutely have to, it would be the time Scott volunteered to shave Kourtney’s lady parts while she was pregnant and couldn't see over her belly.

Now, that’s next-level love and commitment.

The Breakup: In 2015, Kourtney and Scott officially called it quits on their relationship amidst cheating allegations. While vacationing without Kourtney, photos of Scott getting cozy with stylist Chloe Bartoli in France began circulating on the internet, prompting their final split.

Kourtney later spoke about the breakup during the season 10 finale of KUWTK. "I'm literally on the verge of a mental breakdown," she told her family. "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."

She continued, “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."

Shortly after they split, Scott entered rehab for drug and alcohol abuse following Kourtney issuing an ultimatum about him being able to see their three children (she was reportedly seeking sole custody).

Despite not ending their relationship on the best of terms, today, Kourtney and Scott are good friends and even better co-parents. During the KUWTK reunion, Kourtney told host Andy Cohen that she and Scott are “great friends and co-parents,” to which Scott added: "I mean, we're family. I think we always will be."

Scott even offered his support of Kourtney and her now-husband Travis Barker’s relationship on the show. "I think if you really love somebody, you want them to be happy no matter what,” he said. “So I do give her a blessing to be happy." And Kourt agreed: "Whoever would make him happy, I would give my blessing."

Where They Are Now:  A few months after the breakup, Kourtney reportedly began seeing Justin Bieber before entering her first serious relationship post-Scott in 2017. Kourtney made her couple debut with French model Younes Bendjima in Cannes, but after a little over a year of dating, they split. In 2021, it was confirmed that she was dating Travis Barker, and following a year-long courtship, the pair got married in Italy last summer.

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Seemingly not quitting reality TV anytime soon, Kourtney continues to make appearances on her family's new Hulu show, The Kardashians. On Thursday (April 13), the streaming platform will be airing a wedding special documenting her and Travis's nuptials.

Scott moved on from his relationship with Kourtney with Sofia Richie in 2017, and the pair dated for three years. In May 2020, they called it quits for the first time before getting back together and breaking up a few more times in the following months. Scott then began seeing model Amelia Hamlin, but less than a year later, they ended things. His latest rumored romance has been with Rod Stewart's daughter, Kimberly Stewart.

As for work, Scott is still a supporting character on Hulu's The Kardashians and also manages his fashion brand of luxury leisurewear, Talentless, while flipping houses on the side.

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