People May Be Calling For Khloé Kardashian And Scott Disick To Date Now, But They Actually Have An Incredibly Complicated History

If you’d forgotten that Khloé and Scott once got into such a brutal fight that Khloé had to seek anger management classes, you’re gonna need to read this.

Celebrations were in order during this week’s episode of The Kardashians as the family came together for Scott Disick’s 40th birthday dinner.

Close-up of Scott sitting at a table with a crown next to him

In May, the KarJenners — minus Kourtney — marked Scott’s milestone with a regal dinner party, where they took the time to reflect on their history with Lord Disick.

Close-up of Scott and the KarJenners around the table

“Scott, I feel like I have known you most of your adult life,” Kris Jenner began, raising a toast to the birthday boy. “You were literally here Episode 1, Season 1.”

Close-up of Kris holding a glass and wearing a crown

Kim followed suit by calling Scott her “brother” and praising him for sticking by her throughout “every phase” of her rise to fame. “I have known Scott for 19 years,” she said. “Scott has supported me through thick and thin, ’cause that’s who you are.”

Close-up of Kim raising a glass and smiling

However, neither of their tributes was a match for Khloé’s, which hinted at her and Scott’s seriously messy beginnings back in the 2000s.

Close-up of Scott in a suit and tie and Khloé in a flared miniskirt

“When we first met, you and I definitely had tension, but I really think it’s the most genuine, real relationship,” she said. “It didn’t start fake, it didn’t start forced.”

Close-up of Khloé in a crown and animal-print outfit

She said, “I was really just, like, determined to not like you, and, like, you came into my townhouse and took up my space, and I was like, ‘This guy, get out of our little place,’ and now I love you genuinely.”

Close-up of Khloé in a crown and animal-print outfit

Like Kim, Khloé concluded by saying she considers Scott to be her “brother,” adding, “I love you, I adore you, I want the best for you. You will find the best and the best will find you, because that’s all you deserve, is greatness, and I love you.”

Close-up of Scott sitting with his hands clasped under his chin

Now, if you know anything about the Kardashians, you’ll know that Khloé and Scott’s relationship development over the past 16 years could probably rival the plot of a Hollywood movie.

Close-up of Scott with Khloé, Kim, Kourtney, and Kris at a media event

And while the Good American founder stands as Scott’s closest ally in the family today, the current state of their relationship quite literally couldn’t be more different from where they started in 2007 — the year that Keeping Up With the Kardashians premiered on E!.

Screenshot of Scott

As Kris recalled in her speech on The Kardashians this week, a then-24-year-old Scott was introduced as Kourtney’s boyfriend in the very first episode of KUWTK. And in his first-ever scene, it was immediately evident that Kourtney’s family — namely Kris and Khloé — were not on board with the relationship, with Khloé warning her sister that Scott might be a “fucking psycho” because he’s a Gemini.

Screenshot of Kourtney and Scott standing together

By the Season 2 premiere, it looked as if Scott and Kourtney might be done for good after they split over allegations that Scott had cheated. Khloé and Kourtney were BFFs at this time, so she wholeheartedly supported her sister’s decision to cut Scott out of her life permanently, and even took it upon herself to call him out on his infidelity face-to-face.

Screenshot of Khloé

“Whatever goes on between you and Kourtney is really between you and Kourtney, but when you hurt Kourtney, you hurt me,” she said after privately cornering him in a restaurant. “You can fuck her over once, and if she accepts it, cool. But if you do it twice, I will cut your fucking balls off.”

Screenshot of Khloé and Scott at a restaurant

So this pretty much set the tone for Khloé’s “no bullshit” attitude toward Scott. And from this point onward, it was more evident than ever that the pair were firm enemies.

Screenshot of Scott

As you might recall, things only got messier between Scott and Khloé when it was revealed that he and Kourtney had been hooking up during their relationship break — resulting in an unplanned pregnancy.

Screenshot of Kourtney and Khloé in a bathroom

In a tense episode of Kim & Kourtney Take Miami, Kourt nervously informed Khloé that she was pregnant, which led her sister to brutally lash out at Scott, accusing him of trying to trap Kourtney with a child.

Close-up of Scott and Kourtney sitting together

“He’s doing this intentionally to keep you…to keep you around because he’s fucked up how many times?” Khloé yelled at Kourtney and Scott before describing him as a “snake” who “knows he could never get someone as good” as Kourtney.

Close-up of Khloé looking upset

Once it became clear that Kourtney and Scott were serious about growing a family, Khloé eventually decided that she and Scott needed to put their “issues aside” for the benefit of baby Mason — although they didn't stay on good terms for long.

Screenshot of Khloé

In a Season 4 episode of KUWTK that aired in late 2009, Khloé declined to attend a gender-reveal hospital appointment that Scott planned, telling Caitlyn Jenner and Kris at the time that she wouldn’t “support anything” he was involved with.

Screenshot of Scott sitting

And while the rest of the family were coming to terms with the fact that Scott would be in their lives forever, Khloé was the only KarJenner still staunchly reluctant to accept him — saying in her confessional that he’s “still a douche” and she’s “allowed to despise him” for “screwing up [her] sister’s life.”

Screenshot of a pregnant Kourtney in bed and surrounded by her family

“My problem with Scott is that he’s a con artist,” she said. “He’s annoying, and honestly, someone needs to beat the shit out of him.”

Screenshot of Kourtney sitting

At this point in the timeline, tensions between Scott and Khloé were so bad that Kourtney was seriously considering a move to New York just to get away from it all. And things ultimately got worse when — after a few too many drinks at an awkward dinner — Khloé doubled down on her theory that Scott impregnated Kourtney so she wouldn’t leave him.

Screenshot of Scott wearing a cap

“You thought she was gonna slip away from you; that’s why you knocked her up,” Khloé said. “You wanted to keep her for 18 years and not let anybody else have her.”

Screenshot of Khloé with her arm around a seated Scott's neck

The argument escalated to a physical altercation between the pair, with Khloé smacking Scott across the face, prompting Kourtney to walk out. After things got physical, Khloé realized the situation had gone too far, and she wound up attending anger management classes to deal with her feelings toward Scott.

Screenshot of Khloé attacking Scott

In the classes, a professional helped Khloé carefully unpack her grievances relating to Scott, leading her to come to the conclusion that her “anger” was less about him and more about the fact she felt she was “losing Kourtney.”

Screenshot of Khloé

After all that, Khloé and Scott managed to smooth things over once again, with Khloé taking responsibility for the slap. However, things continued to be rocky after Scott’s excessive drinking became an issue for the entire family, with Kourtney telling Scott that they couldn’t be together until he was able to work on himself.

Screenshot of Scott

Fast-forward to Season 5, and while Kourtney and Scott were still patching up their relationship after Mason’s birth, Khloé hated Scott so much that she refused to let him into her home.

Screenshot of Scott in a suit and tie

Around the same time, Kris resorted to begging Khloé to start embracing Scott as the family stressed that the tension between the two of them might cause Kourtney and Scott to follow through with their permanent move to New York.

Screenshot of Kris

“Kourtney is your best friend and Mason is your nephew. So if you don’t try to stop this, you’re gonna lose both of them,” Kris begged. “Don’t you care?”

Screenshot of Khloé seated and looking upset

Eventually, Khloé reluctantly came around to the idea of embracing Scott with a belated birthday party, but she ultimately made things worse when Kourtney said it was “obvious” that she didn’t really care about being nice to him.

Screenshot of Kourtney

For years after this, Scott’s drinking habits and excessive partying forged a major wedge between him and Kourtney’s entire family, and — as usual — Khloé made a point of speaking her mind and defending her sister.

Close-up of Khloé and Scott standing together by a doorway

But being the nurturing person she is, Khloé also started becoming more supportive of Scott as he sought to better himself over the years — serving as somewhat of a mediator throughout Kourtney and Scott’s continual relationship issues, leading up to the eventual demise of their relationship in 2015.

Close-up of Kourtney and Scott

Since then, Khloé, along with Kris, has continued to extend the olive branch to Scott, despite Kourtney’s desire to distance him from the family. And he has returned the favor by supporting Khloé through her own relationship troubles, namely with Tristan Thompson.

Close-up of Khloé and Scott sitting together

As you’ll probably know, an aspect of Khloé and Scott’s sibling-like bond — from their brutal arguments to their sense of humor and shared love of pranks — has been fan speculation that the two are actually destined to be together romantically.

Close-up of Khloé and Scott walking together

And it’s a narrative that the pair have playfully leaned into over the years — particularly Scott, whose Instagram page is filled with countless jokes about him and Khloé being “relationship goals.”

Close-up of Khloé and Scott

In fact, after years of rampant speculation that Scott and Khloé might really be endgame, Scott said earlier this year that Khloé is actually his dream girl.

Screenshot of Scott

“She’s funny, she’s kind, she’s sweet, she’s cute…she’s got all the characteristics I want,” he said during a recent episode of The Kardashians, in which Khloé and Kris attempted to set him up on a blind date. “Obviously I'd never look at Khloé sexually, even though I make jokes like that,” he added.

Screenshot of Kris, Khloé, and Scott in a living room

Well, if these two were able to go from sworn enemies to the ultimate BFFs, perhaps anything is possible.

You can stream all four seasons of The Kardashians on Hulu in the US and on Disney+ internationally.

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