Though Scott Disick and Sofia Richie have yet to confirm their reported breakup, Disick is already rumored to be rekindling his romance with Kourtney Kardashian. IMO, the evidence is pretty compelling, considering the co-parents reportedly took back-to-back vacations to Utah and Wyoming together (and Kardashian posted a pic of herself possibly wearing her ex’s flannel shirt). Of course, nothing is simple when it comes to Disick and Kardashian, and during his three-year relationship with Richie, Disick’s relationship with his ex was more complicated than ever. Scott Disick, Sofia Richie, and Kourtney Kardashian’s love triangle never failed to make me cringe, and now seems like a good time to review the most awkward moments for this unexpected trio.
In Sept. 2017, just about two years after splitting from Kardashian, Disick posted some PDA-packed pics on his Insta Story, making it clear he and Richie were officially an item. The pair went on to date for three years before they reportedly ended their relationship in May 2020. According to a source who spoke to People on June 24, Richie is "still processing" her reported split from Disick and apparently isn’t too pleased Disick and Kardashian might have reconciled. IMO, three’s a crowd, and these uncomfy love triangle moments prove it.
When Disick Wanted To Have Another Baby With Kardashian In May 2018
During a Sept. 2018 episode of Keeping Up With the Kardashians (which was filmed in May 2018), Kim Kardashian revealed to her friend Larsa Pippen that Disick wanted to have a fourth baby with his ex-partner of nine years. "So Scott just texts me that he wants to have another baby with Kourtney," Kim told Larsa. "I think he just wants one more, and she wants one more." In Kim’s opinion, the fact that Disick was dating Richie and her sister was (at the time) dating Younes Bendjima wasn’t an issue. "[Scott and Kourtney] don’t even have to have sex," Kim added. "It could be IVF."
When Disick & Kardashian Went To Bali In Oct. 2018
In Oct. 2018, Disick joined Kardashian in Bali with her sisters and their kids, though Richie was notably missing from the trip. Later, in an April 2019 episode of KUWTK, it was revealed that Disick and Kardashian met with a local Bali healer, who told the exes they might be "soulmates." During the episode, the two spoke at length about what this meant for their relationship, as well as Disick’s relationship with Richie.
"We’ve come to such a good place," Kardashian explained to her sisters, referring to Disick. "We’re finally able to travel together as a family. There’s so many positives. But the whole soulmate thing comes up — I don’t know. It’s just a lot to think about." Later, after chatting with Disick, Kardashian said, "I don’t know what the definition of ‘soulmate’ is, but Scott and I, we’re going to be in each other’s lives forever. We are soulmates in a sense. No matter what, whether we’re ever together again or not."
When Kardashian Third-Wheeled Richie & Disick Twice In Nov. 2018
Soon after returning from their Indonesian vacation, Kardashian and Disick were spotted grabbing sushi with Richie at Nobu in Malibu, California. "It was a quick dinner," a source reportedly told People. "It seemed a bit tense. It wasn’t like they are all friends and were hanging out for fun. It looked more like a business dinner." A few weeks after that, the trio attended the VIP preview for the Street Dreams gallery exhibit.
When Kardashian & Disick Posed In Bed In Dec. 2018
In Dec. 2018, Kardashian raised eyebrows after she posted a saucy pic of herself on Insta lounging on a bed while Disick and their daughter, Penelope, bonded in the background. "Coparenting," she captioned the pic.
Just a few weeks before that, Kardashian revealed in another IG post that she and Disick had a sleepover together the night before Thanksgiving. "I woke up this morning in bed with my children, in the same house as my sisters (minus @khloekardashian 😩😢i miss you), my brothers, the father of my kids, my mommy, my grandma, my nieces and nephew. I feel beyond grateful. Happy Thanksgiving!" she captioned the pic, which showed her and Disick together with their three kids.
When They All Vacationed In Cabo In Dec. 2018
Later on in Dec. 2018, Richie joined Disick, Kardashian, and their brood in Cabo over the holidays. "Kourtney, Scott, and Sofia are one modern family. Things are totally fine," an insider reportedly told Us Weekly. "It wasn’t a surprise that Sofia went away with them — it was a family trip. Sofia and Scott are together, they are in love, and she’s part of the family now." Disick took to IG to post a pic of the trio, which he captioned, "What more can a guy ask for. THREE’S COMPANY."
When Richie Joined Disick & Kardashian In Aspen In Dec. 2018
Right after Cabo, Disick and Richie joined a few members of the Kardashian clan (including Disick’s ex) on a ski trip to Aspen, Colorado, to ring in the New Year. At one point, the trio enjoyed an intimate dinner together at Italian restaurant Casa Tua.
When Kardashian Invited Disick & Richie To Finland In April 2019
Kardashian celebrated her 40th birthday in April 2019 with a family trip to Finland, and Disick and Richie were invited to tag along. "The family trip was for the kids’ spring break. This is why Scott and Sofia came along," a source reportedly told People. "They spent several days in Finland and had a great time."
Later, during an Oct. 2019 episode of KUWTK, fans learned just how awkward the family vacation had been. In addition to an uncomfy hot tub moment (where Kardashian critiqued Richie’s makeup and Disick and Kardashian bickered), Richie noted how Disick’s behavior changed when he was around his ex. "You’re a lot more sophisticated with me when Kourtney is around," she said. Disick also confessed to Kardashian during the episode that keeping both her and Richie happy was stressful for him.
When Disick Spent His Birthday With Both Richie & Kardashian In May 2019
Disick celebrated his 36th birthday with small gathering at home, which both Richie and Kardashian attended. At one point, the three even posed for a photo booth pic together (along with Kylie Jenner). Though Kardashian didn’t post a tribute for Disick on IG, Khloé Kardashian shared a series of photos and called Disick her "brother" and "one of [her] best friends," while Kim also referred to Disick as someone who felt "like [her] brother" in her own birthday tribute.
Co-parenting is tough enough without a third party involved, but here’s hoping Disick and Kardashian are able to do whatever’s best for themselves and for their kids.
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