Sofia Richie and Scott Disick’s Complete Relationship Timeline, Including Kourtney Kardashian’s Feelings on It

When the world initially got wind that Scott Disick and Sofia Richie were embarking on a relationship, despite their 16-year age gap and all, the reviews were decidedly mixed. Age aside, many still held hope for the on-and-off roller coaster that was Disick’s romance with Kourtney Kardashian. But, like it or not, Richie and Disick went strong for about three years. It was recently reported that the couple has split for the second time in three months, as Disick vacations in Idaho with Kardashian and their kids. Here, a reflection on how the self-proclaimed Lord (at one time) found his rightful Lady.

May 2017

Back in late May 2017, several outlets reported that Scott Disick and Sofia Richie were spotted getting to know one another on a yacht in Cannes. Richie even posted a photo of herself on said yacht, although the pair stayed mum on romance rumors. The following month, Disick and Richie were also seen leaving Nobu together, stoking speculation further.

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September 2017

After months of people wondering about the state of their relationship, Disick and Richie were sporadically spotted together until September 24. Then, they appeared on each other’s Instagram Stories. The new couple even got a “Congratulations” cake at a restaurant, perhaps a nod to their making their relationship official.

An insider told E! News at the time, “Sofia has been interested in him for a long time. She feels like she knows a different side of him and that they are good for each other. She is falling hard and thinks this is the real thing.”

Meanwhile, an Us Weekly source close to Disick’s ex Kourtney Kardashian said Kardashian wasn’t getting too invested in the two dating. “Kourtney thinks this fling with Sofia is a little weird, but nothing shocks her anymore,” the source claimed. “Kourtney just wants Scott to be his old self. She shares three kids with him, so she’ll always want the best for him and will always make sure he’s happy.”

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October 2017

The new couple went Instagram (grid) official, Richie posting a picture of the two in Puerta Vallarta, Mexico. However, just days later, her dad Lionel Richie told Us Weekly that he was “scared to death” of his then 19-year-old daughter’s relationship with a 34-year-old.

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Even skeptical commentary from dad didn’t stop Richie from sharing her newfound happiness, posting a photo of herself and Disick boating in Venice. She captioned it, “Run away with it.”

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December 2017

Disick and Richie made their official debut as a couple at a DuJour magazine event in Miami. Although they didn’t walk the red carpet together, pictures of Disick with his arms wrapped around Richie came out.

DuJour's Jason Binn And WellNEST Celebrate Miami Beach's Art Basel Kick-Off

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The burgeoning couple also made time for a Sugar Factory appearance in Miami, which would become a staple for their public dates.

Scott Disick Art Week Party With Sofia Richie At Sugar Factory American Brasserie On Ocean Drive In Miami

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By the end of 2017, both Disick and Richie seemed “all in” on their coupling, each publishing New Year’s posts that emphasized their being a united front. “I’m on a whole new year vibe,” Disick captioned his snap of them in Aspen.

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January 2018

2018 begins much as it ended for Disick and Richie, each posting pictures of them traveling.

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But the couple’s bliss doesn’t last for too long when Kendall Jenner commented on a Scott Disick Instagram fan account photo of him with his kids and Richie in the car, “Aww Scott and his kids,” she wrote. Jenner’s trolling of Richie continues into February.

February 2018

A slew of developments for Disick and Richie occur this month. On Valentine’s Day, Richie posted a cuddly black-and-white picture of the pair.

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Disick potentially gives an even more valuable Valentine’s Day gift—confirmation of their love on an episode of Keeping Up with the Kardashians. Although it’s difficult not to cringe when Kris Jenner corners Disick over his age gap with Richie…

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By the end of the month, Lionel Richie spoke out again about his daughter’s relationship, calling it “a phase.” However, a source told Us Weekly that Richie had been “a great influence” on Disick.

“Scott wasn’t bothered by Lionel’s recent comments that basically said, ‘It’s just a phase’,” the source explained to the outlet. “He gets it and understands and knows how close Sofia is with her dad, and he respects that relationship…Sofia still hasn’t hung out around Scott and Kourtney together.”

March 2018

Richie posted a photo of herself and Disick posing in front of a private jet captioned, “My ❤️.”

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May 2018

Per People, Richie and Disick spend his birthday in St. Bart’s with all three of his kids: Mason, 9; Penelope, 7; and Reign, 4. Richie captioned a photo of the two in an ocean, “Happy Birthday babe! Thank you for being you.” The family trip was also the first real indication that Kourtney Kardashian had warmed up to Disick’s relationship with Richie, nearly a year after Disick and Richie first branded themselves as “homies.”

This was backed up by a People source who said, “Sofia is helping Scott be a better, healthier person. Kourtney feels confident that Scott and Sofia takes good care of the kids. Scott is a great dad when he has his life together.”

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June 2018

Shortly after the couple’s fun in the sun, Disick reportedly packed on PDA with another woman during Kanye West’s album listening party in Wyoming. According to Us Weekly, Richie had left Disick after he was unfaithful in Miami.

But as quickly as the split rumors broke, both Disick and Richie were posting Instagrams dispelling them. Disick posted a screenshot of a TMZ article to his Instagram Stories captioned, “We had no idea we even broke up but thanks for thinking of us.” For her part, Richie shared a photo of herself and Disick captioned, “Whole ❤️,” followed by another photo labeled, “Never believe the internet.” Reports even claimed that the couple was planning to move in together later in the summer.

Disick cryptically captioned a photo of the couple, “Nobu.” (Deep.)

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July 2018

Richie shared a photo of herself and Disick on a Grecian getaway.

An Us Weekly source said that Kourtney “couldn’t be bothered by the drama” that had transpired between Richie and Disick the month before. “She just cares about the kids and that they’re okay with the situation, which they are.”

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October 2018

Richie proves things between her and Lord Disick are stronger than ever, sharing a sultry picture of herself posing on a bed. A mirror reflection shows that Disick is behind the lens.

Disick and Richie also made an appearance at the VIP grand opening of Maddox Gallery in LA, where they also met…Real Housewives of Beverly Hills‘ Mauricio Umansky?

The VIP Opening Of Maddox Gallery With Inaugural Exhibition "Best Of British"

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November 2018

The couple shopped at the Chadstone Shopping Centre in Melbourne.

Scott Disick Windsor Smith Store Appearance

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Richie and Disick stopped by the “Street Dreams” exhibit preview in West Hollywood, where Kourtney Kardashian was also spotted separately the same night. Per People, all three even got together for dinner at (where else?) Nobu. The People source clarified that Kourtney “doesn’t necessarily care to get to know Sofia better, but she feels she needs to because of the kids.”

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December 2018

Despite sources claiming that Sofia “knows that Kourtney isn’t her biggest fan,” Disick made a major statement by posting a photo of himself lounging poolside between his ex and current girlfriend in early December. He captioned it, “What more can a guy ask for. THREE’S COMPANY.”

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Sofia even joined the KarJenner family’s New Year’s Eve trip to Aspen, signaling that more or less, everyone had made peace with Disick’s May-December relationship. Later that month, Richie posted a picture of the pair captioned, “My kind of off roading.”

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January 2019

Disick and Richie paid a visit to Sugar Factory. Also, talk of the pair having a baby together popped up. “It’s more likely that she gets pregnant before they get engaged,” a source told Us Weekly at the time.

Scott Disick And Sofia Richie Enjoy Dinner At Sugar Factory American Brasserie At Fashion Show In Las Vegas

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February 2019

Richie and Disick had another date (that may or may not have been sponsored) at their beloved Sugar Factory.

Scott Disick And Sofia Richie Celebrate Valentine's Day At San Diego's New Theatre Box® Entertainment Complex With Dinner At Sugar Factory American Brasserie

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Scott Disick And Sofia Richie Celebrate Valentine's Day At San Diego's New Theatre Box® Entertainment Complex With Dinner At Sugar Factory American Brasserie

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April 2019

Richie and Disick walked the red carpet of an ASOS event.

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May 2019

For Disick’s 36th birthday, Richie posted a pair of black-and-white photo booth shots from his party captioned, “Best night celebrating you @letthelordbewithyou 📌 an amazing soul. we all love you very much.”

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June 2019

While Disick and Kourtney took a family vacay to Costa Rica sans Richie, the world shouldn’t get too worried about a breakup. Us Weekly even reported that the couple of more than two years had “talked seriously” about getting engaged.

An Us Weekly insider said that the couple is reportedly “in a great place and stronger than ever.” Another source even claimed that Kourtney would be “not only unbothered by the idea of them getting engaged, they’d have her full support. Sofia is really so good with his kids, and she has a good friendship and relationship with Kourtney.”

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This was also the month that KUWTK fans got to see the fallout from Disick’s Instagram post of Richie and Kourtney Kardashian together. In a clip from the show, Kris Jenner, Kim Kardashian, and Khloé Kardashian also question the boundaries between the three.

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July 2019

Ahead of Disick’s new home renovation show Flip It Like Disick, he opened up to Us Weekly about what Richie’s support of his new design career has meant to him. “She’s unbelievable,” he told the outlet. “She’s not really into architecture really, per se, so it’s different in that, but she and I have a great rapport.”

Celebrity Sightings In Los Angeles - May 15, 2019

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August 2019

Richie celebrated her 21st birthday with Disick by her side. Surprise festivities commenced at Wynn Las Vegas and the guest list included her boyfriend, Kylie Jenner, and Anastasia Karanikolaou. “I’ve been thinking about my 21st birthday for years,” she told ELLE.com before her big day. “It’s a birthday I think we all look forward too. What better place to spend it than Las Vegas with all my closest friends?” Disick’s present for Richie was casually an Aston Martin.

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Disick and Richie at her 21st birthday party.

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October 2019

A new episode of Keeping Up With the Kardashians granted viewers insight into the dynamic between Disick, Kardashian, and Richie. During a family getaway to Finland, Disick traveled with both his ex and new girlfriend, alongside his three children. “I never want to miss out on anything when it includes the kids,” he said about attending the trip during a confessional, via People. “The past six to eight months, we’ve been on a couple trip where it’s been Kourtney, Sofia, the kids, and it’s been great. But Sofia mentioned to me that she feels a little left out so I have to be careful not to overstep anyone’s boundaries and make anyone feel left out.”

He added that Richie appearing on camera for the first time also impacted the traveling situation. “Traveling with a family like this is a unique situation that not everyone does. I definitely think this trip, out of the other trips we’ve been on, has a little bit more pressure because the truth of the matter is, there are camera crews everywhere,” Disick said. “Tons of people walking around that Kourtney and I have known for over ten years. Sofia has never really done anything like this before. It’s hard. I don’t want her to feel out of place, I don’t want her to feel like she’s not as comfortable as I am. I’m just trying to be cautious of everyone’s feelings.”

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Disick even admitted that his years-long history with Kardashian could make things uncomfortable for Richie. “Sometimes you have so many inside jokes or inside things with somebody you’ve known for so long, even if you’re not romantically with them, you don’t really know how to act,” he confessed. “It is definitely a really hard and awkward situation, and I just feel bad. At the end, I want the people I love in my life to be happy.”

For Halloween, Richie and Disick dressed as a vintage-inspired Barbie and Ken. “Ken&Barb👫,” Richie captioned her post, including a reference photo of the actual dolls.

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December 2019

Two years into his daughter’s relationship with Disick, a source said Lionel Richie still didn’t totally approve of their romance. “Lionel has accepted their relationship but still isn’t entirely 100 percent on board with Scott mostly because of the age difference and how young Sofia is,” the source told E!. “Lionel can see how happy Sofia is though so he is definitely making more of an effort with Scott.”

The insider added that the three had spent Thanksgiving together and that Lionel’s bond with Sofia is most important. “He is a really honest, up front kind of guy and feels like his father-daughter relationship with Sofia is more important than anything so he’s trying to be there for Sofia and to be supportive of her despite his reservations about her relationship,” E!’s source said. “They all had a really great holiday together though and progress is for sure being made between Lionel and Scott.”

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February 2020

Some sensed that their could be behind-the-scenes drama when Richie quietly unfollowed Kourtney Kardashian on Instagram. Her decision came shortly after she told Entertainment Tonight she would no longer be appearing on KUWTK and instead pursue acting full-force.

March 2020

The following month, Richie mostly steered clear of talking about her relationship with Cosmopolitan. However, she did make clear that conversation about their age gap didn’t bother her. Richie said she had “this weird thing where I just don’t care what people think.” The speculation concerning their romance “doesn’t bother me because I’m very happy,” she added. “Why would I let someone from the middle of nowhere ruin that for me?” Richie went on to say that it’s “great” she’s dating someone who is older and pointed out the fact that her parents were 18 years apart in age.

May 2020

On May 4, E! confirmed that Disick was seeking treatment related to substance abuse issues at an Edwards, Colorado facility. Shortly after news broke, he had reportedly checked out. Attorney Marty Singer issued a statement, stating Disick planned to sue the facility for allegedly leaking the photo of him.

Singer said, “In an effort to finally come to terms and deal with the pain that Scott has been silently suffering for many years due to the sudden death of his mother, followed by the death of his father 3 months later, Scott made the decision to check himself into a rehab facility last week to work on his past traumas. He did not check in for any alcohol or cocaine abuse. Shockingly as a result of the HIPAA violation of the facility and his violation of privacy, he has checked himself out and is immediately returning home. We are alarmed by this extreme invasion of privacy and plan to take immediate legal action.”

E! reported that Richie and Disick had been quarantining together, but that Disick was struggling with “harbored pain that will surface and put him in a bad place,” per a source. Another insider told the outlet that Richie became “extremely concerned with the choices he was making and how out of control he became very quickly.” Richie “tipped off” Kourtney Kardashian about Disick’s state, “because she didn’t know what else to do.” A third source claimed, “Kourtney was very upset, and knew something was up by his unresponsiveness to matters and convos that pertained to the kids. She had been through this before many times, and put a halt to it immediately. She ultimately gave him an ultimatum and he had no choice but to seek help.”

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Disick and Kardashian in 2015.

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Shortly after, TMZ photographed Richie out with a new mystery man and claimed she had been staying at his Malibu beach house. That report seemed to suggest Richie had begun dating the unidentified person, but E! reported on May 15 that the couple was still together.

But by May 21, E! reported that their may be trouble in paradise. A source said of Richie and Disick’s relationship, “She has been giving Scott space to figure out his next steps, but has consistently been supporting him. Their relationship has been three years of ups and downs, but she isn’t leaving him to the dust. She’s very loyal to Scott.”

The source added that Disick was still devoted to spending time at home. “He hasn’t wanted to leave the house since his rehab exit, so Sofia will go and hang with friends by herself to get away and let Scott have space,” the source continued. “Scott has been in a very vulnerable place this last month and sometimes it is best for their relationship if they have space and do their own thing. It’s been hard on Sofia to see Scott in a vulnerable state but she is still standing by him.”

Page Six reported on May 27 that Richie and Disick had officially called it quits. A source said the relationship “ran its course,” and that other factors, including Disick’s “past traumas,” caused strain. “Scott had gone back to his old ways, and Sofia got fed up,” the source added. The insider also claimed his close bond with Kardashian may have been a factor. “Kourtney didn’t make it easy for her, and you can only tolerate that kind of treatment for so long,” Page Six’s source claimed.

After the split news broke, a source told E! that Disick had been spending time with Kardashian and their kids in Utah. “Scott went with Kourtney and the kids to Amangiri [a five-star resort in Canyon Point, Utah] to celebrate his birthday and enjoy the holiday weekend,” a source told the outlet. “He is doing a lot better and is focused on healing. He’s talked with a few therapists who are helping him talk through his struggles and navigate his next moves.”

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The insider continued, “Kourtney knows how to handle Scott and he is always in a better headspace when he gets to spend time with his kids. She has really been there for him since his rehab exit, and has had a lot of sympathy towards him.” She hopes to see Disick “healthy,” the source said, because it’s “best for their family and makes the dynamic much easier.” The source also said Disick was remaining in contact with Richie. “Scott and Sofia are still in touch,” the source continued. “They are definitely still spending time apart for now. Sofia wants to make sure Scott gets the help he needs before they can be in a healthy relationship, but they aren’t completely calling it quits just yet.”

Rumors that Disick and Kardashian were reconciling persisted, as evidenced by an Us Weekly report. “Scott is always going to be in love with Kourtney, and that’s something Sofia has had to face since even before she got serious with him,” a source told the outlet. “It’s been an ongoing thing. It just became more apparent that his family was more of a priority than she was, and his family would be his main priority over anything and anyone.” The insider added, “Sofia noticed that he wasn’t doing well and gave him an ultimatum, and in the end it seemed like Scott was more focused on Kourtney and his kids than her.”

June 2020

Speculation about the nature of Disick and Kardashian’s relationship followed them into June. Kardashian posted an Instagram of herself in Wyoming, wearing an oversized flannel shirt that seems to be Disick’s. He was photographed out wearing it before, a Kourtney fan account noticed, and it was while on a date with Sofia. The Sun has photos. Scott was also in tow for the family Wyoming trip, Us Weekly reports.

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Shortly after, a source told People Richie was hurt by the rumors and “still processing the breakup.” The insider explained, “It was a serious relationship, not some fling, and she was there for Scott through some tough times. It hurts to see all the speculation about Scott and Kourtney, but she is so young and gets so much attention. She’ll be totally fine.” People reported earlier that week that Disick and Kardashian were “not back together,” just “incredibly close.”

July 2020

Less than two months after their reported breakup, Richie and Disick reconciled, according to Us Weekly. That was a move predicted by E!’s source at the time of their May breakup. The Us source said, “they are hanging out again romantically. It’s back on.” The insider added, “They weren’t getting along before—hence the split, and they worked on having a life separate from each other.”

That report came after the pair was spotted together during the Fourth of July. Richie even posted a photo of herself at Disick’s house that month.

August 2020

Less than a month alter, E! reported Richie and Disick were together no longer. The news comes amid Kardashian and Disick’s family vacay with their kids and pals at Idaho’s Lake Coeur d’Alene. Their getaway breaks non-essential coronavirus travel guidelines once again, following outings in Utah and Wyoming over the summer. Kardashian posted a swimsuit shot of herself on a boat captioned, “lake ya.” Disick commented, “What a lake er.”

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E!’s source attributed Richie and Disick’s latest split to his spending a lot of time with Kardashian. “Things haven’t been great between them. Scott’s been spending every day with Kourtney and the kids and has been vacationing with her,” the source said. “Things are always tense between Scott and Sofia when he goes away without her.” The insider added that Disick had been spending a “majority” of his time with Kardashian and their children.

Disick and Kardashian went out to eat together at Nobu in Malibu on August 28, where Richie apparently ate just before they arrived.

Editorial Fellow Savannah Walsh is an Editorial Fellow at ELLE.com.

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