Kourtney Kardashian, Scott Disick 'and' Sofia Richie's Relationship Timeline

From the ins and outs of Kardashian and Disick's nearly 10-year romance to Disick and Richie's on-and-off-again status, here's everything you need to know

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Kourtney Kardashian and Scott Disick started dating in 2006 after meeting at Joe Francis' home in Mexico.

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Scott Disick and Kourtney Kardashian
Scott Disick and Kourtney Kardashian. Seth Browarnik/Startraks

Keeping Up with the Kardashians premiered in 2007 and Scott was introduced as Kourtney's boyfriend on season 1. Since then, the show has documented the pair's highest highs and lowest lows.

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Some of the lows have included Scott's drinking and partying; the sudden death of his parents, Bonnie and Jeffrey Disick; and Kourtney's struggle to open up about her feelings.

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scott disick family
Scott Disick and Kourtney Kardashian with their children. Instagram

The highs certainly include the births of their three children, Mason, Penelope and Reign.

Scott and Kourtney were together for nine years before she officially ended things in 2015.

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Kourtney Kardashian and Younes Bendjima enjoy a trip on Big Thunder Mountain at Disneyland Paris
Pacific Coast News

In 2017, Kourtney was seen hanging out with model Younes Bendjima. The two were first introduced during a trip to Paris in October 2016. It was the first time Scott had seen Kourtney with another man, so it was tough for him to accept that she was trying to move on. "Scott is a typical guy about it," a source told PEOPLE at the time. "He doesn't like that she is dating. For him, it's fine to hang out with girls, but when Kourtney does, he pouts."

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Sofia Richie and Scott Disick

At the same time, Scott was also seeing other women and had brief flings with Bella Thorne and stylist Chloe Bartoli before linking up with current on-again, off-again girlfriend Sofia Richie. Scott and Sofia were first seen cuddling aboard a yacht in Cannes in May 2017. At the time, the model denied any romance, tweeting, "Just so everyone can get their panties out of their a—es, Scott and I are just homies," adding the hashtag, #relax.

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Kourtney Kardashian and Younes Bendjima in love at the Eden Roc during the 70th Cannes Festival

While Scott was in Cannes with Sofia, Kourtney was also in Cannes with Younes. During a 2017 episode of KUWTK, Scott and Kim Kardashian West discussed what was really going on during the headline-making Cannes trip and how it made Scott feel to see Kourt with another man.

"It just looked like it was some big soap opera going on — it was like, a fun show," said Kim of the dueling paparazzi pictures that surfaced at the time.

"I didn't see the show, because I was living it," Scott said. "But look at it [from] my perspective: She was on vacation with one man, a whole trip. That looks like a happier scenario than me, jumping around trying to find happiness and these girls are not fulfilling that. I'm just not happy with anybody."

Scott went on to confess to Kim that he felt "insecure" about Kourtney potentially moving on. "Like, if Kourtney met someone, fell in love and got married and then everyone's like, 'Eh, we have a new Scott — we don't really need to be close with him anymore,' " he said. "Even though I get it — we have kids [together]. But it's a scary thing for me."

"My true advice would be let's cross that bridge when we get to it," said Kim, before giving him a hug and promising him "no judgment."

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Alec Monopoly/Instagram

By September 2017, Scott and Sofia went Instagram official. During a trip to Miami, Scott posted a picture of himself and Sofia on his Instagram story. In the photo, the two are posing together in front of a blue sky, with his face hiding behind hers. Sofia posted a similar photo on her Instagram story with the couple posing with their arms around each other. One of their friends also shared a video of Scott and Sofia kissing on the lips, seemingly sealing their relationship status.

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As for Kourtney and Younes, the two were happily moving forward and even rang in 2018 together. "It's definitely serious," a source close to the pair told PEOPLE at the time. "No one thought their relationship would last this long, but Kourtney is very happy."

"Younes has met her kids," the insider added. "It's obvious that he really cares about Kourtney."

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Andrew Toth/Getty.

Scott and Sofia were also getting more serious, taking trips to Miami, then Mexico and later Milan. Things seemed to be going well, but by November 2017, their relationship started to fizzle. "They're starting to argue more, and it's bothering Sofia," a source told PEOPLE. "She thought he would be more serious about their relationship and is finding herself to be more frustrated with him as time goes on... It's really upsetting for her, but she is trying to work through it."

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Scott Disick/Instagram.

However, shortly after, the two got back on track and entered 2018 as a couple. Things may have started looking up for Scott and Sofia, but Kourtney's family still had their reservations about their age gap.

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That January, Younes and Kourtney took a trip to Punta Mita, Mexico, for some rest and relaxation. The following month, Kourtney brought up the idea of freezing her eggs on an episode of KUWTK, she told sisters Kim and Khloé.

"Are you serious?" said Kim. "You want another kid?"

"I should just do it so I don't have to think, 'Is this what I want, to have kids?'" said Kourtney. "It's like, putting too much pressure."

Asked Kim, "Who would you have a kid with?"

Kourtney asserted, "I don't know," though she elaborated, "I'm saying if I am like in love and the person wants to have a kid."

"So you're thinking about a younger guy!" asserted Khloé, clearly alluding to Younes.

But in a turn of events, Kourtney admitted she wasn't opposed to expanding her family with Scott. "I feel like I would [have another baby with him] if the situation was right," she said. "But that doesn't mean, like, tomorrow, guys. So don't get any ideas."

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Meanwhile, Scott gifted Sofia a new fur baby in February 2018. At the Issey Miyake Launch Party at Milk Studios in L.A., Sofia told PEOPLE about how her new wiener dog got her name. "Her name's [Hershela]," she said, not specifying the exact spelling. "My boyfriend named her … I kind of just ran with it. It made me laugh. I liked Hershey and he liked Hershela, so it was like a middle ground."

"He wanted the dog for a while, but he ended up surprising me with it," she added.

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Younes Bendjima Instagram story screenshot 3/5/18.

In March 2018, Kourt caused a frenzy online when she briefly shut down her Instagram account, while Younes made his private, according to Cosmopolitan — just days after the couple reportedly unfollowed each other on the app. The model also posted a cryptic quote about disconnecting from social media, writing: "Feels good to stop looking at your phone and start looking at the world. Try. Even for a day."

But soon after, all was seemingly well between the two and both accounts were active once again and visible to the public. The couple also followed each other again, and a source told PEOPLE that "everything is fine."

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In March 2018, Sofia and Scott took another major step and went on a trip to Cabo with Scott's kids. "Scott, Sofia and his kids flew to Cabo San Lucas via private jet," a source told PEOPLE, who noted that the group stayed at the luxury Chilean Bay resort & residences. Sofia shared a photo of the couple boarding their private jet. "My [heart]," she captioned the shot.

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Kourtney Kardashian/Instagram.

Kourt and Younes did some traveling too. They went on a road trip along the coast of California in March 2018, jetted to Turks and Caicos in April and also took a plane to a secret destination for the then-25 year-old's surprise birthday trip in May. Amid all that traveling, the pair also had time to pose for a Calvin Klein ad on Instagram, confirming to fans that they were still going strong.

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By the time Sofia celebrated Scott's 35th birthday in May 2018, a source told PEOPLE that Kourtney had started to warm up to their relationship. "It helps that Kourtney now trusts Sofia," said the insider. "The kids are allowed to spend time with her. Sofia likes having them and helps Scott. So far, the kids are giving Kourtney good reports about Sofia."

"Sofia has shown over and over again that she is willing to stay with Scott even when things are not great — but Scott is doing well lately," added the source.

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Bryan Steffy/WireImage; Venturelli/WireImage for amfAR

However, in June 2018, Scott was spotted looking flirty with a mystery woman at Kanye West's Ye listening party in Jackson Hole, Wyoming. Scott reportedly told guests that he and Sofia were no longer together, according to TMZ. A source confirmed to PEOPLE at the time that Sofia had called it quits.

"Sofia broke up with Scott," said the insider, adding that Scott's "old issues" contributed to the split.

A second source added that Scott "cheated on her, and she confronted him."

As for how Scott was dealing with the breakup? "Scott seems fine," said the first source. "He even thinks she might change her mind. He isn't really taking it seriously."

The second source also speculated that "it's likely not totally over." "They've broken up multiple times since they started dating and always ended up back together," said the insider. "No one would be surprised if they're out again together in a few days or weeks."

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Scott Disick/Instagram.

Although multiple insiders said there was a good chance for a reconciliation, one source confirmed to PEOPLE that Sofia moved out of Scott's house after the breakup to stay with her dad, music icon Lionel Richie. "She has been living at Lionel's house for the past couple of days," said the source. "She is looking for her own place."

Then suddenly, the duo appeared to reconcile and were spotted together again.

Scott also publicly denied that the two had ever split, posting a screenshot on his Instagram story of a TMZ headline that read: "Sofia Richie & Scott Disick Still Together." "We had no idea we even broke up but thanks for thinking of us," he captioned the post.

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Kourtney Kardashian and Boyfriend Younes Bendjima are Spotted Having a Romantic Dinner in Rome, Italy.

In July 2018, Kourtney and Younes took a trip to Italy and were joined by her kids. "She is incredibly happy with Younes," a source told PEOPLE at the time. "They are getting serious. Younes is very close to her kids and loves spending time with them. The kids really like him."

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Shortly after their family vacation, Kourt broke up with Younes in August 2018, a source confirmed to PEOPLE, adding that "it didn't end well." Photos of Younes getting cozy with another woman in Mexico surfaced on TMZ. On his Instagram story, Younes denied the situation was romantic, writing: "They really want me to be the bad guy. F— your Hollywood bulls—, can't have fun with your friends no more." Just hours after photos surfaced, a source told PEOPLE, "Younes was always supposed to be a rebound. Now with the pictures of Younes in Mexico, [he and Kourtney] are definitely not getting back together."

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Swan Gallet/WWD/REX/Shutterstock; Tom Briglia/ WireImage

A source told PEOPLE in August 2018 that Scott "hated Younes" and was "happy things are over." "Seeing Kourtney date Younes definitely played into his partying," said the source of Scott. "He's never gotten over her and was really hoping to get her back when she first started dating Younes."

Scott had been dating Sofia at the time but according to the source, he would "get back together with Kourtney in a heartbeat." "Sofia makes him happy but they are also very on and off. It wouldn't be surprising if Scott tried to pursue things again with Kourtney down the line."

But a second source told PEOPLE that Kourt was "happy being single for now." "Kourtney is doing great," the source said at the time. "She isn't seeing Younes. After all the drama with Scott over the years, she wasn't going to put up with any drama from Younes. She cut him off. She is focused on her kids and herself."

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In late December 2018, Kourtney, Scott and Sofia surprised everyone by going on a vacation together with the kids in Cabo San Lucas, Mexico. Scott posted a photo of three with the cheeky caption, "What more can a guy ask for. THREE'S COMPANY."

Though the father of three sat between them in the photo he shared, the ladies lounged next to each other at one point, chatting and looking at Kourtney's phone. The ladies also walked on the beach together as Mason, Penelope and Reign played in the sand.

Khloé tweeted in response to a fan who called her sister's vacation "co-parenting done right!!" "Beyond proud of all of them!!!! This is LOVE!! Your children before anything else!! All amazing adults right right!!!" she tweeted.

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*EXCLUSIVE* Kourtney Kardashian takes on cold Aspen winds with see through top while out with Scott and Sofia

The trio seemed to hit it off and were spotted taking another trip, this time to Aspen, Colorado, in late December 2018.

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Kourtney Kardashian. Younes Bendjima/Instagram

Meanwhile, Younes reminisced about his favorite moments of 2018 on social media and gave his ex a shoutout. On his Instagram Story, the model praised Kourt, calling her "an amazing woman and mum." Alongside a photo that showed the mom of three sitting on a mattress outside at sunset, Younes wrote, "Let's not forget about this beautiful woman inside and out."

"I'm not the type of man that forget[s] moments like that," he added. "I hope you will find happiness for you and your childrens [sic]. It's all love at the end of the day. We don't know what can happen tmrw so there you go."

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In April 2019, Kourtney celebrated her 40th birthday alongside a few of her exes: Younes, Scott and Luka Sabbat. "When she talked about turning 40 awhile back, she didn't seem too excited," a source told PEOPLE at the time. "Turning 40 is a big deal. But instead of seeing it as something negative, Kourtney turned it around and she seems very excited about her life just in general."

"Kourtney likes having someone in her life. She loves being a mom and that's always her priority, but she can get lonely too," the source said. "She goes on dates and has fun, but she doesn't have a boyfriend and would never call any of these guys her 'boyfriend.' "

"She's been through a lot, personally, over the last decade and feels she's come out stronger and happier," continued the source. "So she's excited about turning 40 and what's to come."

"It hasn't been easy, but now she's in a great place with Scott," the source added.

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Jamie Nelson/Paper

In May 2019, Kourtney told Paper magazine that her amicable relationship with Scott and Sofia is "probably the thing I'm most proud of." Of her vacations with Scott, their three kids and Sofia, she said, "I don't think we'll go on every trip together, but I love that I'm invited."

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Kourtney Kardashian/Instagram; Daniele Venturelli/Getty

As things seemed to be going well for Kourtney, Scott and Sofia, mom Kris Jenner popped in to give her two cents on her fears about her daughter and Scott getting too close again. On a June 2019 episode of KUWTK, Kris, Kim and Khloé discussed the photo of Scott, Kourt and Sofia in Mexico. "To be honest, it's a little confusing," said Kris. "Kourtney and Scott and Sofia on vacation together — what is happening? Why in the world would she feel the need to go on vacation with Scott?"

Kim said her sister probably just wanted to spend time her kids, but Kris wasn't having it.

"She has a lot of trips with the kids. She can pick up and go to Mexico any day of the week," Kris said. "My fear is that she can't make up her mind. She can't pick a paint color! That takes months. I'm just saying, because of her indecisiveness, it's going to bite her in the a—. And she's going to be the one deciding way too late that she is in love with Scott and wants to spend the rest of her life with Scott."

"She doesn't know what the f— she wants," Khloé said.

"Exactly," Kris replied. "Somebody is going to end up getting really hurt in this scenario."

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Scott Disick and Kourtney Kardashian Clash While Soaking in Hot Tub with Sofia Richie on KUWTK

Despite Kris' concerns, the three continued to maintain a relationship. However, keeping the peace between all three took work. On an October 2019 episode of Keeping Up, Kourtney headed to Finland for spring break with Scott, their kids and Sofia.

"I was first going to go to Finland as a girl's trip, but it just seemed like a lot of the activities my kids would love. The dates that we were able to go ended up being spring break, and then Scott really wanted to come along," Kourtney explained to Khloé. "And then it was my idea to invite Sofia to come on our trip."

Once on the trip, Scott admitted he was struggling to make sure everyone felt comfortable. Though Sofia and Kourtney seemed to be bonding, he was nervous about Sofia's feelings. "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," he said. "Tons of people walking around that Kourtney and I have known for over 10 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."

He continued: "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. 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."

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Kourtney Kardashian
FIA Pictures

Once they got back to L.A., Kourtney seemed to be hanging with a friendly ex. She and Younes were spotted holding hands, hanging out at Miami Art Basel and reuniting at Disneyland — all while denying dating rumors.

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Kourtney Kardashian & Younes Bendjima
Kourtney Kardashian and Younes Bendjima. Kourtney Kardashian/ Instagram

By Christmas 2019, a source confirmed to PEOPLE that Kourt and Younes were dating again. A second source added that "Kourtney decided to give him another chance."

"They have fun together and her kids like him," said the second source. "He seems very committed to Kourtney. She's happy that they are back together. She didn't want to hide the relationship anymore. It was her decision to make it public again."

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Sofia Richie and Scott Disick
Sofia Richie and Scott Disick. Sofia Richie/Instagram

In February 2020, Scott and Sofia had surpassed two years together but not without a few breakups and makeups. A source told PEOPLE at the time that there is often "some kind of drama" with the pair. "Scott and Sofia are the type of couple that constantly split up and get back together," the source said. "It's all very dramatic, and then all good again."

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Scott Disick Seen for first time since leaving rehab and breakup with Sofia Richie

By the spring of 2020, the world was dealing with the coronavirus (COVID-19) pandemic, Kourtney and Younes had seemingly fizzled, and, in May, Scott checked himself into rehab, a source confirmed to PEOPLE. "Scott entered a treatment facility last week," the source said. "He knew he was spiraling out of control and wanted to get help. He wants to be the best dad possible. Sofia [Richie] and Kourtney [Kardashian] both encouraged him to get help."

The star's attorney Marty Singer denied that Scott sought treatment because of cocaine and alcohol. "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," Singer said in a statement to PEOPLE.

Another source told PEOPLE that Sofia "is very supportive." "They reunited at Scott's house after he returned to L.A.," the source said. "Sofia still lives with him. Scott is very happy to have Sofia by his side."

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Sofia Richie and Scott Disick. Romain Maurice/Getty Images for Haute Living

But by the end of May 2020, a source told PEOPLE that Scott and Sofia were "taking a break right now so Scott can just focus on the most important things in his life — his health and his kids."

"Scott is working on his issues. Sofia is hanging out with friends," the source explained. "It was Sofia's choice to take a break."

A second insider also confirmed they went on a break. Reps for the stars have not commented.

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Kourtney Kardashian, Scott Disick
Kourtney Kardashian, Scott Disick. Charles Sykes/Bravo/NBCU Photo Bank/NBCUniversal via Getty;

During Sofia and Scott's break, a source told PEOPLE in June 2020 that Kourtney and Scott were "not back together" but "are incredibly close."

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NO REUSE Scott Disick Sofia Richie

While Scott was working on himself after rehab and keeping a strong relationship with Kourtney, Sofia was "still processing the breakup," a source told PEOPLE in late June 2020. "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."

A rep for Sofia did not respond to PEOPLE's request for comment. But by July 2020, Scott and Sofia were spotted together again.

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Scott Disick, Sofia Richie
Scott Disick and Sofia Richie. Denise Truscello/Getty

In July 2020, the two were "trying to make things work while taking things slow," a source told PEOPLE.

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Sofia Richie and Scott Disick shopping

By August 2020, the couple called it quits again. "It's always been difficult for them to balance their relationship with Scott's family life," a source told PEOPLE on Aug. 20. "His kids will always come first."

A second source told PEOPLE the two "are not seeing each other." "Scott's focus is his health and the kids," said the source. "Sofia wants to hang out with friends and enjoy the summer. Since they are no longer on the same page, they decided to just be apart. At least for now."

Reps for Disick and Richie did not immediately respond to PEOPLE's request for comment.

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Disick used son Mason and Reign's joint Dec. 14 birthdays to shout out Kardashian.

"Thank you @kourtneykardash for being the best baby maker in town, I couldn't have asked for a better person in the world to have these amazing children with, I love u and our family more than anything in the world," he wrote, sparking comments like "Just get back together already" on the post.

The praise came one month after the former pair joked about going for baby No. 4 on an episode of Keeping Up with the Kardashians.

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