Kourtney Kardashian and Scott Disick's Relationship Timeline

Kourtney Kardashian and Scott Disick dated on and off until 2015 and share three children together

Keeping up with Kourtney Kardashian and Scott Disick's relationship hasn't always been easy.

Since meeting in 2006, the former couple have had their ups and downs — the majority of which were chronicled on Keeping Up With the Kardashians and its multiple spin-offs. Kardashian and Disick dated on and off until 2015. During that time, they welcomed three children together: Mason Dash, Penelope Scotland and Reign Aston.

The exes have remained friendly co-parents, even after Kardashian wed Travis Barker in May 2022.

"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 or not," the reality star said previously on an episode of KUWTK.

Kris Jenner confirmed Disick's place in her family on an episode of The Kardashians in 2023.

"I love Scott and we all love Scott," Jenner said after Discick was in a horrific car crash. "And Scott will always be a part of our family. He's the father of my grandchildren and he's just ... my kid."

From their early days on reality television to their current status as co-parents and cordial exes, here is a complete look at Kourtney Kardashian and Scott Disick's relationship.

2006: Kourtney Kardashian meets Scott Disick in Mexico at Joe Francis' house

Kourtney Kardashian, Scott Disick, and friends
Kourtney Kardashian Instagram

Kardashian met New York-native Disick at a gathering at their mutual friend Joe Francis' home in Mexico in 2006. Kardashian later shared a photo from that night on her Instagram account, showing the two of them sitting at opposite ends of a couch with friends and Francis in between.

On a later episode of Kourtney & Khloé Take the Hamptons, Kardashian admitted that their meeting was not love at first sight.

"I liked her," Disick said. "But she wanted nothing to do with me."

"I just thought he was so annoying," Kardashian said of their first encounter. "He was four years younger, he lived in New York, he didn't have a job."

October 14, 2007: Scott Disick appears on the series premiere of Keeping Up With the Kardashians as Kourtney Kardashian's boyfriend

In the first episode of Keeping Up With the Kardashians, Kardashian introduced Disick to the public as her boyfriend. "We were friends for about a year and then started dating, and have been together ever since," she said in the premiere.

However, Kardashian's mother Kris expressed her doubts about Disick's maturity and fidelity. "I have serious doubts about Scott," Kirs said in the episode. "I found out he's cheating on Kourtney and as her mom, I want to tell her but I don't know how."

Kris later confronted Disick about whether he was ready for a serious relationship with her eldest daughter. "To me, he's really young and I just don't see somebody his age settling down into that kind of life right now," she said of the then-24-year-old.

Disick, however, expressed his love and commitment to Kardashian. "I love her to death," he said. "I will never do anything to disrespect your daughter."

November 18, 2007: Kourtney Kardashian and Scott Disick almost marry in Las Vegas

On an episode of Keeping Up With the Kardashians, Disick asked Kardashian if she wanted to marry him after a night partying in Las Vegas.

"Would you hate it if I asked you to marry me right now, or tomorrow?" he asked as they headed back to their hotel room. "I've never wanted to do anything more."

Kardashian initially agreed, and the couple went as far as going to the Little White Chapel with sisters Khloé and Kim and mom Kris in tow. But Kris talked Kardashian out of the Vegas wedding before the two could walk down the aisle.

"This feels wrong," Kris said to Kardashian. "You're rushing it."

Kardashian and Disick agreed to put a stop to their Vegas nuptials. "I guess Scott and I will just keep living in sin," Kardashian said in the episode.

March 9, 2008: Kourtney Kardashian and Scott Disick split for the first time

Kourtney Kardashian, Scott Disick
Kourtney Kardashian and Scott Disick. Denise Truscello/WireImage

Kardashian and her sisters Kim and Khloé discovered text messages on an old phone of Disick's from someone named "my wife." The texts lead the reality star to believe Disick had cheated on her while in the Hamptons, and she confronted him on the season two premiere of Keeping Up With the Kardashians.

"I cannot believe Scott could have cheated on me. I'm sick to my stomach that this could have happened," Kardashian said on the episode.

The two split soon after. "Unless you can be honest, I have no reason to talk to you again," Kardashian said to Disick at the time.

August 13, 2009: Kourtney Kardashian reveals she is expecting her first child with Scott Disick

Kardashian confirmed she was expecting her first child with Scott Disick just days before her spin-off Kourtney and Khloé Take Miami premiered on E!.

"We were in the Everglades, and I kept feeling nauseous and sick. I just kept thinking something wasn't feeling right," she said. "I've never missed a period in my life. Literally, I took like 20 tests; I went to the doctor and he confirmed the news. I was just so shocked."

Kardashian later revealed that the unplanned pregnancy was the result of a fling with her ex Disick. The two had since reconciled, but the reality television star was still anxious to tell her family about the pregnancy — since their distrust of Disick had been chronicled on Keeping Up With the Kardashians. She also spoke to PEOPLE about how she and Disick agonized initially over whether to keep the baby.

"I felt in my body, this is meant to be," she said. "God does things for a reason, and I just felt like it was the right thing that was happening in my life."

December 14, 2009: Kourtney Kardashian and Scott Disick welcome their first baby

Kardashian and Disick became first-time parents when the reality star gave birth to a healthy baby boy named Mason Dash Disick. Weighing in at 7 lbs., 6 oz., the first Kardashian grandchild was born nine days ahead of his Dec. 23 due date.

Kardashian infamously pulled out Mason herself during the birth, which was later featured on an episode of Keeping Up With the Kardashians. Not only were cameras present, but so were her sisters Khloé and Kim, and her mom Kris.

"​​The experience was so indescribable and life-changing, and I can't believe he's all mine," Kardashian said at the time.

"It's honestly like a little piece of me was just reborn," added Disick. "And I'm so happy I'm here with Kourtney."

August 2010: Kourtney Kardashian and Scott Disick split again — but later reconcile

Scott Disick and Kourtney Kardashian attend Jet Nightclub at The Mirage on February 19, 2010 in Las Vegas, Nevada
Denise Truscello/WireImage

In an episode of season two of Kourtney and Kim Take Miami, Kardashian breaks things off with Disick for a second time after a night of drinking leads to him punching a mirror.

"I don't know where this crazy anger comes from," Kardashian said in the episode. "He gets this crazy rage inside of him that's not okay."

She later told Disick their relationship was over until he got help for his drinking and anger. "You're not going to be around Mason while you're working on yourself," she said in the episode. "I can't do this s--- anymore. I love Mason more than I love you and that's what it is."

Days after the episode aired, Kris revealed at a press event for Keeping Up With the Kardashians that the couple was "really trying to work on their relationship." A rep for the show confirmed Kardashian and Disick were in couples therapy, and Disick was abstaining from drinking.

"Scott is really trying to work on himself," Kris said. "Scott has really stepped up to the plate. It's been amazing."

April 2011: Scott Disick considers proposing to Kourtney Kardashian

On the season one finale of Kourtney and Kim Take New York, Disick planned to propose to Kardashian while celebrating their anniversary. However, he never got the chance — since Kardashian revealed she was content with their life as a family of three.

"Things are so good now and we have finally come to this place, why would we want to change that," Kardashian said in the episode. "I just feel like right now I'm pretty happy with the way things are."

Though Disick never went through with the proposal, the couple and baby Mason did move in together upon returning to California.

November 30, 2011: Kourtney Kardashian and Scott Disick announce they're expecting their second child

Scott Disick and TV personality Kourtney Kardashian arrive at the Taste Of Beverly Hills held at The Beverly Hilton hotel on September 2, 2010 in Beverly Hills, California
Barry King/FilmMagic

Nearly two years after welcoming son Mason, Kardashian and Disick revealed that baby number two was on the way.

"It's soooo exciting!" Kim Kardashian told PEOPLE about her sister's pregnancy news. "They are so happy and so am I!"

July 8, 2012: Kourtney Kardashian gives birth to her second baby, a girl, with Scott Disick

Kardashian and Disick welcomed their second child, a daughter named Penelope Scotland, at Cedars-Sinai Medical Center in Los Angeles. The baby girl weighed 7 lbs., 14 oz. and was delivered via an all-natural birth.

"Scott and I are overjoyed to welcome our precious angel Penelope Scotland Disick into our lives. We are forever blessed. Mommy and baby are resting comfortably," Kardashian said in a statement.

It was another easy delivery for Kardashian, according to Kris. "It was great," the Kardashian matriarch said. "[Penelope] is so cute. She looks just like Mason. She's so beautiful. We are so happy."

June 4, 2014: Kourtney Kardashian and Scott Disick are expecting baby number three

PEOPLE confirmed Kardashian was pregnant with her third child shortly before filming began on the family's new series, Kourtney and Khloé Take the Hamptons.

"She's really excited but she's nervous too," a source told PEOPLE. "Three kids is a lot to handle! But she's happy — she's always wanted a big family with Scott."

The news of the pregnancy came months after Disick lost both of his parents three months apart. "It has been a tough time, and, you know, just like anyone who has been through something tough, I just have to think about the positive things and hope for the best," Disick told PEOPLE.

December 14, 2014: Kourtney Kardashian and Scott Disick welcome a second baby boy

Scott Disick Celebrates His Birthday at 1 OAK Nightclub Las Vegas at The Mirage Hotel & Casino
Scott Disick and Kourtney Kardashian in May 2015. David Becker/WireImage

And baby boy makes five: The couple welcomed their third child, son Reign Aston Disick, on Dec. 14 — the same day big brother Mason turned five.

Kardashian shared a photo to Instagram of her holding baby Reign's hand. "Madly in love with my little Reign Aston Disick," she wrote.

And though Reign arrived on Mason's birthday, Kardashian made sure her eldest son still got a special birthday celebration. The reality star threw him a Nightmare Before Christmas-themed party in November before Reign's arrival.

March 16, 2015: Scott Disick enters rehab with Kourtney Kardashian's support

Disick checked in to Rythmia Life Advancement Center (RLAC) in Costa Rica, PEOPLE confirmed. The rehabilitation center specializes in alternative therapy and the reality star participated in iboga treatment, which uses a special African plant to cure addiction, a statement revealed.

"I realize my issues are bigger than me and I'm ready to truly remedy this struggle I continue to battle," Disick said in the statement.

Kardashian stood by Disick during his rehab stay. "He is doing well. I think the thing that's most important to me is just his commitment to working on himself," she told PEOPLE. "If somebody doesn't want to make changes then that's really hard."

She continued, "He is learning so much about himself and growing, and so that's really amazing to see. When he's working on himself it only betters our relationship."

July 2015: Kourtney Kardashian ends her relationship with Scott Disick amid cheating allegations

After nine years and three children together, Kardashian ended her on-again, off-again relationship with Disick after photos emerged of him cozying up to stylist Chloe Bartoli in France. The split was later featured on an episode of Keeping Up With the Kardashians.

"I'm literally on the verge of a mental breakdown," Kardashian said in the episode. "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 added, "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."

October 14, 2015: Scott Disick checks himself into rehab following his split from Kourtney Kardashian

Kourtney Kardashian and Scott Disick attend the RLife live launch event at Renaissance New York Times Square on October 28, 2010 in New York, City
Jamie McCarthy/WireImage

Disick checked himself into rehab on the heels of his breakup with Kardashian. The father-of-three sought help at Cliffside Malibu, a luxury drug and alcohol rehabilitation center, PEOPLE confirmed.

The decision to seek help came after receiving an ultimatum from Kardashian about being able to see their three children. Kardashian was reportedly considering seeking sole custody of the kids.

"He wants to make it stick this time because he has come close to losing everything," a source told PEOPLE.

March 28, 2016: Kourtney Kardashian and Scott Disick tease on Snapchat that they're getting back together

Disick and Kardashian teased a romantic reunion on his Snapchat account: "Hey, so, we wanted you guys to hear it first. We are getting back together," Disick said in the video, as he went in for a kiss on Kardashian's head. She laughed in response, saying, "No."

Though the couple was joking about getting back together, they had been spending time together as a family in recent weeks. On March 19, they were spotted taking their two oldest children, Mason and Penelope, to "The Wizarding World of Harry Potter" at Universal Studios Hollywood.

"By the way everyone relax, people that have three kids together spend time together," Kardashian said in a previous Snapchat video.

Despite his social media posts, Disick also dispelled any reconciliation rumors: "In the end, I'm trying to live my life. I'm trying to live it healthy. I'm trying to be there for the people I love, which is Kourtney and kids but you know what, we're not together," he told PEOPLE.

April 18, 2016: Scott Disick wishes his ex Kourtney Kardashian a happy birthday with an Instagram throwback

Kourtney Kardashian and Scott Disick
Kourtney Kardashian Instagram

Disick wished the mother of his three children a happy 37th birthday by posting a PDA-filled throwback photo to his Instagram account. The snap showed the pair sharing an embrace and kissing in the middle of the water.

"Happy birthday @kourtneykardash everyone who knows you loves you so much!" Disick captioned the photo, which was taken in 2009.

A month later, on May 28, Kardashian sent Disick happy birthday wishes with a throwback pic of her own.

"Happy birthday baby daddy!" she wrote alongside a photo of the two from when they were still dating.

November 13, 2016: Kourtney Kardashian and Scott Disick travel to Mexico together — and are reportedly living together again

Scott Disick and Kourtney Kardashian (R) celebrate Kourtney's birthday at the grand opening of Gallery Nightclub at Planet Hollywood on April 15, 2011 in Las Vegas, Nevada
Denise Truscello/Getty

More than a year after their split, Kardashian and Disick were spotted vacationing in Cabo San Lucas, Mexico.

"Scott set it all up and [it] was a way to try and make things work again with Kourtney," a source told PEOPLE. "He surprised her and whisked her away on this trip."

Disick shared photos from the trip on his Instagram account, captioning a photo of Kardashian in a thong bathing suit with "views."

In addition to vacationing together, sources also told PEOPLE that the friendly exes were living together again. An insider shared that Kardashian "seems very happy" with Disick, and another insider confirmed that Kardashian "definitely wants four kids." But in her October 2016 Cosmopolitan cover story, Kardashian was more coy about a possible reunion with Disick.

"The idea of having my family together is amazing, but it's not the way things ended up. They may end up there. I'm not sure," she said. "To me, it's in God's hands. If it's meant to be, then things will line up."

March 19, 2017: Scott Disick talks about "smooth" co-parenting with Kourtney Kardashian

Kourtney Kardashian and Scott Disick
Kourtney Kardashian Instagram

Following their October 2015 split, Disick and Kardashian continued to successfully co-parent their three children together. When asked about the secret to their parenting partnership, Disick opened up to PEOPLE.

"I don't want to jinx it," he said to PEOPLE. "I don't think we know any other way, to be honest. We never had any negativity between us and we made a very smooth transition into the way we live, and luckily, thank God, we're able to see one another and still be with our children and, knock on wood, that we have that. Thank God we have that and everyone is somewhat happy and it seems to work. It's not broke, so don't fix it."

A month later, in April 2017, Kardashian posted about their co-parenting on her Instagram account.

"MOM and DAD back at it again with the coparenting skills," she wrote alongside a photo of the two on a family vacation in Hawaii.

August 2, 2018: Kourtney Kardashian says Scott Disick will "always be family"

Though Kardashian and Disick had both moved on to other relationships — Kardashian with boyfriend Younes Bendjima and Disick with girlfriend Sofia Richie — the former couple will always be family, according to Kardashian.

"I think Scott will always be family, and so we really try to have a good relationship for the kids," Kardashian told PEOPLE. "We really do our best to make the kids the priority."

May 23, 2019: Kourtney Kardashian opens up about her relationship with Scott Disick and his girlfriend Sofia Richie

In the May 2019 cover story of Paper magazine, Kardashian shared that her amicable relationship with Disick and his girlfriend Richie was "probably the thing I'm most proud of."

The trio traveled together frequently with Kardashian and Disick's three children, visiting Cabo San Lucas, Mexico in December 2018 and Finland in April 2019. "I don't think we'll go on every trip together, but I love that I'm invited," Kardashian told the magazine.

A source previously confirmed to PEOPLE that Richie, Disick and Kardashian get along perfectly well.

"As much as people would love there to be, there isn't any drama between Scott, Sofia and Kourtney," the insider said. "They spend a ton of time together, and Kourtney is comfortable with Sofia around the kids."

June 22, 2020: Kourtney Kardashian wishes Scott Disick a happy Father's Day

Scott Disick (R) Celebrates Birthday with Kourtney Kardashian (L) at Gallery Nightclub at Planet Hollywood on May 27, 2011 in Las Vegas, Nevada
Denise Truscello/WireImage

Kardashian shared a special Father's Day tribute on Instagram to Disick, the father of her three children.

"Happy Father's Day, thankful for you and these three special ones," Kardashian wrote alongside a family pic.

Despite the sweet message and the exes spending more time together in recent months (including traveling to Amangiri in Utah in May 2020), a source told PEOPLE that Kardashian and Disick were "not back together" — but "are incredibly close."

December 14, 2020: Scott Disick calls Kourtney Kardashian the "best baby maker in town"

Kourtney Kardashian and Scott Disick with their kids
Scott Disick Instagram

Disick paid tribute to the mother of his three children in an Instagram post shared on Mason and Reign's birthday. Disick expressed his appreciation for his ex alongside a photo of the pair with Reign and daughter Penelope posing on a staircase.

"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," Disick addressed Kardashian.

"I love u and our family more than anything in the world 🌎," he added.

April 18, 2021: Scott Disick wishes Kourtney Kardashian a happy 42nd birthday, calling her the "best mom"

In honor of Kardashian's 42nd birthday, Disick posted a photo with the star and their three children. "Happy Birthday 2 the best mom a child could ask for and more!" he captioned the snap on his Instagram Story.

The post came as Disick was reportedly "struggling" with Kardashian's new relationship with Travis Barker. (The pair started dating in January 2021.)

"Scott was pretty shocked when he found out that they are dating, and he can tell that they have moved very quickly," a source told PEOPLE. "His kids love Travis, which is also hard for Scott. Kourtney and Travis are like a family with the kids. Scott is having a hard time with this situation."

June 18, 2021: Kourtney Kardashian denies ever hooking up with Scott Disick since their 2015 split

In a Housewives-style Keeping Up With the Kardashians reunion hosted by Andy Cohen, Kardashian was asked by the Bravo host if she and Disick had ever slept together since their split in July 2015.

"People cannot believe that, but we have not," Kardashian said at the reunion. "For real."

"We're great friends and co-parents," she continued, to which Disick added, "I mean, we're family. I think we always will be."

The former couple also gave their blessings to each other's current relationships (Kardashian's now-husband Barker and Disick's then-girlfriend Amelia Hamlin). "I think if you really love somebody, you want them to be happy no matter what. So I do give her a blessing to be happy," Disick said.

"Whoever would make him happy, I would give my blessing," Kardashian added.

October 20, 2021: Scott Disick distances himself from the Kardashians to process Kourtney Kardashian's engagement to Travis Barker

Scott Disick (L) and Kourtney Kardashian appear at 1 OAK Nightclub at The Mirage Hotel & Casino on February 21, 2015 in Las Vegas, Nevada
David Becker/WireImage

Following Kardashian's engagement to Barker, Disick reportedly needed to distance himself from the famous family to "make his peace" with the marriage proposal.

"He understands that it's not Kourtney's job or Travis's job to make him okay with this," a source told PEOPLE. "It's his job, and if he's going to co-parent with Kourtney, which he has been, he has to process this and make his peace with it."

"It's not about them, it's not about Kourtney," the source added. "It's about him needing some time to process this and deal with it on his own, without them. He'll come around soon."

April 14, 2022: Scott Disick opens up about losing Kourtney Kardashian as his "best friend"

On the premiere episode of the Hulu series The Kardashians, Disick shared that he and Kourtney have not been as close since she started her relationship with Barker.

"It was a huge adjustment losing Kourtney romantically, but now it's becoming a huge adjustment losing her as a best friend. Now we're really just more co-parenters. I'd say it's probably one of the more difficult things in my life," Disick said.

Despite that, Disick still had well wishes for the couple. "I understand what the bigger picture is," he said. "She's in a real thing and I believe that's true."

May 25, 2022: Kourtney Kardashian marries Travis Barker — and Scott Disick doesn't "handle it well"

Kardashian and Barker tied the knot in a lavish ceremony in Italy in May 2022. While Kardashian and Disick's three children were in attendance, the Talentless designer was not, and he reportedly did not handle the rejection well.

"Scott isn't taking this well. He's spending time with friends ... to keep his mind off of it," a source told PEOPLE exclusively. "It's been hard for him to process and digest even though he knew it was coming."

The source continued: "He was always accepted by the family, even at his absolute lows, and now he can't even come to one of the biggest events of the family. He's not handling it well."

August 28, 2022: Kris Jenner defends Scott Disick after reports he's been "excommunicated" from the family

After an outlet reported that Disick had been excluded from the Kardashian-Jenner family, Kris responded to the rumors on Instagram.

"Scott will NEVER be excommunicated from our family….," she wrote in the comment section of the post reporting the news. "He's the father of my grandchildren and a special part of our family…."

"We love him and not true! 🥰😍," she added.

December 17, 2022: Kourtney Kardashian and Scott Disick celebrate their son Mason's Bar Mitzvah

Kardashian and Disick hosted a private Bar Mitzvah ceremony for their son, Mason. The event was followed by a dinner and reception at offsunset, a Sunset Strip nightclub in West Hollywood.

A source said that the religious milestone was important to Disick, who was raised Jewish.

September 13, 2023: Source says Scott Disick and Kourtney Kardashian are "not as friendly as they used to be"

Kourtney Kardashian and Scott Disick
Jon Kopaloff/FilmMagic; ZAK BENNETT/AFP via Getty

Disick and Kardashian's relationship has evolved. A source told Entertainment Tonight that the Talentless founder and the reality star "are not as friendly as they used to be."

The insider added: "He tries to be respectful and give her space, while also being there for her and the family."

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