Scott Disick has had his fair share of high-profile relationships.
Kardashian and Disick were on and off for 10 years before ultimately ending their relationship in 2015. During a 2017 episode of KUWTK, Kardashian and her sisters Kim and Khloé confronted him for secretly inviting a woman on their family trip to Costa Rica.
"It's been nonsense for 10 years, like up and down, so this is like the final door closed. We're done," Kourtney said.
Here's a look back at Scott Disick's dating history.
Disick first met Kourtney at a party in Mexico in 2006, which was thrown by the creator of Girls Gone Wild Joe Francis.
"The night I met @letthelordbewith you," Kourtney captioned an Instagram photo shared in March 2015.
While she reminisced over the night they met, Kourtney admitted on a 2014 episode of Kourtney & Khloé Take the Hamptons that it wasn't exactly love at first sight.
"I liked her," Disick remembered. "But she wanted nothing to do with me."
"I just thought he was so annoying," she explained. "He was four years younger, he lived in New York, he didn't have a job."
Disick added with a laugh, "Three kids later, still no job, still no idea where it's going."
While they remained close for many years since the split, Scott has opened up about growing apart from Kourtney as her relationship with now-husband Travis Barker grew stronger.
"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 told Khloé Kardashian during a season one episode of The Kardashians.
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Stylist Chloe Bartoli and Disick reportedly dated in 2006 before he got serious with Kardashian. However, in 2015, the pair were linked once again after photos surfaced of them snuggled up in the South of France.
Christine Burke Instagram
Disick was briefly linked to model Christine Burke in 2016. Their rumored romance turned heads when people began to notice the similarities between Burke and Kardashian's younger sister, Kendall Jenner.
Disick and Burke were previously spotted in Calabasas, California, together in March 2016 and were later seen kissing on a yacht in Cannes, France — just weeks after he told PEOPLE he was single. The fling didn't last long, however.
Megan Blake Irwin
In 2016, Disick was seen with Australian model Megan Blake Irwin — who's eight years his junior — on multiple occasions. They were first pictured at Cipriani's in New York City in April 2016 and were seen leaving Nobu restaurant in Malibu, California, together.
In early 2017, Disick was spotted kissing and cuddling model Jessica Harris in a swimming pool during a trip to Miami.
In May 2017, Disick was linked to Bella Thorne, who is 14 years younger than him.
The pair appeared to be getting closer in Cannes, however, Thorne left just a few days into their trip.
"Scott is really nice, sweet, charming. I don't drink, and he really drinks a lot. And it just ended up ... I just wasn't down. I was like, 'I gotta leave.' We were [at Cannes] a day and a half before I was like I'm booking my flight and leaving," Thorne told Complex in June 2017. "I love to go out and have fun, I love to f------ dance, but I just don't party hardcore like that and it was way too much for me. I was like, 'Woah, this is not the way I live my life, bruh.' "
Disick and Thorne reunited the following month in California as they were seen leaving Lana Del Ray's birthday party. In July 2017, the actress revealed that she was still friends with Disick, but clarified she "was never with him sexually."
Disick and Sofia Richie had an on-off relationship for more than three years.
The couple were first spotted 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 #relax."
By September 2017, however, Disick and Richie had gone Instagram official. During a trip to Miami, Disick posted a picture of himself and Richie on his Instagram Story. In the photo, the two are posing together in front of a blue sky, with his face hiding behind hers. Richie posted a similar photo on her Instagram Story of 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 confirming their relationship status.
After a brief breakup in late 2017, Disick and Richie took another step in their romance and went on a trip to Cabo with Disick's kids. By May 2018, Kardashian had started warming up to the relationship, trusting Richie with Mason, Penelope and Reign.
"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," a source told PEOPLE at the time.
However, the couple officially parted ways in mid 2020.
Bella Banos Instagram
Disick was spotted briefly with model Bella Banos in October 2020, but they "weren't dating."
A source told PEOPLE at the time, "He has been on dates but isn't dating anyone."
"He's been telling friends how much she means to him and how into her he is," said the source.
The couple were pretty open about their relationship, often sharing loved-up Instagram posts.
To mark her 20th birthday in June 2021, Hamlin posted a series of Instagram Stories from an evening out in Miami, which included lavish gifts and PDA with Disick. In one video, Disick could be seen gifting his girlfriend a cross necklace by placing it around her neck, which prompted Hamlin to tear up and then thank Disick with a kiss on the lips.
However, not everyone was on board with the relationship. In an August 2021 episode of The Real Housewives of Beverly Hills, Rinna took a swipe at her daughter's boyfriend. While she said she could see her older daughter Delilah getting married in the future, she had different feelings about Amelia.
"I can't say the same for Amelia at this point," she mused. "No. Like, why can't it be Harry Styles? Why the f--- is it Scott Disick?"
In September 2021, a source told PEOPLE that the couple were going through a rocky patch. The same month, they officially called it quits, with an insider confirming to PEOPLE that Hamlin had broken up with Disick.
The reality star had a brief romance with Scottish model Rebecca Donaldson in early 2022. They made their red carpet debut at Hulu's The Kardashians premiere on April 7, 2022, and held hands as they posed for photos.