Scott Disick and Kimberly Stewart's Relationship Through the Years

Friends first! Scott Disick and Kimberly Stewart go way back — they knew each other for more than a decade before they started dating.

Before she met the Flip It Like Disick alum, however, the model was initially close with his ex-girlfriend, Kourtney Kardashian. Stewart — who is the daughter of rocker Rod Stewart — and the Poosh founder grew up together in Los Angeles.

Kimberly’s mother, Alana Stewart, has claimed that her daughter is actually responsible for setting up Disick and Kardashian in 2006, with help from her little brother Sean Stewart. The Talentless designer and the Keeping Up With the Kardashians alum — who share sons Mason (born December 2009) and Reign (born December 2014) and daughter Penelope (born July 2012) — dated off and on until 2015.

“They introduced Scott to Kourtney,” Alana told People of Kimberly and Sean in September 2015. “I was there when it happened, so I can tell you they’re all great pals.”

Kimberly and Disick remained friendly throughout his relationship with Kardashian, and they were occasionally photographed hanging out together in Miami and New York City. It wasn’t until 2015, though, that romance rumors started brewing.

After the New York native and the Hulu personality called it quits, Us Weekly reported that Disick and Kimberly hooked up several times. “It was going on for several weeks,” an insider said at the time. (A rep for the Stewarts & Hamiltons alum denied the report.)

Disick went on to date a string of women including Sofia Richie and Amelia Gray Hamlin, but he remained close with Kimberly. In August 2022, Us confirmed that the duo had started dating “a few months” earlier.

They’re “really into each other,” an insider told Us at the time. A second source noted that the pair had known each other for “years” after meeting through Kimberly’s brother Sean. “They had the same friend group and hung out in the same circle,” the second insider told Us, adding that the couple intentionally waited a while before going public with their romance.

“They’re just getting to know each other in a different way than seeing each other as friends,” the source explained.

Disick was previously linked to Rebecca Donaldson in early 2022, but the pair called it quits in June after two months together. Kimberly, for her part, previously dated Jesse Shapira and Cisco Adler. The Los Angeles native shares daughter Delilah, born in August 2011, with Benicio del Toro.

Keep scrolling for a look back at Disick and Kimberly’s history through the years.