The Flip It Like Disick star was first seen cozying up to the model, who is 16 years his junior, during a fun-filled getaway to the South of France in May 2017. Four months later, Us Weekly confirmed that the flirty pair were hooking up. “Things became official over the past week while they were in New York City together,” a source explained at the time. “It’s so weird. Not just the age difference, but mostly the fact that Sofia had been a family friend for years, and was close to Kendall and Kylie [Jenner].”
Before heating things up with Richie, Disick was in a longtime on-off relationship with Kourtney Kardashian, with whom he shares children Mason, Penelope and Reign. For years, fans watched the former pair’s drama play out on Keeping Up With the Kardashians until they called it quits once and for all in 2015 after nine years together. Despite her own ups and downs with her ex, the Poosh founder gave Richie her full stamp of approval.
“Kourtney thinks Sofia brings out the best in Scott and is happy for them,” a source revealed in September 2019. “Kourtney and Sofia share a common background and lifestyle, and Sofia is easy to get along with and is a normal girl.”
Though they may have seemed like a perfect fit, Us confirmed that Disick and Richie called it quits in May 2020 after the reality star’s brief stay in a Colorado rehab facility.
“Sofia and Scott breaking up was only a matter of time. Scott isn’t the best version of himself right now and it has been a lot for Sofia,” a source explained at the time. “[Sofia] is sad about the situation, but trying to take care of herself.”
Disick, for his part, was “feeling sad and defeated in a way right now and upset about all the news surrounding his relationship before his split.”
In July 2020, the pair appeared to be back on yet again. However, Us confirmed in mid-August 2020 that the pair were on another break and “spending time apart.”
Scroll down to relive Disick and Richie’s romance: