See a Breakdown of Scott Disick’s Complicated Dating History: Kourtney Kardashian, Sofia Richie and More

When it comes to A-listers with complicated love lives, Scott Disick definitely comes to mind. While he is primarily linked to on-again, off-again girlfriend Sofia Richie, as well as ex Kourtney Kardashian, the longtime Keeping Up With the Kardashians star has had a handful of other romantic relationships in between.

Scott’s dating history also includes actress Bella Thorne, celebrity stylist Chloe Bartoli and model Bella Banos. That said, the Talentless founder can’t ever seem to shake his feelings for Sofia. Since their relationship officially began in September 2017, the pair has split a number of times.

On May 21, 2020, a source confirmed to Life & Style that Sofia and Scott decided to “take some time apart” following his brief stint in a Colorado rehab facility. Days later, on May 27, the couple called it quits for good … well, sort of.

“Scott and Sofia are giving love another shot. They’re keeping it on the down-low and are still figuring things out before making it official,” a separate source exclusively told Life & Style less than two months after their breakup.

“Scott is working on himself so they don’t want to jump into a full-blown relationship or anything like that,” the insider added. “They’re taking baby steps, and are spending time together and seeing where it goes.”

Scott and Sofia first sparked reconciliation rumors after being spotted together on the 4th of July. “They missed being around each other,” the source explained. “It’s one of those ‘absence makes the heart grow fonder’ situations.” Fast forward to fall 2020, and it looks like the two are permanently on the outs. Scott and Sofia broke up again in mid-August. 

Of course, in between all the Sofia drama, it briefly appeared as though the Flip It Like Disick producer and Kourtney were giving their relationship another chance. The former flames, who share three children — Mason, Penelope and Reign — spent a lot of time together and even shared a few flirty exchanges on Instagram

However, things seemingly stayed platonic between them. “There’s a lot of water under the bridge, and while Kourtney loves having Scott around the kids more, she’s not about dating him again,” In Touch previously reported. “That’s not something she’s ready to embrace.”

To see a complete breakdown of Scott Disick’s dating history, scroll through the gallery below.