“In the 305 just call me good luck chuck,” Scott, 38, captioned an Instagram post shared on Wednesday, April 20. In the snap, he can be seen driving a speed boat.
The caption appeared to be a reference to the 2007 movie Good Luck Chuck starring Dane Cook. In the flick, the comedian stars as the title character, Chuck, who sleeps with women and immediately afterwards, they find their “one true love.”
Scott’s Instagram post seemingly referencing the movie came hours after his ex Sofia, 23, announced her engagement to Elliot Grainge, whom she’s been with since early 2021. “Forever isn’t long enough Elliot,” she captioned a series of photos from the romantic proposal.
Sofia — daughter of Lionel Richie and sister to Nicole Richie — and Scott dated for more than three years and called it quits in August 2020 after initially breaking up in May of that same year. After their split, she was romantically linked to Elliot in January 2021. They showcased their love via Instagram in April of that year with a sweet kissing photo.
At the time, a source told Life & Style that Elliot was the “total opposite” of Scott. “She found a guy who enjoys being out of the spotlight and she’s happier than ever about that,” the insider added, noting that Sofia “really did love” the Flip It Like Disick star. However, “all the extra stuff surrounding him was a huge distraction,” the source noted.
“She’d rather spend her time studying to be an actress and doing her other projects than dodging questions about the,” they shared at the time. “When Sofia and Elliot are together — it’s just the two of them.”
Sofia isn’t the only one of Scott’s exes getting ready to walk down the aisle. He and Kourtney, 43, had an on-and-off romance from 2006 to 2015. Throughout that time, they welcomed three children, . After their breakup, the Kardashians star moved on with . Kourtney and the Blink-182 drummer, 46, went public with their romance in early 2021 and in October of that same year announced that were engaged.
A source told Life & Style following Kourtney and Travis’ engagement that it “is a bitter pill to swallow” for Scott. The insider noted that the Talentless founder “still has lingering feelings” for Kourtney, noting “she is the mother of his children so it’s only natural.”
Despite how he feels about his exes, Scott has since been linked to Rebecca Donaldson. Scott is “trying to find a woman he can settle down with” a separate source told Life & Style in December 2021. The insider added, “His friends say he’s not happy playing the field anymore.”