Kardashian family followers have spent years trying to decipher Scott Disick, his connection to the family, and his antics. Critics argue that Disick is manipulative and mean-spirited, while his fans insist he truly loves the Kardashians, including his ex, Kourtney. While Disick has had plenty of problems over the years, he is starting 2025 with a dose of self-awareness. In a January interview for Khloe Kardashian’s Khloe in Wonder Land, Disick opened up about his love life, insisting he needs to date women closer to him in age. Considering his sudden change of heart, we decided to look back at his relationship with the biggest age gap.

Scott Disick says he needs to date older women

Scott Disick joined Khloe Kardashian on Khloe in Wonder Land last month to discuss his love life. The father of three appears more self-aware than ever before, especially when it comes to romance. He insisted that when it’s time to plunge back into the world of relationships, he’ll probably set his sights on a woman who is a bit older than the girls he has dated in the past.

The father of three is also planning to change the way he incorporates his children into that part of his life, too. He told Khloe that while the kids would like him to have a partner, he isn’t interested in introducing them to another woman who won’t be around for the long haul. He said he only wanted to introduce them to the “right one” this time.

Disick shares three children with Kourtney Kardashian. Their eldest child, Mason, is 15. Penelope, Disick’s only daughter, is 12. Their youngest son, Reign, was born in 2014. Kardashian also has a child with her husband, Travis Barker. Disick doesn’t have additional kids.  

Scott Disick and Amelia Hamlin’s age gap relationship concerned fans

Could Scott Disick’s most recent sizeable age-gap relationship have made him a bit more cautious? It seems like it. While Scott Disick has had a string of much younger girlfriends, the age gap of his last serious relationship garnered more than a few side eyes. Disick was first spotted with Amelia Hamlin, the daughter of Lisa Rinna and Harry Hamlin, in 2020. The duo’s relationship was confirmed almost immediately. At the time, Hamlin was 19, and Disick was 38. The pair had an 18-year-age hap that left fans and followers creeped out.

The relationship ended after 11 months. While Disick hasn’t spoken out about Hamlin, there have been clues that the couple didn’t end things on a friendly note. The relationship appeared to come to an abrupt end right around the time Disck’s texts criticizing Kourtney Kardashian’s relationship with Travis Barker were leaked. According to several sources, Hamlin took issue with Disick’s continued interest in Kardashian.

The relationship probably wasn’t built to last regardless. Lisa Rinna, Hamlin’s mother, was deeply concerned by the romance. She voiced her opinion on The Real Housewives of Beverly Hills before the pair called it quits. She said learning about the romance was a “what the f**k” moment for her.