Scott Disick's Most Scandalous Age Gap Relationships

Scott Disick's dating life is nothing short of controversial, thanks to his seemingly particular taste in women. The "Keeping Up With The Kardashians" star is notorious for dating younger partners following his split from Kourtney Kardashian. Disick's dating preference apparently doesn't sit well with his daughter, Penelope Disick. In a 2023 episode of "The Kardashians," she blasted her father's choice of girlfriends. "[She should be] older. 20s? You're 40! You're not going to date someone 19," Penelope savagely told Disick (via Entertainment Tonight). "A good personality. She can be pretty. Someone who goes to the gym because you need to go to the gym."

Although Disick has been with several younger girls, his love for Kardashian remains. In November 2020, a source told Us Weekly that he is open to getting back together with the reality star. "Scott has always loved Kourtney, and the door is open on his side in case she ever wants to take their relationship back to a romantic place," the insider claimed.

That may not happen, though, as Kardashian is happily married to Travis Barker. With Kardashian fully moved on, it's no surprise that Disick is doing the same. But in his defense, he wasn't really looking for young girls. "They happen to be attracted to me because I look young," he told Andy Cohen on "Keeping Up With the Kardashians" reunion (via Page Six). "That's what I'm telling myself." Here's a look at some of his controversial exes with significant double-digit age gaps.

Scott Disick and Christine Burke reportedly had a fling in 2016. At the time, he was 32, and she was 20. Despite the age gap, the pair instantly clicked. "It's very new, but Scott and Christine are dating," a source confirmed to Entertainment Tonight. "The family has known about her before these pictures came out." That same year, the two were seen kissing on board a yacht in France, seemingly confirming their relationship. However, the romance didn't last long, and the two parted ways.

Fast forward to 2021, the ex-couple reconnected and sparked romance rumors yet again. Disick and Burke were photographed together in Hollywood along with influencer Sergio Farias on November 15. Shortly after the outing, the pair was spotted again having dinner at Nobu on November 26. Disick's outing with Burke came shortly after his split from Amelia Hamlin, who reportedly pulled the plug on their relationship after almost a year of dating. 

Scott Disick seems to have a penchant for rekindling relationships with past flames. In 2020, he was spotted with his ex, Bella Banos, shortly after his failed romance with Sofia Richie. Disick was first linked to Banos, who is 13 years his junior, in 2017 after being caught together in his Costa Rica hotel room during a family vacation filmed for "Keeping Up With the Kardashians."

At the time, Banos told In Touch that she and Disick had become really close. She recalled how they started out as friends and eventually got to know each other on a different level. "Scott will call and say, 'I miss you. I want to see you,'" she added. "He always flies me to wherever he is. We spend so much time together." Banos expressed her trust in Disick, particularly regarding his complicated relationship with Kourtney Kardashian. He maintained that he was just good friends with his baby mama. 

One of Scott Disick's most talked-about romances was with Sofia Richie, who is 15 years younger than him. The two were in an on-again, off-again relationship for nearly three years before officially calling it quits in 2020. For a time, Disick and Richie's relationship seemed serious. They even got approval from Kourtney Kardashian. "Kourtney thinks Sofia brings out the best in Scott and is happy for them," a insider told Us Weekly 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."

However, in 2021, Disick revealed that Kardashian was the reason behind his split from Richie. Disick claimed Richie doesn't want to share him with his famous ex. She even issued an ultimatum, "'You have to choose me or Kourtney.'"

Disick admitted that Richie's feelings about his relationship with Kardashian aren't totally wrong. "I realize that Sofia has been an absolute trooper, but the truth is anybody dating somebody is going to feel neglected when their significant other is spending more time with their ex than with them," he said in an episode of "KUWTK." "I'm never going to give up my relationship with Kourtney and the co-parenting we have. Nothing in a million years will be worth what we have."

In 2020, Scott Disick was seen hanging out with Amelia Hamlin at a Halloween party. By November of the same year, the two appeared to go public with their romance as they walked together at the beach. However, the couple ultimately ended their romance in September 2021. A source told Us Weekly the split "wasn't related to the messages Scott sent about Kourtney" and that the breakup "was coming regardless."

Another insider said Hamlin was the one decided to end their relationship after realizing things would never work out. "Amelia's done with Scott for now. She wants to be strong and to move on," a source told E! News. "She has had enough, and it was time." The source added that Hamlin's family and friends were very supportive of her decision, reminding her that she deserves better. Disick is eighteen years older than Hamlin, which likely added more stress to their romance.

Scott Disick and Rebecca Donaldson, who have an 11-year age gap, first sparked dating rumors in April 2022 after being spotted holding hands. At the time, a source dished to Us Weekly that things were "going well" and that "he's very attracted to her." The insider added, "It's still a new relationship, and he's taking it day by day."

Disick even brought Donaldson to the premiere of "The Kardashians" and introduced her to his Kardashian-Jenner family. The source noted that "him introducing her to the family and having her at the Kardashian premiere meant a lot to him."

But their whirlwind romance didn't last long. By June 2022, Disick and Donaldson called it quits, with sources claiming they were never serious. Despite the split, there's no bad blood between them. "They've parted ways amicably," an insider told E! News. "And she's encouraged him to spend some time focusing on himself and finding what makes him happy."