Scott Disick attends ASOS celebrates partnership with Life Is Beautiful at No Name on April 25, 2019 in Los Angeles, California. (Photo by Presley Ann/Getty Images)
Penelope Disick is keeping it real with her serial bachelor dad, Scott Disick. On this week’s episode of The Kardashians, Scott and Kourtney Kardashian’s 11-year-old daughter made a cameo while her grandma, Kris Jenner, and her aunt, Khloe Kardashian, discuss working with a matchmaker to set Scott up on a date.
Penelope’s number one requirement for her dad is to make sure he dates someone “older” this time around. Scott, 40, has a history of dating significantly younger women, like models Sofia Richie and Amelia Hamlin, who are now 25 and 22, respectively. When Khloe says that Scott is interested in women in their 20s, Penelope replies, “No, 20s? You’re 40! You’re not going to date someone 19.”
Scott admits, “I would, but it’s not a good look.” He previously said in the show’s first season that he’s looking for someone in their “upper 20s.” He added in a confessional, “But not over 30. Oh f—, whatever, if I love somebody, it doesn’t matter their age.” As for Penelope’s other requirements, she lists: “Good personality, she can be pretty, someone who goes to the gym because you need to go to the gym.” Scott’s daughter supports her family’s matchmaking plans, adding, “I want him to have a girlfriend.”
Scott’s Love Life
Kris and Khloe set him up on a date with lingerie business owner Celine Nehoray. She and Scott go on a date, but it doesn’t seem like there is a connection. Later, Scott tells Khloe he enjoyed himself. He notes that he probably talked to her more than the girls he’s dated for years but worries that she hasn’t been in long-term relationships or experienced any hardships.
Elsewhere in the episode, Kris says in her confessional interview that Scott “probably has a crush on Khloe.” The matriarch adds that she doesn’t hold it against him, adding, “Listen, I have a crush on Khloe; everyone has a crush on Khloe!” Scott insists that he’d “obviously” never look at Khloe sexually, even though he enjoys teasing her about a potential romance. However, Scott notes that he wants someone who will “stick around,” just like Khloe has with her exes.
Scott and Kourtney share three children together. Besides Penelope, they have sons Mason, 13, and Reign, 8. After a lengthy, on-again-off-again romance, the former couple split in 2015 for good. Kourtney has since moved on with her husband, Travis Barker, whom she is having their first child together with soon.
Season 4 of The Kardashians is currently streaming on Hulu, with new episodes out on Thursdays.
The Most Unexpected Celebrity Match-Ups
Hollywood tends to date within the same pool. Though some couples have got their start from working together on the same set, others have met each other at events. Age is not a factor for celebrities looking for love, as many have dated people over ten years older or younger than them. Some couples are still together, but for the really bizarre ones, their romances fizzled out before we could come up with a cute ship name (like the iconic Bennifer). The love life of the rich, famous, and good-looking spark interest in online discourse. Rumors of cheating and breakups hit social media on a daily basis, but unless the celebrities themselves clear the air, it is all hearsay.
Most celebrity divorces have filed documents citing “irreconcilable differences,” which is a term used as a catch-all when the parties involved want to keep the specific reasons under wraps. For example, in Britney Spears and Sam Asghari’s divorce, they cited irreconcilable differences despite rumors of Britney cheating on her husband with “at least one” male staff member.
Some of our favorite couples are the ones who have withstood the test of time, while some of the biggest breakup news of the year was of couples we thought were going the distance. Sophia Vergara and Joe Manganiello and Taylor Swift and Joe Alwyn were just two couples who were together what fans thought were “couple goals. A-listers tend to keep their relationships under wraps, but there is no shortage of dating shows to feed our needs for front-row drama.
As we’ve seen with stars whose every move is watched, their relationships have been judged every step of the way, like Kanye West and his new wife, Bianca Censori. Other couples have no photos posted together on their social media apps, so as to not further fuel media coverage. That doesn’t stop the paparazzi or fans from snapping pics any chance they get, though.
Take a look below to see which celebrities we think are the most random match-ups.
Kim Kardashian and Pete Davidson
The pair met on the set of Saturday Night Live in 2021 when Kim was the host. Kim dated Pete for nine months, following her split from Kanye West, making this match up pretty shocking. Pete has dated many famous people over the years, so it has become a running joke on social media to nominate Davidson to date the next single Hollywood star. He even got a few tattoos and even branded Kim’s name on him!
These two are a match-up that threw us all in for a loop. The punk rock princess and the rapper dated for three months at the beginning of 2023. It’s unclear how they met, but they took their romance across the pond for Paris Fashion Week. In July, ET reported that the two were seeing each other again casually.
Megan Fox and Machine Gun Kelly
The actress, who is four years older than the rapper-turned-rocker, has plans to marry MGK. The pair first met on the set of the thriller Midnight in the Switchgrass in March 2020. Fox later appeared as Kelly’s love interest in his music video for “Bloody Valentine.” By July, the couple had confirmed their relationship when they gave their first joint interview, where Fox called Kelly her “twin flame.” There were rumors of a split between the couple amidst cheating allegations, but it seems as though the couple got through it and are working on their relationship.
Who would’ve thought that the punk rock drummer and a Kardashian would tie the knot — three times?! Kourtney and Travis have been neighbors and friends for years, and now they are expecting their first child together — a son — after undergoing IVF treatments.
Harry Styles and Olivia Wilde
Olivia Wilde and Harry Styles are "taking a break" from their relationship after nearly two years together, People Magazine reports.
Their relationship was seemed to start during the pandemic, making Harry and Olivia’s pairing that much more juicy. Olivia was split from Jason Sudeikis, whom she shares two young children with. Harry is ten years her junior, and the two met on the set of Wilde’s Don’t Worry Darling. Though the couple called it quits in November 2022, Harry has a huge Olivia tattoo on his upper thigh.
Chelsea Handler and 50 Cent
Special shout out to my favorite ex @50cent (and the only ex-boyfriend I am still asked about in every interview) who gets an extra special shout out in my @hbomax special. Now, everyone will know that you’re one big fat teddybear. Xx pic.twitter.com/j20l7XUhgE
The comedian called 50 one of her favorite exes back in 2020. Though they only dated for two months in 2010, Handler told ET Canada he was “a sweetheart” and “fun to be around. My friends loved hanging out with him. I loved hanging out with him. It was a pretty short-lived romance.” The rapper opened up about the relationship in his 2020 book Hustle Harder, Harder Smarter, revealing he met Handler while appearing on her show and immediately began pursuing her. He admitted they were an odd couple,” but it was Handler’s ambition and independence that caught his attention.
Grimes and Elon Musk
The Tesla, SpaceX, and X CEO and musician Grimes made headlines when they stepped out at the 2018 Met Gala together. Since then, they’ve been on-and-off relationship, during which they’ve welcomed two children. In early 2022, Grimes told Vanity Fair, “I would probably refer to him as my boyfriend, but we’re very fluid. We live in separate houses. We’re best friends. We see each other all the time.”
Channing Tatum and Zoe Kravitz
Zoë Kravitz holding on to Taylor Swift, and Channing Tatum with his beer at Jack Antonoff and Margaret Qualley's wedding 💍 pic.twitter.com/vzijHjU9X6
Two years after the two were spotted in New York together, and they still seem to be going strong, attending a wedding recently with other celebrities. Though the couple has been photographed together by paparazzi, neither Channing nor Zoe have posted any pictures of themselves publicly. As we previously reported, they like to keep their relationship low-key. The couple connected two years ago when Kravitz cast Tatum to star in her directorial debut Pussy Island. She is five years younger than the Magic Mike hunk.
Laila Abuelhawa is the Top 40 and Hip-Hop pop culture writer for Beasley Media Group. Being with the company for over three years, Laila's fierce and fabulous red-carpet rankings have earned her a feature on 'The Late Show with Stephen Colbert!' Her favorite stories are those surrounding the latest in celebrity fashion, television and film rankings, and how the world reacts to major celebrity news. With a background in journalism, Laila's stories ensure accuracy and offer background information on stars that you wouldn't have otherwise known. She prides herself in covering stories that inform the public about what is currently happening and what is to come in the ever-changing, ever-evolving media landscape.
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