Scott Disick’s Dating Future: Penelope’s Demand for ‘Older’ Women and Khloé’s Matchmaking Mission on The Kardashians
The latest season of Hulu’s hit reality series, The Kardashians, continues to deliver intriguing family dynamics and personal revelations. In a particularly candid moment from the October 19 episode, Scott Disick’s own daughter, 11-year-old Penelope Disick, stepped into the role of an unexpected matchmaker, offering her father some direct and rather specific advice on his love life. The conversation, which quickly went viral, centered on Penelope’s firm belief that Scott, 40, should seek out a partner who is “older” than his previous girlfriends, sparking a broader discussion within the family about Scott’s romantic future.
The discussion unfolded during a heart-to-heart session involving Scott, his former partner Kourtney Kardashian’s sister Khloé Kardashian, and matriarch Kris Jenner. Khloé, 39, who has long been a supportive figure in Scott’s life, initiated the conversation by asking her niece, Penelope, what “qualities” she thought were essential in a potential girlfriend for her dad. Without hesitation, Penelope delivered a response that immediately captured the attention of both her family and the audience: “Older.”
Penelope Disick’s Unfiltered Wisdom: Why Age Matters
Penelope’s immediate and unequivocal answer regarding age wasn’t just a throwaway comment; it came with a clear conviction that suggested a deep understanding of her father’s dating patterns. Khloé, surprised yet amused by the directness of her niece, then prodded further, asking, “Older than what Scott is used to?” This opened the door for Khloé to reveal that Scott had often expressed an interest in dating women in their late 20s. However, Khloé herself felt that focusing on women in their 30s would be a more suitable direction for him.
The moment Penelope heard this, she turned to her father with a look of genuine concern and a touch of reprimand. “You’re 40,” she reminded him pointedly, emphasizing the significant age gap between Scott and the young women he previously dated. Her directness didn’t stop there. Penelope continued, “You’re not going to date someone 19.” Scott, seemingly caught off guard but also acknowledging the truth in his daughter’s words, responded with a sheepish, “I would, but it’s not a good look.” This exchange highlighted the maturity of Penelope’s perspective and the undeniable impact of such age differences, especially when viewed through the lens of family and public perception.
This candid conversation quickly resonated with viewers, many of whom have long observed Scott’s dating history. For an 11-year-old to articulate such a mature understanding of appropriate relationship dynamics speaks volumes about the open communication within the Kardashian-Jenner household. Penelope’s insistence on an “older” partner isn’t merely about numerical age; it suggests a desire for stability, shared life experiences, and a level of maturity that she believes would better complement her father’s stage of life.
@pandkourt Excuse me, Bruh
♬ Excuse me BRUHH – Castro🇭🇹
Beyond Age: Penelope’s Ideal Partner Qualities for Scott
Penelope’s insightful advice wasn’t limited to just age. She went on to outline a comprehensive list of qualities she believes her father should look for in a potential girlfriend, further showcasing her thoughtfulness and desire for her dad’s happiness. “Good personality. She can be pretty… Someone who goes to the gym because you need to go to the gym also,” Penelope declared. This list moved beyond superficial traits, emphasizing compatibility and even subtly hinting at Scott’s own well-being.
The suggestion about a partner who “goes to the gym” was particularly poignant. Scott has recently been recovering from injuries sustained in a car accident, which left him with back problems and prompted a period of weight gain. Penelope’s comment, while seemingly simple, reflects a child’s inherent concern for their parent’s health and vitality. It implies a desire for a partner who not only shares a healthy lifestyle but also motivates Scott to prioritize his physical well-being. A “good personality” speaks to the need for emotional connection and genuine companionship, while “pretty” is a common, understandable desire from a child who wants their parent to be with someone they find attractive.
Later in the episode, Penelope reiterated her earnest desire for her father to find love again to both Khloé and Kris. “I want him to have a girlfriend,” she admitted, underscoring the sincerity of her advice and her hopes for Scott’s future. This sentiment highlights a universal desire among children to see their parents happy and settled, especially after a significant separation or period of singlehood. Penelope’s proactive approach signals a shift in the family dynamic, where the younger generation is now playing an active role in guiding their elders.
The Matchmaking Mission: Khloé and Kris Weigh In
Khloé Kardashian has consistently been a pillar of support for Scott, often acting as a confidante and a bridge between him and the rest of the family. Her engagement in this matchmaking discussion with Penelope indicates a genuine desire to see Scott find happiness. Khloé’s suggestion of women in their 30s as opposed to late 20s aligns perfectly with Penelope’s “older” directive, creating a united front in their quest to find Scott a suitable partner. Kris Jenner, ever the supportive matriarch, also lent her ear to the conversation, showing the family’s collective concern for Scott’s romantic life.
Scott, for his part, explained to Khloé and Kris that he is currently single and primarily focusing on his children. This dedication to his kids, Mason, Penelope, and Reign, has been a consistent theme in his post-Kourtney life. Additionally, Scott has been navigating his recovery from the car accident, with Khloé having reportedly been instrumental in helping him get back to his “normal self.” This period of self-focus and recovery naturally puts a pause on active dating, but the family’s encouragement suggests they believe he’s ready, or soon will be, to explore new romantic connections.
Scott’s Dating History: A Pattern Penelope Acknowledges
To understand the full weight of Penelope’s advice, it’s essential to look at Scott Disick’s romantic history. Scott and Kourtney Kardashian, 44, shared a turbulent, on-again-off-again relationship for nearly a decade, during which they had their three children. Their final split occurred in 2015. Following their separation, Scott embarked on a series of high-profile relationships, many of which garnered significant media attention due to the considerable age gaps involved.
His most notable post-Kourtney relationships included model Sofia Richie, whom he dated from 2017 to 2020. At the time they began dating, Scott was 34 and Sofia was 19, making for a 15-year age difference. Following their split, Scott dated model Amelia Hamlin from late 2020 to late 2021. Amelia was just 19 when they started seeing each other, while Scott was 37, marking an 18-year age gap. More recently, he had a brief relationship with model Rebecca Donaldson in 2022. While the exact age difference was less pronounced than with his previous partners, she was still in her mid-20s, making her significantly younger than Scott.
These past relationships, characterized by Scott dating women significantly younger than himself, are undoubtedly what Penelope was subtly, yet firmly, addressing. From a child’s perspective, witnessing a parent repeatedly date partners who are closer in age to their older siblings or even themselves might lead to questions about compatibility and long-term stability. Penelope’s “older” recommendation can be seen as a direct response to this observed pattern, a plea for her father to find a partner who is more aligned with his current life stage, offering a sense of consistency and mature companionship.
The “Crush” on Khloé: Playful Banter or Something More?
Amidst the serious discussions about Scott’s dating life, a lighter, yet equally intriguing, moment occurred when Kris Jenner, 67, offered her own theory. “I think Scott probably has a crush on Khloé,” she playfully suggested during the episode. This statement immediately sparked a reaction, and Scott’s response only added to the amusement and speculation.
Scott didn’t deny it; instead, he enthusiastically gushed over Khloé in front of Kris. “She’s funny, she’s kind, she’s sweet, she’s cute, she’s got all the characteristics I want. That’s what I’m saying,” Scott affirmed, listing a myriad of admirable qualities. This playful banter underscored the incredibly close, almost sibling-like bond that Scott and Khloé have shared for years. Their relationship has always been marked by deep affection, loyalty, and a unique understanding, often seen as the most solid friendship within the extended family.
While the “crush” comment was likely made in jest, reflecting the warmth and familiarity between them, it highlights the kind of partnership Scott truly values: one built on genuine affection, humor, and shared history. Khloé embodies many of the “good personality” traits Penelope also outlined, further emphasizing that Scott’s ideal partner might be someone who mirrors the positive dynamics he already shares with his chosen family members. This segment, while humorous, provided a glimpse into the emotional landscape Scott is navigating as he contemplates finding love again.
The Broader Context of Dating in the Kardashian Spotlight
Dating as a public figure, particularly within the orbit of the Kardashian-Jenner family, comes with a unique set of challenges. Every relationship is scrutinized, every interaction analyzed, and every breakup becomes headline news. For Scott Disick, who has essentially grown up on reality television, this scrutiny is amplified. His past relationships have been dissected by both the media and the public, creating an immense pressure to make the “right” choice when it comes to a partner.
Furthermore, the evolving dynamics within the family undoubtedly influence Scott’s approach to dating. With Kourtney happily married to Travis Barker and building a life with him, Scott might feel an increased desire to find his own lasting happiness. Seeing his children’s mother in a stable, loving marriage could inspire him to seek a similar foundation for himself, moving away from more transient relationships. Penelope’s advice, therefore, can be seen not just as a child’s innocent wish, but as a reflection of the family’s collective hope for Scott to find a partner who brings stability, maturity, and genuine companionship into his life.
The family’s intervention, led by Penelope and supported by Khloé and Kris, underscores a crucial aspect of their relationships: despite their differences and past issues, they remain a unit that genuinely cares for one another’s well-being. They want to see Scott thrive, both personally and romantically, and are willing to offer their candid thoughts and support to help him navigate the complexities of finding love in the public eye.
What Lies Ahead for Scott Disick’s Love Life?
Penelope Disick’s candid advice has undoubtedly thrown a new variable into Scott Disick’s dating equation. Her clear preference for an “older” woman, coupled with Khloé’s matchmaking efforts and Kris’s observations, paints a picture of a family united in their desire for Scott to find a mature, stable, and genuinely compatible partner. While Scott’s immediate focus remains on his children and his recovery, the seeds of a new romantic chapter appear to have been sown, guided by the surprising wisdom of his 11-year-old daughter.
Whether Scott will heed Penelope’s advice and seek out an “older” woman remains to be seen, but the conversation has certainly put the idea front and center. His openness to the discussion and his acknowledgment of his past choices suggest a willingness to consider a different path. As new episodes of The Kardashians season 4 continue to premiere Thursdays on Hulu, viewers will undoubtedly be watching closely to see if Scott Disick’s dating future takes a turn towards maturity, guided by the sage advice of his beloved daughter, Penelope.