Desmond Styles has always been one of Harry Styles’ biggest fans and staunchest supporters. As Harry evolved from a teenage pop star to a global icon, his father’s unwavering pride and attention never wavered. Even as Harry navigates his adult life, including his romantic endeavors, Desmond has occasionally weighed in, especially when it comes to partners who spark widespread public interest or controversy. There was one past girlfriend in particular that Desmond made it clear he did not approve of, and their relationship has remained a source of public fascination and heated debates.
Throughout his career, Harry Styles has frequently been linked to older women. For the former One Direction member, love seems to transcend the boundaries of age. His relationship history, as documented by outlets like *People*, demonstrates his pattern of dating women who are several years his senior. Most recently, his romance with actress and director Olivia Wilde made headlines. With a ten-year age difference between them, the couple dated for nearly two years, sparking considerable attention and some controversy. Beyond Wilde, Harry has also been romantically linked to model Emily Ratajkowski, chef and food blogger Tess Ward, pop star Taylor Swift, socialite Kimberly Stewart, and model Camille Rowe—all older than him. According to the *Daily Mail*, Harry was also briefly involved with married DJ Lucy Horobin, who was 14 years his senior. That particular relationship attracted a wave of criticism and gossip.
Harry, however, has often shrugged off societal judgments concerning age gaps in relationships. At the age of 18, when asked by *You Magazine* about his thoughts on age, he cheekily replied, “How old is old? Any woman older than my mom, Anne—who is 43.” Yet, despite Harry’s typically carefree attitude, there was one romance that stirred public sentiment and drew the disapproval of his father Desmond.
At just 17, Harry entered into a relationship with Caroline Flack, a well-known TV presenter at the time. Their 15-year age difference became a major talking point, as Harry was still a teenager. While it could have been seen as a badge of pride for some fathers, Desmond Styles had reservations. “With Caroline Flack, you can imagine, dads and sons, it’s like, ‘Fair play, son.’ But it was a bit ridiculous—32 or whatever she was and 17. It’s a bit extreme, really,” Desmond shared with the *Daily Record*.
Harry and Caroline dated briefly in 2011, right as One Direction was on the cusp of mega-stardom following their success on *The X Factor*. Caroline was then hosting its companion show, *The Xtra Factor*. Their romance, though short-lived, became public fodder, and Harry felt compelled to defend Flack in the face of growing scrutiny. He tweeted, “Please know I didn’t ‘dump’ Caroline. This was a mutual decision. She is one of the kindest, sweetest people I know. Please respect that.” Despite his appeal, the backlash persisted. Critics accused Flack of exploiting their age difference, with comments ranging from “You’re a victim” to accusations of grooming.
In her 2014 memoir, *Storm in a C Cup*, Flack spoke candidly about the intense public reaction and how it contributed to their breakup. “In the street, people started shouting at me ‘pedophile’ and ‘pervert,'” she revealed. Flack described how she was portrayed as a villain, even appearing as a voodoo doll in One Direction fan magazines. The relentless harassment took its toll on her, and she ultimately blamed the public pressure for their split.
The couple tried to keep their romance private, but the public’s curiosity and scrutiny made it impossible. Flack recounted, “I’ve never felt I was much older than Harry. I still feel 18, and I probably act that way half the time. Although it was just a bit of fun, we decided it was best to keep it to ourselves as we were both working for Simon Cowell.” However, once their relationship became known, it soured. Misogynistic tropes quickly emerged, with Flack becoming a target. “It had turned from ‘Harry Styles is so young’ to ‘Caroline Flack is so old.’ I’d become a laughing stock,” she wrote, noting that taunts of “Cougar” and “MILF” followed her everywhere.
Flack faced even darker days in 2019 when she was accused of assaulting her boyfriend. Despite her struggles with mental health, the Metropolitan Police pressed criminal charges. Tragically, Flack died by suicide in February 2020. In a subtle but poignant tribute, Harry Styles honored her memory by wearing a black ribbon at the Brit Awards, acknowledging a chapter of his life marked by both fondness and pain.
This chapter in Harry’s life is a reminder of how media and public scrutiny can shape narratives and deeply affect personal lives. It serves as a reflection on fame, relationships, and the weight of public opinion in the lives of those in the spotlight.