When it comes to his famous son, Desmond Styles is undeniably a Styler. As Harry Styles’ biggest supporter and champion, Desmond keeps a close eye on his son’s life—even in matters of the heart. Despite Harry being all grown up, there was one ex-girlfriend who did not receive Desmond’s approval.
Harry Styles, known for his eclectic love life, has never let age dictate his romantic choices. Over the years, the British singer has been linked with several older women. For instance, his relationship with Olivia Wilde, which had a ten-year age gap, lasted nearly two years before ending. Similarly, Harry’s past relationships with Emily Ratajkowski, Tess Ward, Taylor Swift, Kimberly Stewart, and Camille Rowe featured significant age differences. Notably, he also dated the married DJ Lucy Horobin, who was 14 years his senior—a relationship that stirred quite a bit of controversy.
Despite public and media scrutiny, Harry seemed unfazed by age differences. “How old is old?” he once replied when questioned about his preference for older women, adding that he didn’t consider any woman older than his mother, Anne, to be problematic.
However, there was one relationship that particularly drew Desmond Styles’ concern. When Harry was just 17, he dated the late TV presenter Caroline Flack, who was 32 at the time. This 15-year age gap caused quite a stir, especially given Harry’s young age. Desmond voiced his disapproval in an interview with the Daily Record, acknowledging the relationship as “a bit extreme.”
Harry and Flack’s relationship began in 2011, shortly after One Direction won “The X-Factor,” with Flack hosting its sister show, “The Xtra Factor.” Their brief romance ended amid media frenzy and public backlash. Harry was quick to clarify that the split was mutual, tweeting, “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 this, Flack faced harsh criticism, with some accusing her of grooming the teenager.
The scrutiny took a toll on Flack. In her memoir, “Storm in a C Cup,” she described the harsh public reaction and the personal attacks she faced. “In the street, people started shouting at me ‘pedophile’ and ‘pervert,’” she recounted, reflecting on the impact of the public’s response.
Things worsened for Flack in 2019 when she faced legal issues following an alleged domestic incident. Despite her ongoing struggles with mental health, the situation continued to escalate. Tragically, Flack took her own life in November 2020. Harry Styles honored his ex by wearing a black ribbon at the Brit Awards, a poignant tribute to their past and her enduring impact.
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