When it comes to his famous son, Desmond Styles is definitely a Styler. He’s his son’s biggest supporter and champion. Even though Harry Styles is all grown up now, Desmond still likes to keep an eye on him, especially regarding his love life — and there was one now ex-girlfriend that Desmond definitely didn’t approve of.
As the timeline of Harry’s relationships proves, age is just a number for the Brit when it comes to his choice of love interests. People reports that Harry has locked lips and enjoyed relationships with several older women over the years. Olivia Styles’ relationship with Harry is a recent example. There was a ten-year age gap between the singer and the mom-of-two, who dated for nearly two years before finally going their separate ways. Harry’s also been linked to Emily Ratajkowski, Tess Ward, Taylor Swift, Kimberly Stewart, and Camille Rowe, who all beat him in the age stakes. And per the Daily Mail, Harry dated the married DJ Lucy Horobin, who’s 14 years older than him. That relationship was a hotbed of controversy for those bothered about such things.
However, Harry couldn’t have cared less. “How old is old?” You magazine asked an 18-year-old Harry. “Any woman older than my mom, Anne—who is 43,” he answered. Still, there was one older woman that Prince Harry, Duke of Sussex, and Harry, Commoner of Styles, were once linked to — and Harry Styles’ dad didn’t approve of that particular ex-girlfriend at all.
When Harry was 17, he dated the late TV presenter Caroline Flack, who was 32 then, making for a 15-year age gap — a pretty big stretch when one of the partners isn’t even old enough to legally buy a pint of beer. Although, plus side, you do get a designated driver. “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,” Harry’s dad Desmond Styles told Daily Record.
Harry and Flack dated for a few months in 2011 when One Direction had just won “The X-Factor” and Flack was presenting its sister show “The Xtra Factor.” After they split, speculation emerged that Harry had moved on to a newer model. Something he immediately shot down. “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,” Styles tweeted. Still, Flack faced significant backlash for dating the teen. “You’re a victim,” one commenter replied to Harrty’s tweet. “‘dump Caroline’ ???? Baby, she was grooming you,” they continued.
Flack blamed the scrutiny and the haters for their relationship ending. ”In the street, people started shouting at me ‘pedophile’ and ‘pervert,'” she wrote in “Storm in a C Cup,” her 2004 memoir. “A ‘One Direction’ fanzine had me as a voodoo doll, with arrows (pins) pointing at various parts of my anatomy.”
Tragic ending
Harry Styles and Caroline Flack managed to keep their relationship on the down low until just before they split. “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,” she explained, per Mirror. “It was only when it became public knowledge that things turned sour. At the beginning, it was all very playful. He joked about being attracted to older women.
After their split, good old-fashioned misogyny soon raised its ugly head. “It had turned from ‘Harry Styles is so young’ to ‘Caroline Flack is so old.’ I’d become a laughing stock. Mostly it would be jokes, which I could cope with, but I would get ‘Cougar!’ or ‘MILF’ shouted at me in the street,” she wrote in her memoir.
Things became even worse for Flack in 2019 after it was announced that she had allegedly assaulted her boyfriend during a domestic violence incident. The Guardian reports that prosecutors pushed for a caution to be issued. Still, the Metropolitan Police went full steam ahead and criminally charged her, despite Flack having a history of mental illness. In November 2020, she took her own life. Per People, Styles paid tribute to his ex by wearing a black ribbon to the Brit Awards in her honor.