The One Woman Both Prince Harry And Harry Styles Were Once Linked To

The following article contains mentions of suicide.

Unsurprisingly, being a member of the royal family comes with a certain amount of scrutiny. For example, the media loved to comment on Prince William's relationship with Kate Middleton, even dubbing the latter "Waitey Katey" because she waited for nearly a decade to get married. Before tying the knot with Meghan Markle, Prince Harry's relationships were also tabloid fodder. Notably, he dated Chelsy Davy off and on for several years, and she was even Harry's +1 to William and Kate's wedding, per Marie Claire. Still the pressure of such a high-profile romance took a toll on Davy, who told The Times that "[the media attention] was so full-on: crazy and scary and uncomfortable."

Another Brit whose relationships have long been clickbait is Harry Styles. He may not be royal, but being a one-time boy bander has its perks. Since quitting One Direction and launching his solo career, Styles' love life has also taken center stage. While working on the set of "Don't Worry Darling" in 2021, the "Watermelon Sugar" singer got together with actor-director Olivia Wilde. They've since split, and fans are already speculating about Styles' romantic future. Before Wilde, Page Six reports that Styles was linked to other A-listers, including Taylor Swift, Nicole Scherzinger, and Kendall Jenner.

Beyond sharing a British heritage, a first name, and a publicized love life, Prince Harry and Styles have even more overlap. Once, they reportedly dated the same woman. (No, not at the same time!)

When Harry Styles began dating Olivia Wilde, the media was quick to point out their 10-year age gap, but it wasn't the first time Styles had dated a much older woman. According to Glamour UK, the pop star met TV presenter Caroline Flack on "The X Factor" in 2011 when he was 17 and she was 31. "I already knew that he had a crush on me, he'd made it pretty obvious," Flack wrote in her autobiography, "Storm in a C Cup" (via Seventeen). "He'd said it in magazines and he'd said it to friends." The two then struck up a relationship, which wasn't well received by One Direction fans. Writing that things began to go south when Styles was spotted leaving her house one morning, Flack added, "It was open season ... In the street, people started shouting at me 'pedophile' and 'pervert.'" It was this negative attention that ultimately prompted the couple to break things off.

But, before Styles, Flack was also dogged by the paps for her tryst with Prince Harry, as the Duke of Sussex detailed in his memoir, "Spare" (via Hello!). As soon as photos of the two hit the Internet, "Within hours a mob was camped outside Flack's parents' house, and all her friends' houses, and her grandparents' house," Harry explained. In the end, as much as they might have liked each other, the media attention became too much to handle.

In 2020, Page Six reported that Caroline Flack died by suicide while she was in the middle of a trial for alleged assault of her then-boyfriend. When they heard the news, both Prince Harry and Harry Styles grieved for Flack. According to Harper's Bazaar, Styles showed up to the 2020 Brit Awards wearing a black ribbon. Though the singer didn't comment on the ribbon, the color "symbolize[s] remembrance or mourning," as the outlet noted. Furthermore, the timing lines up, as Styles' mother had recently taken to Twitter to pay tribute to her son's ex. "Heartbreaking #ripcarolineflack," she wrote, alongside a broken heart emoji.

Prince Harry didn't say anything publicly, but the sad news made him reflective of the short time he had shared with Flack. "I felt so awful for her family," he wrote in his memoir, "Spare" (via Hello!). "I remembered how they'd all suffered for her mortal sin of going out with me." It had been well over a decade since their first meeting, but the Duke of Sussex still remembered his initial impression of Flack. "She'd been so light and funny that night we met. The definition of carefree," he recalled.

However, Flack's agent, Alex Mullen, did not take kindly to the prince's recollections of his client. "[Harry] writes as if he has any idea why Carrie took her own life, parroting media reports as if they're reality. Blaming the press because that's what he read about it. He knows nothing," Mullen said, per Sky News.

If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.