What Harry Styles' Exes Have Said About Him

Harry Styles is undeniably one of Hollywood's most coveted bachelors. You either want to be with him or be him. Since his teenage days as a member of the world-famous boyband One Direction, Styles' appeal has only grown, making him increasingly desirable over the years. And he's certainly lived it up, dating an impressive roster of high-profile partners, many of whom have spoken warmly about him.

But don't expect Styles to dish on his love life. He's famously private, choosing to let the rumors die down rather than set the record straight about pretty much anything regarding his partners. "I've never talked about my life away from work publicly and found that it's benefited me positively," the "Watermelon Sugar" singer told Rolling Stone. "There's always going to be a version of a narrative, and I think I just decided I wasn't going to spend the time trying to correct it or redirect it in some way." Even one of his ex-flings, Emily Ratajkowski, seems to have picked up on his low-key approach. After their cringey make-out sesh in Tokyo had everyone looking away, she told Spanish Vogue, "It's very bizarre to have certain experiences and then have the whole world know about them and comment on them."

But then there are others, like his former flame Emily Atack, who have shared a bit more, with Atack admitting to Reveal Magazine: "We had a nice little fling. We were never boyfriend and girlfriend. I think that's the first time I've ever admitted to what it was, because I've always just shrugged it off before" (via Cosmopolitan U.K.). But what's the general consensus from Styles' exes? Well, he seems like an all-around good guy with no real red flag to speak of — just the way he seems to like it.

Harry Styles has had his fair share of high-profile romances, but none stirred up quite as much controversy as his relationship with Caroline Flack. The late "Love Island" host was 32 when she dated a then-17-year-old Styles, resulting in more than a few raised eyebrows over the 15-year age gap. Flack, however, brushed off the criticism, insisting that age was just a number. "I already knew that he had a crush on me, he's made it pretty obvious as he's said it in magazines and said it to friends," she wrote in her "Storm In a C Cup" memoir (via Cosmopolitan). "I've never felt I was much older than Harry... We were both single, we got on well and we had a laugh."

The relationship didn't last more than a few months, and when they broke up, Styles defended her on X, formerly Twitter, saying that Flack was "one of the kindest, sweetest people I know." Meanwhile, Flack opened up about the pressure of dating a teen heartthrob under the unforgiving gaze of his fans. In her book, she confessed about how the media attention left her feeling insecure. "It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season," she penned. "Until this point I'd been comfortable in my own skin ... Then I actually started questioning who I really was. Am I fat? Am I old? Am I ugly?" But ultimately, Flack had no regrets, telling The Telegraph, "I'm not going to ever apologise for it because there was nothing at the time that was serious or bad and nobody was getting hurt."

Kendall Jenner and Harry Styles were a rare pair — despite their reportedly years-long on-and-off relationship, they've managed to keep almost everything under wraps. Still, there were hints, like their playful exchange on "The Late Late Show with James Corden" in 2019. In one round of the infamous game, "Spill Your Guts or Fill Your Guts," the model slyly asked her supposed ex, "Which songs on your last album were about me?" leaving Styles to dodge the question and stomach cod sperm instead.

But while Styles hasn't exactly dropped names, he did once hint that Jenner inspired a fair bit of his music, particularly the songs he released early on in his solo career. "She's a huge part of the album," he dished to Rolling Stone. "Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap ... And hope they know it's just for them."

And if we're looking for a bit of clarity? Khloe Kardashian has been the only one bold enough to weigh in. When asked in 2016 if they were dating, Kardashian told ET, "Do I think they're dating? Yes," she said in 2016. "I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title. But I mean, they were in St. Barts together hanging out, so to me that's dating." And there you have it — sort of. With Jenner and Styles, we may never get the full story, but a little mystery appears to be exactly how they want it to be.

Before Olivia Wilde and Harry Styles were romantically linked, they were just colleagues on the set of "Don't Worry Darling," where Wilde, as the director, was clearly Styles' biggest fan. But Wilde's enthusiasm for Styles went beyond a typical director's praise. She took to Instagram to post what might as well have been a love letter, gushing about his performance in her film. "It is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight. Enter: @harrystyles, our 'Jack' Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our 'Alice,' but he infused every scene with a nuanced sense of humanity," she penned, along with a photo of Styles looking dapper on set. "He didn't have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards."

Though their love story didn't go the distance — reportedly due to Styles' jet-setting pop star lifestyle — Wilde was candid about how much she adored him, ignoring all the noise from critics who couldn't overlook their age difference. In her interview with Vogue, she brushed off the scrutiny, noting that she was head over heels in love. "I think what you realize is that when you're really happy, it doesn't matter what strangers think about you. All that matters to you is what's real, and what you love, and who you love," she explained. "I'm happier than I've ever been. And I'm healthier than I've ever been, and it's just wonderful to feel that."

Georgia Fowler might not be Harry Styles' most famous ex, but for fans in the know, their brief fling is still iconic. Fowler was the only one of his exes to give everyone a rare POV of what he would be like as a boyfriend, thanks to a Snapchat of him casually playing Scrabble with her — at a spa, no less! And while their fling wasn't exactly a grand love affair, fans are still convinced that "Kiwi," one of Styles' hits, was inspired by the New Zealand model. Fowler, however, isn't buying it. "Ah, don't really know anything about it ... 'Definitely don't have a baby ... that's what the song is all about," she said on The Morning Show (via the Daily Mail). Plus, she also doesn't seem to want to make their past a bigger deal than fans make it out to be. "You just go and live your life, you know. Everyone is just normal people. [The tabloid attention] is really no different and I'm not going to change anything or do anything different," she once told Grazia. "So yeah."

As for Styles, he's kept the mystery alive, never confirming who "Kiwi" was actually about. And he seems to be enjoying the speculation. "I love that with writing, you get to wrap it up with a song," he told USA Today. "I understand that people will dissect stuff like that, which is amazing, that people care enough about you to try and figure out what it means."

Taylor Swift and Harry Styles might not have had the longest romance, but they were definitely the most talked-about. As two of the biggest names in pop, their relationship was under the microscope, yet we got only glimpses — until Swift dropped her award-winning album "1989." That's when fans got their real insight, as Swifties began sleuthing out which tracks were about Styles, with "Style" (of course!) and "Out of the Woods" topping the list. And they weren't reaching, either. Lines like "long hair, slicked back, white t-shirt" seemed like a dead giveaway, while the line in "Out of the Woods" about "hitting the brakes too soon" and ending up in a "hospital room" with "twenty stitches" lined up perfectly with Styles' infamous 2012 snowmobile mishap (he was later seen having a bandage on his chin).

Of course, Swift has never outright confirmed it, but she's dropped a few hints. In an appearance on "The Morning Show," she described "Style" as being about a lover you're never quite over. "'Style' is actually about those relationships that are never really done," she shared. "You always kind of have that one person who you feel like might interrupt your wedding and be like, 'Don't do it, we're not over yet.' I think everybody has that one person who kind of floats in and out of their life and the narrative is never truly over." So, is Haylor really "out of the woods"? Only time — and maybe another album — will tell.