Harry & Olivia Just Broke Up After Being Together For Almost 2 Years—Look Back at Who Else He’s Dated

Harry Styles, Taylor Swift, Olivia Wilde
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As the world’s most wanted man (at least, according to Rolling Stone), there’s an understandable interest in who Harry Styles is dating and his past and present relationships.

Since his debut in the industry more than a decade ago—first as a member of One Direction 2010 and then as a solo singer in 2017—Styles has made a name for himself in the music industry for love songs like “Cherry,” “Falling,” “Adore You” and “As It Was.” But while he’s been vulnerable in his music, Styles has also been private about his love life in public. “I’ve never talked about my life away from work publicly and found that it’s benefited me positively,” he told Rolling Stone in 2022. “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.”

Styles, who played his first queer character in 2022’s My Policeman, also addressed speculation around his sexuality. “Sometimes people say, ‘You’ve only publicly been with women,’ and I don’t think I’ve publicly been with anyone,” he said. “If someone takes a picture of you with someone, it doesn’t mean you’re choosing to have a public relationship or something.” He continued, “I think everyone, including myself, has your own journey with figuring out sexuality and getting more comfortable with it.” He also responded to the backlash his past and current relationships have received from some members of his fanbase. “Can you imagine going on a second date with someone and being like, ‘OK, there’s this corner of the [fanbase], and they’re going to say this, and it’s going to be really crazy, and they’re going to be really mean, and it’s not real,'” he said. “‘But anyway, what do you want to eat?'” He continued, “It’s obviously a difficult feeling to feel like being close to me means you’re at the ransom of a corner of Twitter or something. I just wanted to sing. I didn’t want to get into it if I was going to hurt people like that.”

While he’s been private about most of his relationships, there remains interest in who Harry Styles is dating. Read on for what we know about Harry Styles’ dating history and his past and present relationships.

Olivia Wilde (2021 – 2022)

Olivia Wilde, Harry Styles

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Harry Styles and Olivia Wilde met September 2020 after he replaced Shia Labeouf as the male lead of Wilde’s 2022 movie, Don’t Worry Darling. Styles and Wilde confirmed their romance in January 2021 after they attended Styles’ manager Jeffrey Azoff’s wedding together in Montecito, California, where Styles referred to Wilde as his “girlfriend” in his wedding speech, according to Us Weekly. A source told Us Weekly in July 2021 that Wilde and Styles were “smitten” over each other. “Olivia’s really smitten by Harry,” the insider said after the couple was photographed kissing in Italy. “He makes her really happy. It’s like he’s brought out this giddy side of her. The thing that works for them is that they don’t hide their relationship from the public. They don’t care who’s around watching them pack on the PDA.” Another source said of their relationship at the time, “Olivia and Harry have an ease to their relationship, they love and support each other, but also let each other be free and work on their own.” The insider also credited Wilde and Styles’ “constant communication when they’re not together” as a strength in their relationship. “Both of them respect the other’s work and never want to get in the way of each other,” the source said. Wilde and Styles went on to walk the red carpet together at the premieres of Don’t Worry Darling in Venice and New York City in September 2022. Wilde was also seen in the audience at several of Styles’ Love on Tour shows throughout 2022.

Confirmation of Styles and Wilde’s relationship came three months after news broke that Wilde and her then-fiance, Jason Sudeikis, had broken up after nine years of dating in November 2021. The former couple share two children: daughter Daisy Josephine and son Otis Alexander. A source told Page Six in July 2022 that Styles’ Don’t Worry Darling co-star, Florence Pugh, was upset over Wilde and Styles’ romance because of how soon it started after Wilde’s split from Sudeikis. “I can tell you for a fact that Flo seeing Olivia and Harry all over each other on set did not go down well as Olivia was still with Jason when she first hooked up with Harry,” the insider said. “Jason and the kids visited Olivia on set at the beginning a few times, so I think this all made people feel a little uncomfortable.” Sources also told Page Six at the time that Styles and Wilde’s romance was the cause of the director’s breakup with Sudeikis, claiming that Styles and Wilde’s affair had already been happening for a month by the time Sudeikis and Wilde ended their relationship.

Wilde called rumors she cheated on Sudeikis with Styles “complete horseshit” in a September 2022 interview with Vanity Fair. “Our relationship was over long before I met Harry. Like any relationship that ends, it didn’t end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic,” she said at the time. “We were raising two kids during lockdown, so we co-parented through that time. Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to NOT, because we could be better parents as friends who lived in different houses.” A source told People in October 2022 that Styles and Wilde were “thriving” despite claims from Sudeikis and Wilde’s former nanny that the director had cheated on her ex-fiance with the One Direction member. “Olivia is happy that Harry is around. All the drama is a lot and definitely affects her,” the insider said. “Olivia and Jason don’t have very much contact. When they do, it’s all about the kids. They co-parent as best as they can.” The source continued, “Harry and Olivia are great. They’re better than ever. They rise above this sort of thing all the time and they’re just moving forward with their relationship and are happy and thriving.”

On November 18, 2022, sources close to Harry and Olivia revealed that the two were “taking a break”. According to People, an insider said there was no bad blood between them but their schedules and priorities had begun to clash. “He’s still touring and is now going abroad. She is focusing on her kids and her work in L.A.,” says one source. “It’s a very amicable decision.” The insider continued: “They’re still very close friends. Right now, they have different priorities that are keeping them apart.”

Camille Rowe (2017 – 2018)

Camille Rowe

Image: Frazer Harrison/Getty Images.

Harry Styles and model Camille Rowe met in 2017 after they were introduced by their mutual friend, Alexa Chung. Soon after, the two were photographed at dinner together in Los Angeles. A day before their date, Rowe was asked in an interview with Glamour Paris about who she planned to send a text to that midnight, which she responded with: “To my boyfriend.” A source told The Sun in 2018 that Rowe met Styles’ family around the holidays before they spent New Year’s together in Los Angeles. “Camille’s come along at exactly the right point in Harry’s life,” the source said. “He’s had plenty of fun but seems to be content hanging out with her. They get on great. She’s laid-back and cool, plus she’s been really supportive of his career.” The source continued, “The relationship is still fairly relaxed, he’s hardly at the stage where they see each other every day. But Camille has also bonded with his sister Gemma and best pal Lou Teesdale, which is hugely important to Harry.”

News broke July 2018 that Styles and Rowe had broken up a month after she was seen at Styles’ final show on his Harry Styles: Live on Tour in Inglewood, California. Styles’ best friend, Tom Hull, told Rolling Stone in 2019 about how the split inspired Styles’ second studio album, Fine Line. “This breakup that had a big impact on [Styles].” Hull also told a story about when the singer saw Hull wearing a pair of slippers that Rowe (who he was “really cut up about” at the time) had given Hull. Though Hull and Rowe were “still close friends,” Hull recalled Styles having an issue with him wearing the slippers. “How could you wear those?” Styles asked Hull, according to the One Direction member’s friend. In the same interview, Styles also confirmed Fine Line was inspired by his personal life. “It’s not like I’ve ever sat and done an interview and said, ‘So I was in a relationship, and this is what happened,'” he said. “Because, for me, music is where I let that cross over. It’s the only place, strangely, where it feels right to let that cross over.”

In Fine Line, Styles also included a voicemail from Rowe at the end of the song “Cherry,” which seemed to nod to Rowe’s French background. “It got added in later on, and it felt so part of the song,” Styles told Apple Music at the time. “It just felt like it needed it. We’re friends and stuff, so I asked her if it was OK. And she was OK with it.” Fans also believe the lyrics to “Cherry” also seem to reference a celebrity couple with the name “Charry.” “Does he take you walking ’round his parents’ gallery?” Styles sings in the song, which fans believe is a reference to art gallerist, Theo Niarchos, who Rowe dated after him.

Kendall Jenner (2016)

Kendall Jenner, Harry Styles

Image: Terence Patrick/CBS via Getty Images.

Harry Styles and Kendall Jenner first sparked dating rumors in 2013 after they were photographed  together at the restaurant Craigs in West Hollywood, Los Angeles. A source told People at the time the two were just friends, as Jenner was dating rapper Young Jinsu at the time. “They’re just friends,” the insider said. Jenner also responded to the dating rumors in an interview with E! News at the time. No story, we’re friends. He’s cool,” she said. She also revealed that she had only met a few One Direction members at the time. “I haven’t met them all,” she said. “But the few I’ve met are amazing. They’re really, really nice guys.”

The two sparked dating rumors again in January 2014 when they were seen skiing and snowboarding together in Mammoth, California. “Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on,” a source told People at the time. “Harry was a gentleman and even offered to carry Kendall’s snowboard to the ski lift.” However, it wasn’t until January 2016, when Kendall’s older sister, Khloé Kardashian, confirmed the two were dating that the news was official. “They were hanging out together. Do I think they’re dating? Yes. 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,'” she told Entertainment Tonight at the time, using air quotes. “But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.” She continued, “I don’t know if they’ve had that talk yet.”

Styles and Jenner split, however, in April 2016 after People confirmed the model had been dating Los Angeles Lakers player Jordan Clarkson. By September 2016, however, a source told People that Jenner and Styles were giving their relationship another try. “He’s not going to settle down, and she understands that’s just the way he is,” the insider said. “She really likes him, but her heart’s not as invested.” The source also claimed the two were “not officially back together” but were “continuing to talk and see where things go.” and that Jenner was “hopeful” about the relationship but was “being more careful this time.” Though the relationship never became official again, Styles hinted to Rolling Stone in 2017 that his debut album was inspired by Jenner. . “She’s a huge part of the album,” he said. “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.” The two reunited at the 2019 Met Gala, which Styles hosted, and a 2019 episode of the The Late Late Show, which Styles guest hosted, though they were just friends at that point.  “I’m dying to know this. Which songs on your last album were about me?” Jenner asked Styles during a game of “Spill Your Guts.” In the end, Styles chose to eat cod sperm instead of answer the question.

Taylor Swift (2012)

Harry Styles, Taylor Swift

Image: David Krieger/Bauer-Griffin/GC Images.

Harry Styles and Taylor Swift sparked dating rumors in November 2013 when the “Love Story” singer started wearing a paper airplane necklace similar to the one the One Direction member wore. A month before, Styles called Swift a “real lovely girl” in an interview with Seventeen. “Honestly, she couldn’t be a sweeter person. She’s a great girl and she’s extremely talented,” he said. “[She’s] one of those people you meet [who’s] genuinely a nice person. Some people you meet and they are not as nice as you make them out to be, but she’s one of those people who’s really just amazing.”

The two went viral in December 2012 after they were photographed on a date in Central Park. A day after, One Direction performed at Madison Square Garden in New York City, which Swift attended the after-party for. That same month, news broke that the two were involved in a snowmobile accident on a ski vacation, which Styles needed stitches for. Us Weekly confirmed in January 2013 that Styles and Swift had broken up while on vacation in the Virgin Islands, where they were seen in a “heated argument.” The magazine also reported that Swift cut the trip short and flew back home to Nashville, Tennessee, while Styles continued his travels. In February 2013, fans thought Swift shaded Styles when she seemed to do an impression of an English accent while performing the bridge of her song “We Are Never Ever Getting Back Together.” “Ugh, so he calls me up and he’s like, ‘I still love you,'” she said. “This is just exhausting, you know? We are never, ever getting back together. Ever.”

In an interview with Rolling Stone in September 2014, Swift confirmed her song “Out of the Woods” from her album 1989 was about a snowmobile accent, though she didn’t specify Styles was also there. She also suggested the song “Style” was also about the One Direction. “We should have just called [the song], ‘I’m Not Even Sorry,'” she said. (She also wore a paper air plane necklace in the music video in February 2015.) In a Google Hangout interview in November 2014, Styles called himself “lucky” to be the rumored subject of Swift’s songs. “We always say that we write from personal experience, and I think everyone does. So, it would be hypocritical to say ‘Oh, you can’t write songs.’ And she’s really good, so, they’re good songs,” he said.

Styles spoke in depth for the first time about his relationship with Swift in 2017. “When I see photos from that day, I think, ‘Relationships are hard, at any age,’” Styles said, referring to his and Swift’s Central Park date in 2012. “And adding in that you don’t really understand exactly how it works when you’re 18, trying to navigate all that stuff didn’t make it easier. I mean, you’re a little bit awkward to begin with. You’re on a date with someone you really like. It should be that simple, right? It was a learning experience for sure. But at the heart of it — I just wanted it to be a normal date.” He continued of Swift’s songs about him, “I’m lucky if everything [we went through] helped create those songs. That’s what hits your heart. That’s the stuff that’s hardest to say, and it’s the stuff I talk least about. That’s the part that’s about the two people.” In 2017, Styles released his song “Two Ghosts” from his debut album, which fans believed to be about his relationship with Swift. “I think it’s pretty self-explanatory,” Styles said when asked about the meaning behind the song at the time. “It’s about sometimes things change and you can do all the same things and sometimes it’s just different.”

Caroline Flack (2011 – 2012)

Caroline Flack

Image: Lia Toby/Getty Images.

Harry Styles and Caroline Flack met in 2010 when Styles was a contestant on the United Kingdom version of The X-Factor, which Flack hosted. Flack later wrote in her autobiography, Storm in a C Cup, that it was obvious Styles liked her. “I already knew that he had a crush on me, he’d made it pretty obvious,” she wrote at the time. “He’d said it in magazines and he’d said it to friends.” The two started dating in 2011, though the relationship didn’t last long. Flack, who was 31 at the time, responded to the age difference between her and Styles, who was 17, in her book. “It began to go wrong when Harry was pictured coming out of my house one morning,” she wrote”And once that was out, it was open season.” She continued, “After that anyone could say anything. In the street people started shouting at me ‘pedophile’ and ‘’pervert.'” She explained that the two broke up once she started to receive death threats.

Flack was found dead in her home in North East London on February 15, 2020. The coroner’s office determined her cause of death was suicide. She was 40 years old. After her death, Styles seemed to pay tribute to his late ex by wearing a black ribbon on his suite while attending the 2020 Brit Awards, which were held the same month as Flack’s passing. His mother, Anne Twist, tweeted that month: “Heartbreaking #ripcarolineflack.”

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