A Complete Timeline Of Harry Styles' Relationships

The following article references suicide.

Heartthrob Harry Styles has undeniable talent and charisma that has helped him go from teen hopeful to international pop sensation, capturing the hearts of millions of fans. He's also captured the hearts of a number of fellow A-listers. Styles' most recent lover is actor and filmmaker Olivia Wilde, but this is just the tip of the iceberg when it comes to the former boy band member's A-list dating history.

Despite wanting to keep his private life private, the singer has been linked to quite a few celebrity beauties over the past few years. From cryptic song lyrics to late night rendezvous, Styles' love life has had its ups and downs. However, as far as we can tell, he sure seems to, as the song goes, treat his exes with kindness.

Want to know who he's dated? And do you want to get into all of his rumored romances and flings? We're here to break down the list. Let's dive into Harry Styles' relationship timeline.

When he was just 17 years old, Harry Styles competed on "The X Factor," where he would meet his first (and most controversial) celebrity girlfriend. Television host Caroline Flack was 31 when she started dating the teenaged Styles, and the couple's 14-year age gap caused a tornado of backlash amongst media and fans alike. Despite the drama, the couple were smitten. "I already knew that he had a crush on me, he'd made it pretty obvious. He'd said it in magazines and he'd said it to friends," Flack wrote in "Storm In a C Cup" (via People). "I've never felt I was much older than Harry anyway. I still feel 18 and probably act that way half the time." However, the scrutiny on and off line eventually took its toll. "In the street people started shouting at me 'pedophile' and 'pervert,'" Flack recalled. The pair eventually split on mutually good terms.

In February 2020, Flack died by suicide. Though Styles didn't make a public statement, the black ribbon he wore to the BRIT Awards was believed to be a symbol of mourning in honor of his late ex. As The Sun pointed out, Styles later performed wearing a badge reading "treat people with kindness," a reference to his own song as well as a presumed nod to a message Flack shared months before her death. Styles' mother also paid tribute to the late host on Instagram with a heartfelt poem (via The Mirror).

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

Soon after One Direction finished third on "The X Factor," the group really took off. As their popularity grew, paparazzi followed the five teens wherever they went — and Harry Styles was frequently caught getting his canoodle on. In April of 2012, Styles moved on from his romance with Caroline Flack by cozying up to American model Emma Ostilly. As reported by the Mirror, the two met on the set of One Direction's "Gotta Be You" music video, and seemed to be forming a closer relationship when they were spotted kissing after a date in New Zealand. At the time, an onlooker told the Mirror, ​​"They seemed very happy and relaxed and you could tell they have a history together. The pictures show they are still close." However, the steamy photos of their date immediately sent 1D fans into a frenzy. The stans attacked the model with abuse and threats on Twitter, causing Ostilly to delete her account altogether. To add salt to their wounds, before leaving the platform, Ostilly tweeted (via Mirror) a picture of herself and Styles and wrote, "Dinnnaa with harry styles."

All in all, Styles and Ostilly's fling didn't last long. Before long, Styles was spotted with another blonde American beauty.

In late 2012, Directioners and Swifties alike were shocked when rumors swirled of a romance between Harry Styles and Taylor Swift. Speculation began when Swift was spotted wearing a paper airplane necklace that matched one Styles frequently wore at the time. The two were then seen going out on a series of dates around NYC, including a romantic stroll through Central Park where they were all smiles. However, as Insider notes, after only two months, the couple reportedly broke up. In the years following, both Styles and Swift grieved through their music, with fans suspecting that Swift's "Style," "Out Of The Woods," and "I Knew You Were Trouble" are about her boybander ex. As for Styles, fans have wondered if certain solo songs were inspired by this relationship, as well as whether or not 1D's track "Perfect" is about Swift. With lyrics like "And if you're looking for someone to write your breakup songs about / Baby, I'm perfect," it's hard to deny the connection.

That said, the two exes sure seem to respect one another. As Styles said of Swift on "The Howard Stern Show in 2020, "She's a great songwriter. So at least they're good songs." The pair publicly reunited for the first time at the 2021 Grammys, and in May 2022, Styles delighted fans by singing Swift's "22" at a London concert, squashing all speculation about a potential beef between the singers.

Soon after his 2013 split from Taylor Swift, Harry Styles found himself in the arms of another American belle: model and reality star Kendall Jenner. After the pair were photographed getting dinner in West Hollywood and leaving in Styles' car, both parties promptly denied any romance. The speculation only grew when the two were pictured getting close at the British Fashion Awards and skiing in California, but they still never confirmed anything. In December 2015, Styles and Jenner were spotted ringing in the New Year on Ellen DeGeneres' yacht, where a source told People, "They had fun then, but things never got serious." The couple later reconnected to rekindle things, and Jenner's sister Khloé Kardashian told ET that she believed they were an item on some level.

Jenner and Styles have always kept their relationship private, so it feels safe to assume we'll never know the full story. Nevertheless, they still seem to be friendly after their romance. In perhaps their most iconic reunion, Styles and Jenner had the chance to publicly rehash their relationship when Styles hosted "The Late Late Show" in 2019. The exes played the infamous "Fill Your Guts Or Spill Your Guts" game, where at one point Jenner asked, "Which songs on your last album were about me?" The audience roared in applause, but Styles chose to eat cod sperm instead of answering. The undeniable chemistry between these two still had us wondering if there were any lingering feelings, but Styles and Jenner just seem to be good friends.

In the midst of his on-and-off relationship with Kendall Jenner, Harry Styles was rumored to be dating Victoria's Secret model Nadine Leopold. According to Us Weekly, the two met through Styles' close friend and CAA agent Jeff Azoff and immediately hit it off. Though they were never exclusive, the pair allegedly spent tons of time together, even celebrating Leopold's birthday together that year. In spite of their close relationship, it didn't appear that Styles was looking for anything serious: "Harry is having a good time being a young rock star," a source told Us in early 2015. "You will know he has a girlfriend when he steps out on the red carpet with one. Until then, he's having fun and enjoying life."

Ultimately, the model reportedly dumped Styles because of this inability to commit. "Nadine wanted a more serious commitment from Harry," a source close to Leopold told Hollywoodlife.com. "She felt like he needed to make more of an effort to see her. She just didn't feel like he was taking their relationship seriously enough, and basically she doesn't have time for any games in her life." Though their fling was short-lived, a source told Heat magazine (via Independent.ie) that he apparently wasn't happy about the breakup.

Ah, another rumored relationship. In 2015, Harry Styles reportedly engaged in a very brief relationship with Victoria's Secret angel Sara Sampaio. By brief, we mean brief: According to The Sun, after a night of partying in Manhattan, the stunning duo were snapped hugging and kissing goodbye outside of Styles' New York hotel. But that was not the end of this little story. As tipster told E! News, "Then she came back and slept over. Then she left at 11 a.m. in the same clothes." The Sun's source shared a similar account, telling the tabloid, "There was definitely chemistry there as they hugged and kissed each other when she left but everyone thinks something was up as she came back and they left so soon after each other the next morning."

At the time, Styles was making efforts to keep his relationships out of the media, so Sampaio was subtle about their friendship. "Discretion and privacy are absolutely key to [Styles] as he's been burned by some relationships. By all accounts, he trusts Sara," a source of The Sun's said. Now, we don't want to jump to conclusions, but was this more of a one night of fun situation? The two were never seen together again... but maybe they just had scheduling issues.

Harry Styles and model Georgia Fowler enjoyed an intimate holiday together in Fall 2015. According to The Sun (via Mirror), Styles booked a suite in the Babington House hotel for the romantic getaway, which included a private garden. A source told The Sun, "Harry wanted to spend some quality time with Fowler away from prying eyes. They kept to themselves and mostly spent their time in their room and garden, ordering food to the room instead of eating in the restaurant." According to J-14, Fowler posted a sneaky video of Styles playing scrabble on their romantic vacay — allegedly without his consent — sending One Direction fans into a frenzy. Fowler faced even more backlash when the media accused her of cheating on her ex-boyfriend with Styles.

Later, when Styles released the song "Kiwi" from his self-titled album, rumors swirled that the track was about the pair's London holiday. Per Grazia, when she was asked about the track on Australia's "The Morning Show," she replied, "Ah, don't really know anything about it." And as far as the song lyric "I'm having your baby it's none of your business" is concerned, she quipped, "I definitely don't have a baby!" Fowler continued, "The song's all about [having a baby] so I think it's highly unlikely [it's about me]."

In May 2017, Harry Styles was linked to author and food blogger Tess Ward. According to The Sun, Styles and Ward, who is best-known for her numerous cookbooks, bonded over their mutual love of fashion and food. Things got romantic quickly between the two, with a source telling Us Weekly, "They met through mutual friends and are really into each other." Soon after rumors of their romance hit the tabloids, Ward's previously well received cookbook "The Naked Diet" was bombarded with negative reviews — presumably from upset Harry Styles fans. Thankfully, some had Ward's back. "It's 'fans' like that that make us all look like nutballs. It's so childish," one fan tweeted in her defense (via The Sun).

Later, Ward was photographed wearing a floral Gucci shirt similar to one Styles wore four days before, raising suspicions she borrowed the top from the singer. After two months of drama, Styles and Ward split. A source claimed to The Sun,"Tess realised she still had feelings for her ex after splitting from him to date Harry and has apologised to him for her romance with the singer." She wasted no time reuniting with her ex after ending things with Styles. Ward later told The Times (Via E! News) that she was forced to delete social media due to the overwhelming hate she received, but refuses to confirm the relationship directly. "I literally don't have anything to say about that," she said, before her publicist interjected, "My clients don't talk about their personal lives." 

Next up, we have Camille Rowe. The French Victoria's Secret model dated Styles from 2017 until 2018, and as noted in a 2019 Rolling Stone profile, their breakup hit hard. As the in-depth story notes, the couple dated for about a year, with their relationship inspiring numerous tracks on Styles' sophomore album. "Falling," for example, highlights going through a difficult relationship, while "Cherry" is about missing a special someone and features a sweet voicemail from a mysterious French woman. "Watermelon Sugar" has also been rumored to be about Rowe because, as the model shared with Elle, "In Watermelon Sugar" by Richard Brautigan is one of her favorite books. 

Though Styles has never spoken about the relationship directly, in aforementioned Rolling Stone chat, he revealed he was inspired to read more by a former lover. "Reading didn't really used to be my thing. I had such a short attention span," he explained. "But I was dating someone who gave me some books; I felt like I had to read them because she'd think I was a dummy if I didn't read them." In his album track "Falling," Styles also alludes to cheating on a partner, so many suspect that this was the reason for the couple's split in July 2018. 

The following year, dating rumors sparked between Harry Styles and Japanese-American model Kiko Mizuhara after they followed each other on Instagram. As reported by the Daily Mail, the two apparently met when Styles was jet-setting back and forth to Tokyo over the course of a few months. Mizuhara initially denied knowing the singer, tweeting, "[It's been] reported that Harry Styles and I have been in a relationship, but I have no relationship with him, and I have never met him. The world is full of fake news."

However, as Seventeen noted, Mizuhara was spotted celebrating Styles' birthday with him in February 2019. The event took place at a karaoke bar, where Mizuhara was recording singing into a mike, and later, she and Styles were spotted having fun together in a video posted by "Queer Eye" star Bobby Berk. Alas, that seems to be the long and short of whatever did or didn't happen between the two.

Finally, we have Olivia Wilde. Harry Styles and Wilde connected while working together on the latter's feature film "Don't Worry Darling" in late 2020, soon after she split from her longtime fiancé, Jason Sudeikis. Styles and Wilde were first photographed together as a couple in early 2021. According to People, the two connected on the movie's set and were reportedly spotted hanging out in her trailer. At the time, Wilde had only good things to say about the pop star, telling Vogue, "To me, he's very modern, and I hope that this brand of confidence as a male that Harry has — truly devoid of any traces of toxic masculinity — is indicative of his generation and therefore the future of the world."

The two continued to praise each other, with Wilde frequently complimenting Styles' acting chops on her Instagram. The rumored relationship was pretty much confirmed when the stars were spotted smooching on a yacht in Italy that summer, but both continued to play coy.

When his relationship with Wilde came up on a May 2022 episode of "The Howard Stern Show" (via People), Styles didn't get personal. "I had a wonderful experience being directed by Olivia. I think there is something that obviously... acting is very uncomfortable at times," he said. "Being able to trust your director is a gift." And in the January 2022 issue of Vogue, Wilde didn't say anything too specific about Styles, but she did state, "I'm happier than I've ever been."