Harry Styles’ dating history has kept the paparazzi on their feet for years now, and with such A-listers in the mix, it is easy to see why.
While the internet is rife with speculation about Harry Styles and Zoë Kravitz, we take a deep dive into the past to explore the star-studded list of his previous romances and the events leading up to this latest buzz.
One of his most famous romances was with Taylor Swift back in 2012. Though brief, their relationship became iconic, inspiring hit songs and leaving behind a trail of paparazzi snapshots that still resurface to this day. After all, how could we ever “shake it off”?
Soon after, Harry Styles was linked to Kendall Jenner. First seen together in 2013, their rumoured on-and-off romance spanned several years, peaking with their viral yacht photos in 2016. Though neither officially confirmed the relationship, the pair remained a fan-favourite topic.
However, his most significant relationship in recent years was with actress and director Olivia Wilde. The pair began dating in 2021 during the filming of Wilde’s Don’t Worry Darling (2022) and quickly became one of Hollywood’s most talked-about couples. Their romance played out under intense public scrutiny before they amicably parted ways in 2022.
And now, speculation is swirling around a potential romance between Harry Styles and actress Zoë Kravitz. While things appear to be in the very early stages and nothing has been officially confirmed, whispers of the two spending time together, along with a handful of candid photographs, have stirred plenty of excitement. It seems we may be witnessing the beginning of yet another intriguing chapter in Harry Styles’ ever-evolving dating history.
No wonder so many famous romantic fanfictions about him exist, with some even being turned into movies.
Harry Styles’ dating history: All the ladies the One Direction heartthrob has romanced
Caroline Flack: 2011
Taylor Swift: 2012-2013
Kendall Jenner: 2013-2014, 2015-2016
Nadine Leopold: 2014-2015
Georgia Fowler: 2015
Tess Ward: 2017
Camille Rowe: 2017-2018
Olivia Wilde: 2021-2022
Emily Ratajkowski: 2023
Taylor Russell: 2023-2024
Ella Kenny: 2025
Zoë Kravitz: 2025-present
Caroline Flack (2011)
How they met: Set of The X Factor
Profession: TV presenter
Harry Styles was linked with The X Factor presenter Caroline Flack shortly after he competed on the UK show. However, right from the beginning, their age gap became a point of contention under the paparazzi’s gaze. The former One Direction member was 17, while Flack was 31 at the time; nonetheless, they decided to give it a shot.
Later, in her autobiography, Storm in a C Cup: My Autobiography, Flack wrote about Styles, “I already knew that he had a crush on me; he’d made it pretty obvious.”
However, in February 2020, Caroline Flack passed away after struggling with mental health issues. Styles paid tribute to her by wearing a black ribbon to the Brit Awards and even performed wearing a badge that read, “Treat people with kindness”.
Taylor Swift (2012-2013)
How they met: At the 2012 Nickelodeon Kids’ Choice Awards
Profession: Singer-songwriter
Today, Taylor Swift is engaged to her partner, who finally got down on one knee and popped the question. But long ago, Taylor Swift dated Harry Styles, and the world knows how that turned out.
Although this chapter in Harry Styles’ dating history wasn’t the longest, it did inspire some chart-topping pop music. He and Taylor Swift met at the Nickelodeon Kids’ Choice Awards in March 2012, and were soon spotted together — at concerts, on dinner dates, trips, and more. However, they reportedly broke up in January 2013.
While neither of them addressed the breakup, it is rumoured that several of Swift’s songs from 1989 are about Styles. Speaking to Rolling Stone in 2017, Styles opened up about the relationship, saying he learnt a lot from it, especially how to be cautious when photographed in public: “When I see photos from that day [of visiting Central Park together], I think: Relationships are hard, at any age.”
He also said, “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.”
Styles addressed songs Swift allegedly wrote about him, saying, “She doesn’t need me to tell her they’re great. They’re great songs.”
Kendall Jenner (2013-2014, 2015-2016)
How they met: Unknown
Profession: Model
Next on Harry Styles’ dating history is Kendall Jenner. They were first snapped together in 2013, and rumours of their alleged romance began almost immediately. However, both denied anything. Still, for eagle-eyed fans, it was hard to believe otherwise, as the pair went on a winter holiday together in early 2014 and even celebrated his birthday in February. Reports later stated that they broke up shortly afterwards.
It was again in December 2015 and early 2016 that the two rekindled their romance, with Page Six reporting that they were seen enjoying cosy moments together on New Year’s Eve. The outlet quoted Khloé Kardashian saying to Entertainment Tonight, “They were hanging out together”. She added, “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.’ But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.”
However, this time too, things didn’t last long, and they have remained friends since.
Nadine Leopold (2014-2015)
How they met: Unknown
Profession: Model
After things fizzled out with Kendall Jenner in 2014, Styles was linked to UK-based model Nadine Leopold. Neither of them confirmed the relationship, but from late 2014 to 2015, they were spotted together several times and even celebrated the “As It Was” singer’s 21st birthday together.
Georgia Fowler (2015)
How they met: Unknown
Profession: Model
His romance with Fowler is yet another major highlight in Harry Styles’ dating history. The New Zealand-native posted pictures of them together on Snapchat while Styles was in her country. But when he returned home, it marked the end of their short-lived romance.
While Styles’ 2017 song “Kiwi” was speculated to be about her, Fowler told The Morning Show hosts Larry Emdur and Kylie Gillies, “Ah, don’t really know anything about it. I definitely don’t have a baby! The song’s all about [having a baby], so I think it’s highly unlikely [it’s about me].”
Tess Ward (2017)
How they met: Unknown
Profession: Food blogger
Moving beyond models and singers, Harry Styles was rumoured to be dating food blogger Tess Ward in 2017. According to The Sun, the two enjoyed a “string of dates” and had been spotted together in London on the weekends. The duo was also spotted together at the Audi Polo Challenge in Ascot in May, where she reportedly wore his Gucci shirt.
However, they parted ways in June after she got back with her ex.
Camille Rowe (2017-2018)
How they met: Unknown
Profession: Model
Another one of Harry Styles’ most significant romances was with French-American Victoria’s Secret model Camille Rowe, a relationship he openly acknowledged. The pair dated for about a year, with Rowe even reportedly meeting his parents. They were last spotted together in July 2018.
Styles later revealed his song “Cherry” was about an ex, admitting to Zane Lowe (via Metro), “I wanted it to reflect how I felt then. I was feeling not great.” He added, “Because you get petty when things don’t go the way you want it. There’s parts that’s so pathetic.” The track features a voicemail from Rowe.
Olivia Wilde (2021-2022)
How they met: On the set of Don’t Worry Darling
Profession: Actor-director
If you are surprised by this chapter in Harry Styles’ dating history, let us remind you that Olivia Wilde had cast him in her sci-fi thriller Don’t Worry Darling in 2020. She had recently split from her fiancé, Jason Sudeikis, with whom she shares two children. By January 2021, photos of Styles and Wilde sharing cosy moments went viral, sparking dating rumours.
Wilde praised Styles on Instagram, writing, “Little known fact: most male actors don’t want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles.” She also wrote, “Enter: @harrystyles, our ‘Jack’. Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold centre stage as our ‘Alice’, but he infused every scene with a nuanced sense of humanity.”
She later told Vogue, “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. 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.” Although Styles kept the relationship private, they travelled extensively, and the paparazzi followed them everywhere.
The couple dated for nearly two years before amicably splitting in November 2022.
Emily Ratajkowski (2023)
How they met: Their common circle
Profession: Model
Back in the day, Styles had named Ratajkowski as his celebrity crush, and in 2023, the two were photographed kissing in Tokyo.
In 2023, a source told People that the pair had been “friendly for a while.” They added, “Harry and Emily know each other,” and noted that Ratajkowski was also friendly with Olivia Wilde. However, Ratajkowski told Vogue, “There’s a million insane, inaccurate things about my relationships [that are said].”
She did not approve of the way the media pitted her against Wilde.
Taylor Russell (2023-2024)
How they met: Unknown
Profession: Actor
Amid all the high-profile names, Harry Styles’ dating history also features Canadian actress Taylor Russell. They were first spotted together in London in June 2023 before she attended his Vienna concert in July. By September, photos of them holding hands surfaced, and sources claimed the pair was “very serious.”
One insider told US Weekly in October, “Harry is head over heels for Taylor and loves spending as much time with her as he can… Things are very serious, and Harry definitely sees a future with Taylor.” They were seen together at several events and travelled frequently despite their busy schedules.
However, after nearly a year together, the couple split in May 2024 following a “rough patch” during their Japan trip.
Ella Kenny (2025)
How they met: At the 2025 Glastonbury Festival
Profession: Content creator
Yet another speculation that garnered immense fan attention was Harry Styles’ alleged link-up with Ella Kenny. When internet sleuths and sharp-eyed fans spotted the singer sharing a moment of public affection with a so-called “mystery woman” at the 2025 Glastonbury Festival, they were quick to identify her as Ella Kenny.
She’s a content creator in the music industry and reportedly ran into Styles in the VIP section, accompanied by her friend, stylist Jessica Skeete-Cross, whose clients include Robert Pattinson, Cara Delevingne and Taylor Russell.
Zoë Kravitz (2025-present)
View this post on Instagram
How they met: Connected while in Europe
Profession: Actor
Now, let’s talk about the most recent addition to Harry Styles’ dating history.
While Styles and Zoë Kravitz have been spotted together in London, enjoying cosy moments, no official confirmation has been made. On 26 August, US Weekly quoted a source saying, “Zoë and Harry were both in Europe for work-related things and connected to meet up and hang out.” “They had met before and had kept in touch,” they added.
After Kravitz’s split from ex-fiancé Channing Tatum in 2024, she was linked to Austin Butler before being spotted with Styles. Only time will tell where this romance with the former One Direction member is headed.
(Hero and Featured image credit: Harry Styles/ Instagram)
