Since his X Factor breakout in 2010, Harry Styles has gone from Directioner crush to full-blown global icon — with fans obsessing over everything from his fashion to his love life (and yes, even questioning his sexuality along the way).
The man’s roster of exes is wild: he’s dated the freakin’ Taylor Swift, had on-off flings with Kendall Jenner, and been linked to a lineup of Victoria’s Secret models and Hollywood it-girls: yes, some of the most talked-about celebs in pop culture have dated Mr. Harry Styles.
Basically, if you’ve been wondering what it takes to date Harry Styles, buckle up, because his love life reads like a rom-com scripted by Hollywood, complete with stadium tours and paparazzi plot twists.
Who is Harry Styles dating now?
Lately, rumor has it Harry’s been sparking romance with none other than Zoë Kravitz. The two have been spotted arm-in-arm in Europe and cozying up in London, leaving fans buzzing that this could be his most iconic pairing yet. More below!
Harry Styles Girlfriends in Order
Jump to:
- Caroline Flack
- Emma Ostilly
- Emily Atack
- Caggie Dunlop
- Taylor Swift
- Kimberly Stewart
- Cara Delevingne
- Nicole Scherzinger
- Ariana Grande
- Katy Perry
- Erin Foster
- Nadine Leopold
- Sara Sampaio
- Kendall Jenner
- Pandora Lennard
- Tess Ward
- Camille Rowe
- Kiko Mizuhara
- Olivia Wilde
- Emily Ratajkowski
- Taylor Russell
- Olivia Dean
- Ella Kenny
- Zoë Kravitz
Ex: Caroline Flack
Who is She? TV Presenter
Dated In: 2011
From the jump, Harry was lowkey crushing on Caroline, presenter of The X Factor, while he was on the show. The singer made no effort to keep his admiration a secret, as Caroline even said at the time, “I already knew that he had a crush on me, he’d made it pretty obvious as he’d said it in magazines and said it to friends.”
After the show, the pair started dating when Harry was 17 and Flack was 31. But once the news dropped, the internet and tabloids had a field day and it all went downhill for the lovebirds. Caroline got death threats and said: “We were both single, we got on well and we had a laugh. It was only when it became public knowledge that things turned sour.”
Sadly, in 2020 Caroline took her own life at 40, and Harry paid tribute to his late ex by wearing a black ribbon to the Brit Awards that year.
Rumored Ex: Emma Ostilly
Who is She? Model
Dated In: April 2012
Following his split from Caroline, Harry moved on to Victoria’s Secret model, Emma, who also appeared in One Direction‘s music video, Gotta Be You. While the stud denied that he was in a relationship with Emma, the pair were spotted locking lips after a night out in Auckland. And as soon as the news went public, Emma also received a number of threats, which then forced her to delete her Twitter account. I guess things ended right around that time.
Ex: Emily Atack
Who is She? Actress/ TV Presenter
Dated In: 2012
Harry had a short-lived romance with British actress and TV presenter, Emily Atack in 2012. The Inbetweeners star who is four years older than Harry (I’m noticing a trend here) only confessed in 2014 that they indeed shared a fling. Admitting that “We were never boyfriend and girlfriend,” Emily added that their relationship was never anything more than “a bit of fun.”
She did send the media into a storm when she tweeted in 2010, “Does Harry from One Direction have to be 16?”, proving from then that she had a crush on the young star.
Rumored Ex: Caggie Dunlop
Who is She? Reality TV Star
Dated In: July 2012
Another “older girl” in Harry’s dating history is Made in Chelsea star Caggie Dunlop who was five years his senior. The pair was first spotted getting friendly in a nightclub together in July 2012, and later exchanged some flirty messages on Twitter. Even the Sunday Mirror’s insider said there was “great chemistry between them,” but both parties denied there was anything between them. Things got so bad for Caggie, that fans even started showing up outside her parents’ house. “She got a bit freaked out,” her friend Millie said at the time.
Ex: Taylor Swift
Who is She? Pop Artist
Dated In: Dec 2012 – 2013
What a time to be alive…2012 when Harry Styles and Taylor Swift were freakin’ dating! Harry’s romance with Taylor Swift was the talk of the town when pictures first emerged of the pair taking a stroll in Central Park. Swifties and Directioners went into a frenzy, but sadly, the fairytale romance was short-lived and the celebrity couple split in 2013.
A year later, Harry finally addressed his relationship with Taylor during an interview with Rolling Stone, saying, “When I see photos from that day I think: Relationships are hard, at any age. 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.”
Oh and if you ever want to know how Tay and Harry felt about their relationship, go ahead and listen to Taylor’s Style and Harry’s Two Ghosts to get a better picture.
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Rumored Ex: Kimberly Stewart
Who is She? Model
Dated In: April 2013
Let’s be real—many celebs struggle with finding genuine connections in dating. Harry’s not the only one; even stars like Drake and Bad Bunny have faced the same challenge. In 2013, Harry had a brief romance with Rod Stewart’s daughter, Kimberly, but once again, he found himself struggling with the connection. Harry, 19, and a then-33-year-old Kimberly were spotted in West Hollywood dining with the whole of the Stewart clan, and sources even told E Online that he was “very cuddly with her.” Neither Harry or Kimberly confirmed or denied the hook-up, so let’s just assume it was all talk.
Rumored Ex: Cara Delevingne
Who is She? Model
Dated In: Sept 2013
While we really wished this one was true, sadly, it was all rumors. After watching The Book of Mormon together, it was speculated that the pair were romantically linked, and they even took a cheeky pic together behind the scenes of Cara’s fashion show. Even though a source told E Online that Harry and Cara were “seeing each other, casually,” Harry set the record straight. Reaffirming that he and Cara were nothing more than friends, he said: “She’s not my girl!”
Rumored Ex: Nicole Scherzinger
Who is She? Singer & TV Personality
Dated In: 2013
Harry slipped back into his old ways in 2013 when he supposedly dated yet another of his seniors. Nicole Scherzinger was 35 and Harry was 19 when rumors swirled of a short and secret romance. The Sun reported in 2015 that The Pussycat Dolls singer and Styles “had a dalliance at the end of the X Factor in 2013 and met up again early last year…They hooked up over three years later when Harry had matured and was a member of the world’s biggest band.” But nothing else came out of this controversial romance.
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Rumored Ex: Ariana Grande
Who is She? Pop Artist
Dated In: April 2014
Harry and yet another best-selling female artist was the talk of the town back in 2014. But turns out, this affair was nothing more than a rumor. The speculation came after Harry wrote a song for Ariana titled, Just a Little Bit of Your Heart. Fans instantly suspected the song was about the popstar herself, but Ari set the dating record straight during an interview with Australian radio show Smallzy’s Surgery, saying, “He is a very, very, very nice boy but I’m not like… He’s just a nice friend.”
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Rumored Ex: Katy Perry
Who is She? Pop Artist
Dated In: Sept 2014
This rumored fling was wild. Back in 2014, it was alleged that these famous faces were hooking up after being spotted at dinner together at Nobu. The tea was piping hot, especially considering Katy Perry’s fall out with Taylor Swift at the time. Was Katy dating Harry to get back at Taylor? The drama! Nothing ever came out of this…sadly.
Rumored Ex: Erin Foster
Who is She? Writer & Performer
Dated In: Oct 2014
After Harry and Erin were spotted at a pumpkin patch in 2014, the question on everyone’s mind was, has Harry got himself another cougar girlfriend? Erin, who was 32 at the time, also shared a meal with Harry (20), but this string of outings turned out to be “nothing serious.”
Ex: Nadine Leopold
Who is She? Victoria’s Secret Model
Dated In: Nov 2014 – March 2015
Harry was linked to Australian model Nadine Leopold for a few months between 2014 and 2015 after the two were spotted together on multiple occasions. Like many people his age, Harry seemed to be more into casual dating at the time. According to a Hollywood Life exclusive, “Nadine wanted a more serious commitment from Harry,” and ultimately decided to put an end to what she saw as his “game” playing.
Rumored Ex: Sara Sampaio
Who is She? Victoria’s Secret Model
Dated In: June 2015
After getting a taste for Victoria’s Secret models, Harry moved on to his next romantic endeavor: Sara Sampaio. While it was never made official, the pair did appear to enjoy a romantic night together. And get this: the model was papped leaving Harry’s New York hotel wearing the same outfit she entered in the night before. Nothing further came of this fling…
Ex: Kendall Jenner
Who is She? Model & Reality TV Star
Dated In: Jan – Sept 2016
What started off as a friendship, clearly surfaced into a love story. The former couple were snapped on numerous occasions, going back as early as 2014, but Kendall always said “we’re friends” and nothing more. Come 2016, and love was seriously on the cards. Harry and Kendall were captured cuddling on a yacht while celebrating the New Year together and her sister Khloe even told Entertainment Tonight, “Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend…”
Harry and Kendall rekindled things in late 2016, though a source said they were “not officially back together” and Jenner’s heart “wasn’t as invested.” Still, she was “hopeful,” while Styles later admitted in 2017 that Kendall was “a huge part” of his debut album.
Rumored Ex: Pandora Lennard
Who is She? Fashion Stylist
Dated In: Jan 2016
During his on-again, off-again relationship with Kendall, Harry was spotted leaving Pandora’s house, suggesting they’d spent the night together. Rumors even swirled that Harry had cheated on Kendall after a source told MailOnline, “We didn’t think anything would happen as Harry and Kendall are officially an item. This is gobsmacking.” Obviously nothing else came out of this wild story and Harry and Kendall continued their sweet romance.
Ex: Tess Ward
Who is She? Celebrity Chef
Dated In: May 2017
Harry’s dating history includes celebrity chef, Tess Ward. These two shared a brief romance in 2017 after enjoying a string of dates, but many critics claimed that Tess had an ulterior motive and just wanted good press. Proving everyone wrong, Tess split with Harry and got back with her ex. She’d even revealed to The Times that she’d been dealing with lots of hate mail following her fling with the Golden singer.
Ex: Camille Rowe
Who is She? Victoria’s Secret Model
Dated In: July 2017 – July 2018
Harry’s first long-term relationship was with Camille Rowe, a Victoria’s Secret model, who he was with for an entire year. the hitmaker even introduced the model to his family and Camille was spotted hanging out with Harry’s mom at one of his concerts — proper girlfriend material. However, things came to an end when the pair called it quits in 2018. Harry later confirmed his song Cherry was about her, which included a voicemail from Rowe at the end of the song.
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Rumored Ex: Kiko Mizuhara
Who is She? Model
Dated In: Jan 2019
After these two followed each other on Instagram, fans began suspecting a fling. Harry reportedly visited Kiko a ton during his visit to Japan, but the Japanese model put the rumors to bed when she tweeted, “It has been reported that Harry Styles and I have been in a relationship with him, but I have no relationship with him, and I have never met him…People believe what they want to believe rather than questioning reality.”
Ex: Olivia Wilde
Who is She? Actress
Dated In: Jan 2021 – Nov 2022
After one whole year of staying single, Harry officially bagged himself a Hollywood hottie. The singer, then-26, was spotted holding hands with then-36-year-old Olivia Wilde at his agent’s wedding in California. The couple showed more PDA on holiday and while working together on Don’t Worry Darling. But the relationship fizzled out in November 2022 due to their “different priorities.” This was Harry’s longest relationship to date, but turns out, it wasn’t meant to be.
Rumored Ex: Emily Ratajkowski
Who is She? Model
Dated In: March 2023
In March 2023, Harry and Emily Ratajkowski were caught locking lips in Tokyo, sparking major shipping energy. Sources said the two “have known each other” and were “friendly for a while.” But Emily later quipped, “There’s a million insane, inaccurate things about my relationships…, although, yeah… sometimes things just happen.”
Ex: Taylor Russell
Who is She? Actress
Dated In: July 2023 – May 2024
In mid-2023 Harry Styles and Taylor Russell quietly started dating — first spotted together in June in London and then caught out at his Vienna concert in July. Sources said their “energies work really well together,” and that “things are very serious.” But by May 2024, the pair had called it off after nearly a year together due to a “strain” in their relationship.
Rumored Ex: Olivia Dean
Who is She? Singer
Dated In: Aug – Sep 2024
Harry and British singer Olivia Dean stirred up rumors in mid-2024 after being spotted getting cozy at a Five Guys in London and later hanging out together at festivals. An insider told The Sun that they “have loads in common … and are enjoying getting to know each other out of the spotlight.” However, nothing more came out of this rumored hook-up.
Rumored Ex: Ella Kenny
Who is She? Producer
Dated In: June 2025
In June 2025, Harry was caught kissing producer Ella Kenny in the VIP section at Glastonbury, which blew up online. They seemed “in a spark in the moment” type of vibe, with a source saying she’s “different … down-to-earth … quite different from the stars Harry’s dated before.” It’s unclear if this was more than a festival fling.
Girlfriend: Zoë Kravitz
Who is She? Actress
Dated In: Aug 2025 – Now
Rumors between Harry, 31, and Zoë Kravitz, 36, have been heating up in summer 2025: spotted in Rome arm-in-arm, kissing quietly at Rita’s bistro in London, and he even met her dad, Lenny Kravitz. A source said “they’ve gone from 0-60” but that “there are no labels … it’s very new and fresh and they’re just having fun together.”
After being spotted with Zoë Kravitz, fans are kinda living for this duo — like, Harry + Zoë? That’s power-couple energy. One thing’s clear: Styles has a type, and it usually involves supermodels or women a few years older (no shade, just facts).
So, what do you think of Harry’s love life rollercoaster? Should he settle down with Zoë, or are you secretly rooting for a throwback rekindle?
Originally published in May 2020.
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