Harry Styles relationship timeline: From Taylor Swift to Olivia Wilde

Harry was then linked to model US Emma Ostilly in 2012, who he was snapped kissing on a night out in 2012, although he denied rumours they were dating.

Taylor Swift

Styles began dating pop star Taylor Swift in late 2012 when he was 18 and she was 22. They were photographed while on their second date in December, but the relationship did not last long.

Then, of course, there was Taylor Swift, who he was linked to for a few months between 2012 and 2013.

Taylor Swift and Harry Styles were first linked in March 2012 and later split up in January 2013.

Neither Taylor or Harry have ever spoken publicly about that time two of the world’s most popular teen stars were in love, but with Styles moving into a new chapter as he begins a solo career, it seems he’s ready to talk about Taylor. Harry admitted the attention on them was tough. “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 [fame and media attention] 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.”

As for what he thinks about Taylor’s multiple references to him in Style and throughout her 1989 album, Harry was modest, but clearly flattered.

“I mean, I don’t know if they’re about me or not…but the issue is, she’s so good, they’re bloody everywhere,” he said, adding, “I write from my experiences; everyone does that. I’m lucky if everything [we went through together] helped create those songs. That’s what hits your heart.”

Asked if he’s ever given Swift the Harry Styles tick of approval on the songs, he said “Yes and no,” which might be the most frustratingly vague answer of all time. “She doesn’t need me to tell her they’re great,” he continued. “They’re great songs … It’s the most amazing unspoken dialogue ever.”

“Amazing unspoken dialogue” is a much kinder way of describing what it’s like for Taylor Swift to immortalize your relationship in song compared to John Mayer, who said the track she penned about him was “a lousy thing to do”.

Harry’s willingness to open about Taylor’s writing about him could be because Styles also draws on his personal life when writing lyrics.

“Certain things don’t work out. There’s a lot of things that can be right, and it’s still wrong. In writing songs about stuff like that, I like tipping a hat to the time together.

“You’re celebrating the fact it was powerful and made you feel something, rather than ‘this didn’t work out, and that’s bad.’ And if you run into that person, maybe it’s awkward, maybe you have to get drunk … but you shared something,” he says.

“Meeting someone new, sharing those experiences, it’s the best sh*t ever. So thank you.”

Taylor’s song Out Of The Woods and One Direction’s hit Perfect were apparently inspired by the relationship – although the pair never concretely confirmed these rumours.

Kendall Jenner

Hazza’s also been linked to Kendall Jenner, with rumours that the pair were dating first starting up in late 2013.

In 2013, Styles was linked to model Kendall Jenner. They sparked rumours of a reconciliation two years later while on a yacht in Anguilla. They reportedly dated on-and-off until 2019, and now consider each other “good friends”.

They were snapped enjoying a string of dates in New York, LA and London, but their brief romance reportedly ended after just three months.

In December 2019, the rumours ramped up again when the pair flirted during an appearance on The Late Late Show.

Caitlyn Jenner confirmed the pair had dated in 2020 but didn’t go into specifics about when, or why they parted ways.

In November 2022, Jenner, joined by her sister Kylie Jenner and good friend Hailey Bieber, watched Styles perform at one of his concerts.

Nicole Scherzinger

In late 2013, Styles reportedly had a fling with Pussycat Dolls singer Nicole Scherzinger, who was a guest judge on The X Factor in 2010 when One Direction was formed. She was 16 years older than Styles, who was 19 at the time.

Interestingly, Scherzinger deserves most of the credit for forming One Direction. In recently released footage from the show that was left on the cutting room floor, it was revealed to be the Pussycat Dolls lead singer who suggested Styles and his band mates, who all independently auditioned for The X Factor in 2010, would make a good boy band.

Nadine Leopold

Not much is known about this relationship, but Styles was spotted with Australian model Nadine Leopold a number of times from 2014 until 2015.

Sara Sampaio

The One Direction star was seen kissing Portuguese model Sara Sampaio in June 2015. Styles and the Victoria’s Secret model spent the evening together at a hotel in New York City.

Georgia Fowler

Styles and New Zealand model Georgia Fowler were linked in October 2015 and spent time together at a suite in Babington House hotel in Somerset, England.

According to a source at the hotel, the pair kept to themselves.

“Harry wanted to spend some quality time with Georgia away from prying eyes,” they told The Sun.

Fans believe Styles’ song Kiwi is about Fowler, but she has denied this, telling journalists, “I don’t really know anything about it – definitely didn’t have a baby. That’s what the song’s all about so I think it’s highly unlikely.”

The song includes the lyric, “I think she said ‘I’m having your baby, it’s none of your business.”

Fowler initially sparked the dating rumours with Styles after sharing a video playing Scrabble with the singer on her Snapchat. Styles was wearing a fluffy bathrobe in the clip.

Tess Ward

Styles reportedly dated food blogger Tess Ward in May 2017 for a few weeks after meeting through mutual friend

Camille Rowe

The My Policeman star was first spotted with French model Camille Rowe at a Fleetwood Mac concert in New York City in July 2017. They dated for a year before ending thing

Harry then dated Victoria’s Secret model Camille Rowe for just over a year, before they split in July 2018.

In August 2019, Styles’ friend and collaborator Tom Hull told Rolling Stone that their split “had a big impact on him.” He had a whole emotional journey about her, this whole relationship,” Hull said. “But I kept saying, ‘The best way of dealing with it is to put it in these songs you’re writing.’”

Fans were convinced his 2019 song Cherry features a voicemail message from Camille (Styles’ song Cherry is about Rowe and features a voicemail from her at the end of the track).

Olivia Wilde

Fans were more than surprised when the former One Direction singer was spotted hand in hand with the actress and director Olivia Wilde, 39.

The pair were first seen at a friend’s wedding in January 2021.

Spending almost two years together, the famous faces put on a romantic display all over the world as Harry took his music on tour.

However, they called it quits in November of last year and a source told People: ‘He’s still touring and is now going abroad. She is focusing on her kids and her work in LA. It’s a very amicable decision.’

Yan Yan Chan

Styles was linked to uber-cool Aussie model Yan Yan Chan, 28, following his anticipated Sydney show in March.

Per multiple reports, the As It Was singer privately messaged Chan to invite her to an afterparty at his Sydney show on March 4, 2023.

The pair reportedly enjoyed a private getaway together during his time in the city, with the pair reportedly meeting in Byron Bay.

Emily Ratajkowski

Just four months after he split from Olivia, the singer was filmed sharing a sloppy snog with model and actress Emily. It appears that Emily Ratajkowski is “friendly” with Harry Styles’ ex Olivia Wilde.

Harry Styles Named Emily Ratajkowski His Celeb Crush Years Before PDA – The “Golden” singer was recently spotted locking lips with the model in Tokyo, as seen in a video posted by the Daily Mail on March 25. But way before they were seen sharing a kiss in Japan, Harry voiced admiration for Emily.

It’s unclear how he linked up with the mother-of-one, 31, in the city and if they are hoping to pursue their relationship further.

Ratajkowski wasn’t the only model Styles has been spotted with in Japan this week. The Medicine singer was also snapped hand in hand with 32-year-old American Japanese model, Kiko Mizuhara.

The “Gone Girl” actress bore a striking resemblance to Styles’ ex Kendall Jenner, whom he dated on and off for years.

“I mean she does look like Kendall,” one user noted, while dozens of others commented on Styles’ apparent manifestation powers.

The throwback clip came to light shortly after Ratajkowski, 31, and Styles, 29, were seen locking lips on the streets of Tokyo.

Fast forward years later, and Harry and Emily have been captured packing on some serious PDA. At the time, the pair were seen making out while standing behind a vehicle in Tokyo. Harry and Emily were also captured dancing together on the street. The “As It Was” singer was captured wearing a white shirt with a black jacket and matching pants, while the High Low with EmRata podcast host was seen sporting a pink and black jacket and a long black skirt.

MARKMEETS News reached out to Harry and Emily’s reps for comment, but did not hear back.

Right now, it seems Mr Styles is officially holding onto his single card but watch this space!