Harry Styles Dating Timeline: Relationships From Taylor Swift to Taylor Russell and Beyond

Harry Styles

Harry Styles' dating timeline has inspired a lot of great music—and not just his own.

The erstwhile One Direction star's love life has been a rollercoaster since his X Factor days, and it's been under a microscope more than ever following the release of Taylor Swift's 1989 (Taylor's Version). Find out everyone we know Styles has dated so far, plus who he's linked to now.

Related: Harry Styles' Net Worth

Harry Styles Dating

Who is Harry Styles in a relationship with?

As of October 2023, Styles is reportedly dating actress Taylor Russell. The pair were first linked in June 2023, and he's since been spotted supporting at her performances of The Effect at London's National Theatre. Russell was also seen at stops on Styles' Love on Tour.

Now, for all the ladies he's loved before!

Who was Harry Styles' first girlfriend?

While we're not sure if she's his first-ever girlfriend, we do know that before he became famous on X Factor, Styles dated Felicity Skinner for about a year. She said he was a "good boyfriend" and that they met through mutual friends.

Did Harry Styles date Caroline Flack?

Styles was linked to X Factor host Caroline Flack in 2011 when he was 17 to her 31. Styles announced their split in early 2012, noting that it was a "mutual decision."

In Flack's memoir, she wrote of the relationship, "It was only when it became public knowledge that things turned sour. At the beginning it was all very playful. He joked about being attracted to older women. It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season. After that anyone could say anything. In the street people started shouting at me 'pedophile' and 'pervert.' "

Flack died by suicide in 2020.

Related: Watch a Throwback Harry Styles Audition for X Factor

Did Harry Styles and Jillian Harris date?

Styles and Bachelor Nation alum Jillian Harris didn't hook up, but she said that he did try!

Styles, then 18, reportedly approached Harris, 32, at a Los Angeles hotel in April 2012.

"He didn't know who she was and she didn't know who he was until later," Harris' rep told E! News. "He's really cute. Jillian thinks he's adorable but a little too young for her."

When did Taylor Swift and Harry Styles date?

Styles and Swift were rumored to first hit it off in March 2012, though they weren't rumored to be dating until that fall and were never spotted together publicly until that December. The pair had a whirlwind and dramatic romance chronicled in 1989 and 1989 (Taylor's Version), culminating in a split during a trip to the Virgin Islands, after which Swift left in a boat alone and memorialized in "Is It Over Now?".

Related: Taylor Swift's Dating History

Swift and Styles were widely believed to have been off and on, however, between March 2012 and their January 2013 split. And in their "off again" periods, Styles was linked to actress Emily Atack and Emma Ostilly, the latter of whom appeared in the One Direction music video for "Gotta Be You."

Styles and Swift reportedly had their first split after he was seen smooching Ostilly in paparazzi photos.

Atack initially said she and Styles were just friends, but later confirmed they'd had a fling but never got serious.

Related: A Complete Guide to Taylor Swift’s Purr-fect Companions—Her Cats!

How old was Taylor Swift when she dated Harry Styles?

Swift and Styles dated publicly when she was 22 and he was 18.

Related: Exactly Why Taylor Swift Is Re-Recording All of Her Old Albums

Who did Harry Styles date after Taylor Swift?

Styles' first public rebound after his split from Swift was with Kimberly Stewart, nepo baby of legendary singer Rod Stewart. The pair were spotted with then-33-year-old Stewart when he was 19 several times in early 2013.

Of course, there were several other romances since then!

When did Harry Styles date Kimberly Stewart?

Styles and Stewart were linked in early 2013.

How long did Harry Styles and Kendall Jenner date?

Styles had an on-again-off-again fling with Kendall Jenner. They were first photographed together in November 2013, though Jenner denied a romance at the time. However, by January 2014, they were spotted kissing, and they rang in Styles' 20th birthday together that February.

The romance appeared to cool temporarily, but they were spotted getting cozy together on a yacht in December 2015. Jenner's sister Khloe Kardashian said at the time that she believed they were dating, but wasn't sure it was serious. They weren't seen together again until April 2016, then again that September, when sources told PEOPLE they were trying to make more time to be together. That November, Styles attended Jenner's 21st birthday party, but their exchanges afterward appeared to be purely platonic, though warm and friendly.

When did Nadine Leopold and Harry Styles date?

Styles was spotted out to dinner with model Nadine Leopold in November 2014, and he was seen bringing balloons to her birthday party in January 2015. She attended his 21st birthday in February 2015, but they called it quits that March.

Did Harry Styles and Georgia Fowler date?

Styles was linked to model Georgia Fowler briefly in fall 2015 when he was spending time in New Zealand, where she's from. Fowler documented a game of Scrabble with Styles on her Snapchat (via The Daily Mail), but it didn't spell long-term. His song "Kiwi" was rumored to be about her, but she said in an interview that she doubted it.

Did Harry Styles date Tess Ward?

Styles was linked to British food blogger Tess Ward after he and Jenner split for a second time. They were first linked in May 2017, with sources telling The Daily Mail that they'd been on a number of dates by then. By that June, however, their romance fizzled, with Ward reportedly reuniting with an ex.

What happened between Camille Rowe and Harry Styles?

After his split from Ward, Styles was linked to model Camille Rowe. Rumors first emerged of a coupling in July 2017, but they weren't spotted together until that September. Rowe was seen at a number of Styles' concerts over the next year.

The pair split in 2018, but remained friends — and he got her permission to include a voicemail from her in his song "Cherry" from Fine Line.

How long were Harry Styles and Camille Rowe together?

Styles and Rowe were together for about a year.

What happened to Harry Styles and Olivia Wilde?

Styles met Olivia Wilde when she cast him in her film Don't Worry Darling in 2020. She and longtime partner Jason Sudeikis announced their split shortly afterward, and in January 2021, Styles brought Wilde as his date to a wedding.

Wilde was spotted seeing Styles several times during his Love on Tour tour, and she reportedly inspired his song "As It Was," which featured the lyric, "I don't wanna talk about the way that it was, leave America, two kids follow her, I don't wanna talk about who's doin' it first."

In the press cycle leading up to Don't Worry Darling's release in 2022, Styles didn't discuss his romance with Wilde, and the pair never posed together on red carpets promoting the movie. Wilde had slightly looser lips, telling Variety of her and Styles, "We both go out of our way to protect our relationship. I think it's out of experience, but also just out of deep love."

Wilde and Styles called it quits in November 2022 (incidentally shortly after Don't Worry Darling hit streaming on Max), with PEOPLE citing his international tour as a driver of the split.

Related: Everything to Know About Olivia Wilde and Harry Styles' Relationship

Did Harry Styles and Emily Ratajkowski date?

In March 2023, Styles was snapped smooching Emily Ratajkowski in Tokyo. A source told PEOPLE that Ratajkowski "hooked up with Harry, but they are not in touch every day."

Related: Emily Ratajkowski's Dating History

Did Harry Styles and Kiko Mizuhara date?

Hours after he was seen sucking face with Ratajkowski, Styles was spotted with Japanese model Kiko Mizuhara in Tokyo's Shinjuku district. The pair were rumored to possibly have dated in 2019. They reportedly attended a party together in March 2023, though it's unclear if their encounter was a romantic one.

Related: Taylor Swift and Joe Alwyn's Relationship Timeline

Who has Harry Styles dated the longest?

To date, Styles' longest relationship has been with Wilde. The pair dated for nearly two years.

Is Harry Styles engaged?

As of October 2023, nope!

Next, Find Out Taylor Swift's Boyfriend Travis Kelce's Dating History