Harry Styles Dating History, Fans Wonder As His Love Life Remains A Mystery

Harry Styles’ love life has been a topic of constant speculation, from his time as a Swiftie to that steamy kiss with Emily Ratajkowski in Tokyo. His romantic history is frequently dissected, debated, and gossiped about.

Since splitting from Olivia Wilde in November 2022—amid the fallout from the infamous Don’t Worry Darling controversy, as reported by DeuxMoi—Styles has been living life at a slower pace, out of the spotlight.

His Love On Tour concluded in July 2023, leaving fans eager to know more about his personal life.

Since then, Styles has been spotted with Emily Ratajkowski, Taylor Russell, and Olivia Dean. However, he has kept quiet about the nature of his relationships with any of these women.

Olivia Dean (2024)

Styles was recently rumored to be linked with fellow British singer Olivia Dean. Fans began buzzing when the two were seen together at a Five Guys in St. Paul’s, London. A fan even tweeted about the sighting, which quickly went viral.

Though the images fueled speculation about a potential romance, it was later clarified that Styles and Dean are just good friends, possibly collaborating on new music. Regardless, the prospect of a musical partnership between the two has fans excited for what 2024 might bring.

Taylor Russell (2023–2024)

According to DeuxMoi, Styles and Bones and All actress Taylor Russell were reportedly dating as of early September 2023, though they were not exclusive at the time.

Despite the rumors, the pair didn’t shy away from the public eye. Styles attended the press night for Russell’s play The Effect at the National Theatre in London, and the two were later seen walking together in Brewer Street, further fanning the flames of gossip.

By mid-October, sources confirmed that their relationship had become more serious, with Styles reportedly “head over heels” for Russell.

In February 2024, Russell was even spotted wearing a Tiffany & Co. engagement ring, though it was on the wrong hand, which led to engagement rumors.

However, by May 2024, reports surfaced that the pair had ended things after a trip to Tokyo. According to sources, they decided to take some time apart, with Styles spending time in America while Russell remained in London.

Emily Ratajkowski (2023)

Four months after his split from Wilde, Styles was photographed kissing model Emily Ratajkowski on the streets of Tokyo. The passionate moment caused quite a stir, reportedly leading Wilde to cut ties with both Styles and Ratajkowski, who had been close friends.

Olivia Wilde (2021–2022)

Styles and Wilde’s highly publicized relationship began in January 2021 when they were seen attending his manager Jeffrey Azoff’s wedding together.

The couple’s romance reportedly blossomed while working on Don’t Worry Darling, and they were later spotted vacationing on a boat off the Italian coast. Wilde frequently attended Styles’ concerts, and the couple appeared stronger than ever by the summer of 2022.

However, following the drama-filled press tour for Don’t Worry Darling, the couple’s relationship reportedly became strained. In November 2022, a source confirmed that Styles and Wilde were “taking a break” from their relationship, citing busy schedules and geographical distance as factors.

Camille Rowe (2017–2018)

Styles’ relationship with French model Camille Rowe began in 2017 and lasted for about a year. Rowe served as a muse for Styles’ critically acclaimed album Fine Line, and in a revealing interview with Zane Lowe, Styles confirmed that his song “Cherry” was about one of his exes, featuring her voice at the end of the track.

Tess Ward (2017)

Following his second split from Kendall Jenner, Styles briefly dated British blogger and chef Tess Ward. The two were spotted together in May 2017, wearing matching shirts, which sparked dating rumors. However, their romance was short-lived, ending in June when Ward reportedly got back together with her ex-boyfriend.

Kendall Jenner (2013–2014)

Styles and Kendall Jenner’s relationship first made headlines in 2013 after they were seen dining together at Craig’s restaurant in Los Angeles.

They spent the new year together in Mammoth, California, and later vacationed in the Caribbean. In 2016, Jenner’s sister, Khloé Kardashian, hinted at their relationship in an interview, describing them as a couple, though neither Styles nor Jenner confirmed it at the time.

The pair briefly reunited in late 2016, with Styles attending Jenner’s 21st birthday. In an interview, Styles admitted that Jenner had been a major inspiration for his debut solo album, saying, “Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap.”

Taylor Swift (2012–2013)

Perhaps one of the most famous of Styles’ relationships was his brief romance with Taylor Swift. The two started dating in December 2012 and were seen together in Central Park. Their relationship ended after a holiday trip to the Caribbean in early 2013.

Fans continue to speculate that Swift’s hit song “Style” is about her time with Styles, noting the references to his trademark look and mannerisms.

Emily Atack (2012)

While still a member of One Direction, Styles was rumored to have had a brief fling with Inbetweeners actress Emily Atack.

Although neither party confirmed the romance at the time, Atack later described it as “a bit of fun” and said that the two had quickly gone their separate ways.

Caroline Flack (2011–2012)

Styles’ relationship with TV presenter Caroline Flack stirred controversy due to their 14-year age gap, with Styles being 17 and Flack 31 when they began dating.

The two met while Flack was hosting The Xtra Factor, but their relationship ended after a few months due to intense media scrutiny.

Felicity Skinner (2009)

Before fame, Styles had a relationship with Felicity Skinner when they were both teenagers. Skinner described him as shy but very romantic, saying their puppy love was sweet and that Styles had been her first love.

With a love life that’s as highly publicized as his music career, Styles continues to intrigue fans with his romantic entanglements.

Each of his relationships, past and present, offers a look into the private life of one of the world’s biggest pop stars.