Harry Styles Dating History: A Complete Timeline

Harry Styles Dating History: A Complete Timeline

Harry Styles, the British heartthrob and former One Direction member turned solo artist, has captured the hearts of millions with his charm, talent, and distinctive style. Over the years, fans have followed his career closely, but perhaps nothing has piqued their interest more than his dating life.

From high-profile romances to rumored flings, Styles has kept the tabloids buzzing. Let’s take a stroll down memory lane and explore the complete timeline of Harry Styles’ dating history.

Felicity Skinner


Starting in his teenage years, Harry Styles dated Felicity Skinner, courtesy of a mutual friend. These two teenagers embarked on a romantic journey, even though they resided in separate cities. Their relationship endured for nearly a year before gradually fading away.

Caroline Flack


LONDON, ENGLAND – JUNE 07: Caroline Flack arrives for the Glamour Women Of The Year Awards on June 7, 2016 in London, United Kingdom. (Photo by Mike Marsland/Mike Marsland/WireImage)

Styles’ first publicly known relationship was with Caroline Flack, a British television presenter who was 14 years his senior. The couple met in 2011 when Styles was just 17 years old, and they began dating a few months later. Their relationship sparked controversy due to their age difference, but they remained together for nearly a year before splitting in 2012.

Taylor Swift


Harry Styles
NEW YORK, NEW YORK – NOVEMBER 12: Taylor Swift attends the “All Too Well” New York Premiere on November 12, 2021 in New York City. (Photo by Dimitrios Kambouris/Getty Images)

Harry Styles and Taylor Swift’s whirlwind romance created headlines worldwide. The two musicians dated briefly in late 2012 and early 2013, producing a few catchy songs rumored to be about their relationship. Their relationship was short-lived, lasting just a few months, but it was one of the most talked-about celebrity relationships of the year. Despite the breakup, they’ve remained friends and supportive of each other’s careers.

Kendall Jenner


Harry Styles
DUBAI, UNITED ARAB EMIRATES – JANUARY 21: Kendall Jenner attends the Grand Reveal Weekend for Atlantis The Royal, Dubai’s new ultra-luxury hotel on January 21, 2023 in Dubai, United Arab Emirates. (Photo by Kevin Mazur/Getty Images for Atlantis The Royal)

Styles’ relationship with reality TV star and supermodel Kendall Jenner was marked by secrecy. The couple were on-and-off for a few years, and were often seen together at public events and parties. Although they never confirmed their romance, paparazzi photos and social media hints led fans to speculate about their relationship.

Nadine Leopold


Harry Styles
VENICE, ITALY – SEPTEMBER 02: Nadine Leopold attends the “Bones And All” red carpet at the 79th Venice International Film Festival on September 02, 2022 in Venice, Italy. (Photo by Dominique Charriau/WireImage)

In 2014, Styles began dating Nadine Leopold, the Australian model. The couple were together for about a year, and were often seen together in Los Angeles and New York City. They split in 2015, but remained on friendly terms.

Tess Ward


Harry Styles
LONDON, ENGLAND – FEBRUARY 13: Tess Ward attends a Valentine’s dinner at The Living Room Champagne and Cocktail Bar by Perrier-Jouet at Restaurant Ours on February 13, 2018 in London, England. (Photo by David M. Benett/Dave Benett/Getty Images for Perrier-Jouet)

In 2017, Styles began dating Tess Ward, the British chef and food blogger. The couple were together for about a year, and were often seen together at restaurants and cafes in London. They split in that year, but remained on friendly terms.

Camille Rowe


Harry Styles
PARIS, FRANCE – MARCH 08: Camille Rowe attends the Miu Miu Womenswear Fall/Winter 2022/2023 show as part of Paris Fashion Week on March 08, 2022 in Paris, France. (Photo by Jacopo Raule/Getty Images)

In 2017, Styles began dating French-American Victoria’s Secret model Camille Rowe. The couple were often seen together at public events and parties, and Rowe was even included in Styles’ song “Cherry.”

Olivia Wilde


Harry Styles
VENICE, CALIFORNIA – DECEMBER 08: Olivia Wilde attends Audi and Olivia Wilde’s Sustainable Dinner Celebration on December 08, 2021 in Venice, California. (Photo by Stefanie Keenan/Getty Images)

In 2020, Styles began dating Olivia Wilde, the American actress and director. The couple met on the set of the film Don’t Worry Darling, which Wilde was directing and Styles was starring in. They were first seen together in January 2021, and were inseparable ever since.

Styles and Wilde’s relationship has been the subject of much media attention, being photographed together on numerous occasions and seen packing on the PDA. The pair ultimately called it quits in late 2022 due to their differing busy schedules.