Harry Styles' Dating History: From Taylor Swift To Romance With Zoe, Keeps Falling For Older Women

Harry Styles rose to fame at the young age of 16. His audition as a solo artist for The X Factor in 2010 changed his life forever. He was paired with four other contestants in a group that later became One Direction. The band grew to become the biggest boy band after The Beatles. However, in 2016, they parted ways, and Harry finally pursued his solo career, breaking norms and stereotypes that had been formed about and around him over the years. 

However, growing up in the industry has kept most of Harry Styles' life in the spotlight, which also includes his romantic affairs in the past two decades. The Watermelon Sugar singer has dated several gorgeous women. It is also interesting to note that most of these women have been older than Harry. So, without any further ado, let us take a look at Harry Styles' star-studded dating history.

Harry Styles' pre-fame romance with Felicity Skinner

Ever since Harry Styles rose to fame in 2016, his female admirers have often called him a 'man written by a woman'. He is gentle, considerate, chivalrous and respectful. However, it's not something he adapted post-fame, according to his pre-X Factor girlfriend, Felicity Skinner, Harry had always been 'a really good boyfriend, very romantic and shy'.

They met through mutual friends at the age of 15. However, they soon parted ways, and while the reason for their breakup is unknown, many believe it was a baby-love that they grew out of.

Harry Styles and Caroline Flack's love couldn't stand the 15-year age gap

Harry Styles' first very publicised relationship happened when he was only 17 years old in 2011. The singer met Caroline Flack on The X Factor and soon started dating. However, while Harry was 17 at the time, Caroline was 32 years old, which garnered a lot of public scrutiny. The TV presenter, in her memoir, revealed that Harry had made his interest in her extremely clear.

However, they could not navigate the massive age gap and eventually parted ways. Almost 8 years later, Caroline committed suicide at the age of 40. While Harry didn't attend her funeral, as she had a private service, he wore a black ribbon on his lapel during the 2020 Brit Awards as a tribute to her. 

Harry Styles' short romances with Emily Atack and Emma Ostilly

In 2014, Harry Styles was linked to the Inbetweeners star, Emily Atack. The actress confirmed having 'just a bit of fun' with the One Direction member. However, both of them moved on rather quickly. It is also interesting to note that Emily was five years older than Harry. Before Emily, Harry was linked to model, Emma Ostilly, who is a year older than the singer.

Emma also appeared in the boy band's music video for Gotta Be You. They were spotted kissing in New Zealand in 2012. However, it seems like that didn't last long, as soon after, Harry was in a relationship which was soon labelled as the most high-profile relationship in his career.

Harry Styles and Taylor Swift's romance ended in some historic songs and 20 stitches in a hospital room

Arguably, Harry Styles' most high-profile relationship happened in 2012, with the pop icon, Taylor Swift. The duo had an age difference of five years as Taylor was 23, while Harry was only 18. They were photographed together in New York and shared a New Year’s Eve kiss in Times Square. 

Their breakup in early January 2013 inspired several of Taylor's songs in her album, 1989, including Style, Out of the Woods, Is It Over Now? and Now That We Don't Talk. Harry later shared that the relationship was a learning experience, and he had no issue with her writing about it. According to reports, the duo was involved in a snowmobile accident during a ski trip in Park City, Utah.

The crash occurred when Styles, who was riding with Swift, hit the brakes too soon, resulting in a scar on his chin from the impact. The two now share a good bond, as proved again and again with their interaction during award shows.

Harry Styles' series of short-lived romances

After Taylor Swift, Harry Styles was linked to Rod Stewart's daughter, Kimberly. She was 33 at the time, and Harry was 19. They were spotted on several instances, including a dinner with Rod and his wife. However, their relationship ended soon after, and Harry started seeing Nicole Scherzinger. As It Was singer and X Factor judge's casual fling lasted a short while, as she was 35 at the time and Harry was only 19. 

Harry Styles then dated Georgia Fowler, who was two years older than him. However, their Snapchat documented love was short-lived. According to fans, Harry wrote Kiwi about her, but the model has denied it. He then briefly dated food blogger and author, Tess Ward, who was four years older than him, but they broke up soon after, and she got back with her ex.

Harry Styles' two-part romance with Kendall Jenner

Harry Styles first sparked dating buzz with Kendall Jenner in 2013. However, both denied the speculations, maintaining that they were only friends. Nonetheless, their vacation together in early 2014 suggested otherwise. They broke up soon after, but then reunited again in 2015 and dated until mid-2016, before parting ways for good. Harry's relationship with Kendall was one of the most private affairs he had, since entering the industry.

Harry Styles was serious about his relationship with Camille Rowe

In 2017, Harry Styles found love in the arms of Camille Rowe. The two had a serious relationship, with Harry even including a voicemail from her in his song, Cherry. However, they broke up after about a year but reportedly remained on good terms.

Harry Styles' romance with Olivia Wilde

Harry Styles and Olivia Wilde's relationship was one of the least popular among fans. With a decade between them, the duo met on the set of Don't Worry Darling, and Olivia had recently ended her engagement with Jason Sudeikis. Their relationship drew major media attention and lasted nearly two years. They amicably split in late 2022 as Harry began touring and Wilde focused on her children.

Harry Styles' romance with Taylor Russell

Harry and Taylor were first spotted together in 2023. The Canadian actress accompanied him to several concerts. By late 2023, the duo was serious about each other. However, in May 2024, their breakup was confirmed following reported tension after a trip to Japan.

Harry Styles' rumoured relationship with Zoe Kravitz

Harry is now allegedly seeing Zoe Kravitz, who is six years older than the Fine Line singer. The buzz gained traction after the duo was seen walking hand in hand on the streets of Rome. However, while the buzz is not confirmed, fans are excited to see how things will go down between the 'Catwoman' and the 'Golden' boy.

What are your thoughts on Harry Styles' dating history? Let us know.

Next Read: Kokilaben Ambani Broke The Feud Between Her Sons, Mukesh And Anil Over The Family Business Empire

AWESOME NEWS! Now you can download BollywoodShaadis app and never miss a story. Get App

AWESOME NEWS! Now you can download BollywoodShaadis app and never miss a story. Choose your device Android or IOS (Apple)