Harry Styles Dating History From Taylor Swift to Zoe Kravitz – Why He Keeps Falling for Older Women
Harry Styles is one of the most talked-about musicians in the world, not just for his music but also for his magnetic personality, gender-fluid fashion, and romantic relationships. From his teenage days in The X Factor to becoming a global superstar with One Direction and later as a solo artist, Harry has been in the spotlight for nearly 15 years. Along with his professional milestones, his dating history has been a subject of massive curiosity for fans and media alike. Harry Styles Dating History
Interestingly, one recurring pattern in Harry’s relationships is that many of the women he has dated have been older than him. Whether it was TV presenter Caroline Flack, pop superstar Taylor Swift, actress Olivia Wilde, or his latest rumored flame Zoe Kravitz, Styles has often found himself drawn to women with more experience, maturity, and established careers.
In this in-depth post, we’ll take you through Harry Styles’ complete dating history, from his pre-fame romance to his most high-profile relationships, rumored affairs, and his current love life.
Early Life and Rise to Fame
Before diving into his love life, it’s important to understand the trajectory of Harry’s fame. Born on February 1, 1994, in Redditch, Worcestershire, England, Harry Edward Styles grew up in Holmes Chapel, Cheshire. At 16, he auditioned as a solo contestant on The X Factor UK in 2010. While he didn’t make it through as a solo artist, Simon Cowell grouped him with four other contestants—Niall Horan, Louis Tomlinson, Liam Payne, and Zayn Malik—forming One Direction. Harry Styles Dating History
The band became a worldwide phenomenon, selling out stadiums and breaking records. But in 2016, the group went on hiatus, and Harry embarked on his solo career, debuting with Sign of the Times in 2017. With multiple Grammys, BRIT Awards, and chart-topping hits like Watermelon Sugar and As It Was, Styles has established himself as a generational superstar.
However, fame also meant that his relationships, casual flings, and even rumored romances became global headlines.
Harry Styles’ First Known Relationship – Felicity Skinner
Before fame, Harry dated Felicity Skinner, a girl from his hometown. They reportedly met through mutual friends when Harry was just 15. According to Felicity, Harry was always “romantic, shy, and a really good boyfriend.” Harry Styles Dating History
Their teenage love didn’t last long, and they eventually broke up before Harry’s big break on The X Factor. Even though it was a short-lived romance, it highlighted Harry’s sweet, caring nature, which many of his future partners have spoken about.
Caroline Flack – The Controversial Love Story (2011-2012)
Harry’s first major public relationship was with Caroline Flack, the beloved TV presenter best known for Love Island. They met in 2011 while Harry was just 17, and Caroline was 32—making headlines due to their 15-year age gap. Harry Styles Dating History
Caroline later revealed in her memoir that Harry made his interest in her very clear. Despite the criticism, they genuinely enjoyed their time together. Unfortunately, the intense media scrutiny and the glaring age difference became too much, and the relationship ended in 2012.
Tragically, Caroline Flack passed away in 2020. During the BRIT Awards that year, Harry paid tribute by wearing a black ribbon on his suit.
Emily Atack and Emma Ostilly – Short Romances
After Caroline, Harry was briefly linked to Emily Atack, the British actress from The Inbetweeners, in 2012. Emily later described it as “just a bit of fun,” and the two moved on quickly.
Around the same time, Harry also dated model Emma Ostilly, who appeared in One Direction’s Gotta Be You music video. They were spotted kissing in New Zealand, but the relationship didn’t progress further. Harry Styles Dating History
Taylor Swift – The Most Iconic Romance (2012-2013)
Perhaps Harry’s most famous relationship was with Taylor Swift, one of the biggest pop stars in the world. The two dated in late 2012, when Harry was 18 and Taylor was 23. They were seen together in New York, celebrated New Year’s Eve with a kiss in Times Square, and even vacationed together. Harry Styles Dating History
However, their romance was short-lived, ending in early 2013. Reports suggest a snowmobile accident during a ski trip in Utah left Harry with a scar on his chin, adding drama to their love story.
The breakup inspired some of Taylor’s biggest hits, including Style and Out of the Woods, while Harry later admitted the relationship was a valuable learning experience. Interestingly, years later, the two have been seen warmly interacting at award shows, proving they’re on good terms. Harry Styles Dating History
Kimberly Stewart and Nicole Scherzinger – Older Women Again
After Taylor, Harry was linked to Kimberly Stewart, daughter of rock legend Rod Stewart. Kimberly was 33, while Harry was just 19. They were spotted having dinner with Rod and his wife, sparking speculation of romance.
Around the same time, Harry also briefly dated Nicole Scherzinger, who was 35 then. Though never confirmed, the fling reportedly happened when Harry was 19, once again reinforcing his pattern of dating older women.
Georgia Fowler and Tess Ward – Brief Encounters
Harry was later linked to New Zealand model Georgia Fowler, who fans believe inspired his hit Kiwi. Their short romance was documented on Snapchat, but it fizzled out quickly.
Soon after, he dated Tess Ward, a food blogger and author. The two enjoyed each other’s company but split within a few months, with Tess eventually getting back with her ex. Harry Styles Dating History
Kendall Jenner – The On-and-Off Romance
Harry’s relationship with Kendall Jenner was one of his most private yet widely speculated affairs. First linked in 2013, the two insisted they were just friends. However, in early 2014, they vacationed together, confirming their romance. Harry Styles Dating History
After breaking up, Harry and Kendall rekindled their relationship in 2015, even being spotted on a yacht together. They dated until 2016 before parting ways. Despite the breakup, they remain close friends and have been seen supporting each other over the years.
Camille Rowe – The Serious Relationship (2017-2018)
In 2017, Harry began dating Camille Rowe, a French-American model. This was one of his longest and most serious relationships. He was reportedly very invested in her, and their romance inspired multiple songs on his 2019 album Fine Line.
In fact, Camille’s voicemail can be heard in his song Cherry. However, after nearly a year together, the couple split amicably in 2018. Harry Styles Dating History
Olivia Wilde – A Two-Year Relationship (2021-2022)
Harry’s romance with actress-director Olivia Wilde was one of his most talked-about relationships. The pair met on the set of Don’t Worry Darling, which Olivia directed. Their relationship went public in early 2021 when they were photographed holding hands at a wedding. Harry Styles Dating History
The 10-year age gap between them fueled headlines, and the relationship faced scrutiny, especially since Olivia had recently split from fiancé Jason Sudeikis. Despite the criticism, Harry and Olivia dated for nearly two years before breaking up in late 2022.
Reports suggest the breakup was due to busy schedules—Harry was touring, while Olivia focused on her children and career.
Taylor Russell – The Actress Girlfriend (2023-2024)
In 2023, Harry was linked to Canadian actress Taylor Russell. The couple was spotted together multiple times, and Taylor even attended his concerts. Their relationship seemed serious, but by mid-2024, they reportedly broke up after a tense trip to Japan. Harry Styles Dating History
Zoe Kravitz – The Latest Rumored Love Interest
In 2025, Harry has been rumored to be dating actress and singer Zoe Kravitz, known for her role as Catwoman in The Batman. Zoe, who is six years older than Harry, has been seen walking hand in hand with him in Rome, sparking romance rumors.
While neither has confirmed the relationship, fans are excited to see where this rumored pairing heads. If true, it once again highlights Harry’s attraction toward confident, older women with strong personalities. Harry Styles Dating History
Why Does Harry Styles Date Older Women?
One of the most fascinating aspects of Harry Styles’ dating history is his repeated attraction to older women. While only Harry knows the real answer, fans and relationship experts speculate that: Harry Styles Dating History
- Maturity: Older partners may bring more stability and emotional maturity.
- Confidence: Many of Harry’s partners are strong, independent women.
- Shared Interests: Being in the entertainment industry, he likely connects with women who understand the pressures of fame.
Conclusion
Harry Styles’ dating history is a fascinating journey through young love, high-profile romances, casual flings, and rumored relationships. From Taylor Swift and Kendall Jenner to Olivia Wilde and Zoe Kravitz, Harry has been linked to some of the most famous women in the world. Harry Styles Dating History
What’s clear is that Harry has always approached relationships with respect and kindness. Even after breakups, many of his exes have spoken positively about him. As of 2025, fans eagerly await confirmation of his rumored relationship with Zoe Kravitz.
One thing is certain—whether it’s his music, fashion, or love life, Harry Styles will always keep the world intrigued.