After a devastating relationship breakup, I threw myself into the dating scene by registering on Hily. I had over 100 dates - some absolute disasters, some pretty average, and some that were actually great. So many stories to tell and insights to share with you guys!
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Is Harry Styles Dating Anyone?
Harry Styles isn’t officially dating anyone at the moment. He is being private about his dating life, and for a good reason. But that hasn’t kept fans from speculating.
Few modern-day celebrities command as much attention as Styles. From his early days with One Direction to solo pop star to Hollywood leading man, devoted fans have followed Harry’s every move—especially his love life.
Taylor Swift. Olivia Wilde. Kendall Jenner. Taylor Russell! Nothing gets fans going like celebrity couples. Below, we take a look at Harry’s long and winding dating path–from his confirmed romances to the intriguing rumors.
Who Is Harry Styles Dating Right Now?
Officially, Harry Styles is not dating anyone right now. But that’s not terribly surprising. After his high-profile, high-drama relationship with Olivia Wilde ended in 2022, the singer has remained relatively private about his personal life. Most recently, he was linked to actress Taylor Russell. (More on that later!)
Styles hasn’t publicly revealed that he’s dating anyone, but that doesn’t necessarily mean he’s single. Who could blame him for wanting to keep his romances under wraps?
Most recently fans have speculated about his potential connection with Taylor Russell, an actress best known for her role in Bones and All. The pair were spotted together several times throughout 2023, including at Taylor’s play in London and other public events. However, neither has confirmed any romantic involvement, leaving their status up in the air.
But for now, Harry seems to be focusing on his career and personal growth. If he’s dating anyone, he’s not in any hurry to discuss it with the public.
Related reading: How to Glow Up and Be Your Best Self: A Step-by-Step Guide
A Look at Harry Styles’ Dating History
Styles’ dating life is a mix of confirmed relationships and rumored romances. All of the relationships have drawn plenty of attention, both to Harry and the other party. As for opinions on the pairings? There’s no shortage of those, and sometimes, things can get pretty intense!
Caroline Flack (2011)
Harry’s first widely publicized relationship was with TV presenter Caroline Flack in 2011. The romance began when Harry was just 17 years old and Caroline was 31, sparking media attention due to their 14-year age difference. It might have been the first but it wouldn’t be the last big age gap for Harry!
The two met on the set of The Xtra Factor. Caroline later revealed in her autobiography, Storm in a C Cup, that Styles initiated the relationship. Despite their connection, the backlash was swift, with fans accusing Caroline of taking advantage of Harry. There was even a hate campaign complete with voodoo dolls!
The relationship ended after a few months, with both parties citing intense public scrutiny as the main factor. Harry has never spoken ill of Caroline and even attended her funeral in 2020 after her tragic passing, showing respect and care despite their relationship being brief.
Taylor Swift (2012–2013)
How many celebrity pairings have generated as much buzz as Harry Styles and Taylor Swift? The pop phenoms were first linked in late 2012, when they were spotted on a series of cozy dates in New York City. There was even a famous Harry-and-Taylor walk through Central Park that fans still talk about to this day. The Big Apple plus the biggest stars on the planet? It was a recipe for love!
The whirlwind romance lasted only a few months but left an indelible mark on both stars’ music careers. Taylor is believed to have written several songs about Harry, including “Style,” “Out of the Woods,” and “I Knew You Were Trouble.” Let’s call that: Taylor’s version.
As for Styles, fans speculate that “Two Ghosts” reflects on his time with Taylor. But despite the media frenzy surrounding their breakup, Harry has always spoken respectfully of Taylor. They seemed like a lovely couple, but whether it was their busy schedules, their massive fame, or all that stuff combined, their union simply wasn’t built to last.
Kendall Jenner (2013–2016)
Harry and Kendall Jenner’s on-again, off-again relationship has been the subject of speculation since 2013. Over the years, they’ve been photographed vacationing on yachts, attending fashion week, and sharing flirtatious moments on talk shows.
In 2019 Harry and Kendall appeared on The Late Late Show with James Corden and participated in a segment called “Spill Your Guts or Fill Your Guts.” Their playful banter and obvious chemistry sparked rumors that there was still a love connection between the two.
Even after their romantic ties faded, Kendall has continued to attend Styles’ concerts and support his career. They seem to be avoiding all the drama by making a very amicable decision to keep things friendly. Either way, it’s pretty obvious the two care for and appreciate one another.
Related reading: Kendall Jenner and Bad Bunny: A Match Made in Heaven
Camille Rowe (2017–2018)
The singer started dating model Camille Rowe in mid-2017. Camille, known for her effortless Parisian style and work with brands like Victoria’s Secret, seemed to be a grounding influence on Harry.
Their breakup in 2018 had a profound impact on Harry, and it seemed to inspire a good deal of material on his album Fine Line. Attentive fans have drawn connections between Camille and several songs, including “Cherry,” which features a voicemail from Camille in French, and “Falling.”
Olivia Wilde (2021–2022)
“I think we are going to see more and more age-gap relationships because of a greater sense of acceptability of different relationship sizes and shapes.”
Galena Rhoades, research professor and psychologist
Harry and Olivia’s relationship dominated headlines. The pair met on the set of Don’t Worry Darling, where Olivia directed Harry in his first major role. Sparks flew early on, with their relationship becoming public in January 2021.
Their romance was marked by intense scrutiny, partly because of their 10-year age difference. Olivia was also married with two kids when she met Harry—to Ted Lasso star Jason Sudeikis. But the couple seemed invested. In 2022, the singer performed a 15-night residency at Madison Square Garden in New York City, and Olivia was seen supporting him. The two also turned heads at the Venice Film Festival during the premiere of Don’t Worry Darling, sparking just a bit more buzz.
In November 2022, reports emerged that Harry and Olivia had amicably ended things. Insiders cited scheduling conflicts and the pressures of public attention, but neither has commented publicly. As for Olivia, she seems to be focusing on her kids and career at the moment. She is now divorced from Sudeikis and they share custody of their two children.
Harry Styles and Taylor Russell: Very Close Friends or More?
One of Harry Styles’ most recent romantic rumors involved dating Taylor Russell. Known for her breakout roles in Waves and Bones and All, Canadian actress Taylor Russell captivated fans with her acting chops and her rumored connection to Harry. The speculation began in mid-2023 when the pair were spotted at public events, including Harry’s Love On Tour concerts and Taylor’s stage performance at the National Theater.
Suspected girlfriend Taylor Russell appeared at Harry’s Vienna concert during the summer of 2023, where she was spotted in the VIP section with his friends and family.
Another key moment was the now-iconic “obvious Taylor” interaction. During a concert, Harry introduced his band, and when he came to Sarah Jones, his drummer, he remarked, “On the drums, it’s the obvious Taylor.” Fans immediately interpreted this as a cheeky reference to Taylor Russell. The comment sent social media into a frenzy, with hashtags like #ObviousTaylor trending for days.
Taylor Russell brought a sense of mystery to Harry’s dating history, especially because neither of them ever confirmed or denied the relationship. Despite the buzz, the relationship appeared to be short-lived or perhaps hit a rough patch, with reports fading by the end of 2023. I guess you could say they went in opposite directions!
Good Friends or Romantically Linked?
Whether they were brief celebrity couples, very good friends, learning experiences, or just peers he loves spending time with, the world may never know.
- Kimberly Stewart: At one point in 2013, Harry Styles was briefly linked to Kimberly Stewart, daughter of rock legend Rod Stewart. While their connection was never confirmed, reports at the time hinted at a short-lived fling.
- Olivia Dean: Although unrelated to his dating life, Harry Styles has also collaborated with talented artists like Olivia Dean, further showcasing his knack for supporting emerging talent. Naturally, anyone the former One Direction member is linked to is subject to scrutiny by watchful fans, which is probably a bit awkward.
- Georgia Fowler: New Zealand model Georgia Fowler was rumored to be dating Harry Styles in 2015 after a cozy Snapchat story fueled fan speculation.
- Emily Ratajkowski: In early 2023, Harry Styles was briefly linked to model Emily Ratajkowski after photos of them together emerged, though neither confirmed a romance. It’s possible they were just friends, just like many of the other high-profile women on this list.
- Tess Ward: In 2017, Harry Styles was briefly linked to chef and food blogger Tess Ward, whose focus on healthy and innovative recipes gained her a significant following. Fans speculated about their relationship when Tess was seen wearing a Gucci shirt identical to one Harry had been photographed in during a New York city press tour.
How Harry Styles’ Dating History Influences His Music
Harry Styles has always used his music as a canvas for his emotions and experiences, with his relationships often serving as inspiration. From heartfelt ballads to introspective lyrics, his romantic history is woven into the fabric of his discography. Much like Taylor Swift’s fans, Harry’s devoted followers are expert sleuths when it comes to dissecting his lyrics and their possible meanings.
In addition to his lyrics, Harry’s music videos often include subtle nods to his personal life. For example, fans have drawn parallels between the themes in “Adore You” and “Golden” and specific moments in his past relationships. These details keep fans engaged, turning every release into a treasure hunt for clues about his love life.
Why Is Harry Styles Single Now?
Following his split from Olivia Wilde, Harry Styles has taken a step back from public relationships. In interviews, he has spoken about the challenges of dating in the spotlight, hinting that he values privacy and personal growth. No one knows whether Harry is definitely single, but if he is loved up, he’s choosing to keep it to himself. At least for now.
Fans coined the term “Harry Happy” to describe the singer’s current state of confidence and contentment. With his thriving music career, ongoing tours, and ventures into acting, Harry appears focused on his passions and well-being, embodying a chapter of self-discovery and balance.
Lessons From Harry Styles’ Love Life
- Privacy Matters
Throughout his career, Harry has insisted on maintaining boundaries between his public persona and personal life. That’s easier said than done, but he continues to make it a priority. His approach reminds us to protect our private moments and our intimate relationships, especially when they’re still new. - Growth Through Heartbreak
Harry’s openness about love and loss resonates deeply with fans. Songs like “Falling” and “Fine Line” capture the complexity of heartbreak, showing how personal experiences can lead to growth and artistic evolution. - The Power of Authenticity
Harry’s authenticity—whether in his relationships, music, or fashion—has made him a role model for embracing individuality. His love life serves as an example of staying true to oneself even in the face of public scrutiny.
Related reading: Modern Dating—Buckle Up
Harry Styles: Single For Now
Harry Styles may not be dating anyone right now, but his love life remains a source of intrigue for fans worldwide. Whether drawing from past relationships to fuel his music or choosing to focus on self-discovery, Harry continues to captivate audiences as an artist and cultural icon.
As the heartthrob with an irresistible English accent continues to focus on his career, fans will undoubtedly keep an eye out for him, whether it’s at sold-out concerts in London, on the red carpet, or casually strolling through New York between projects. Stay tuned for more stories on Styles!
Related reading: Tom Holland and Zendaya: Power Couple Story
Shelly Standford
