Harry Styles' search for 'stability' in age-gap relationships explained

From Caroline Flack and Kendall Jenner to Taylor Swift, the Grammy winner has dated a galaxy of stars. Here, we unpack why he gravitates towards women who were considerably older than him...

Harry Styles performs on stage, singing into a microphone while wearing a sparkly purple bodysuit

2 minutes agoFeb 2, 2026, 9:00 PM GMT

Stability amid the storm

A 17-year-old Harry Styles smiles while wearing a grey "Harry Heart Louis" T-shirt. — Harry was 17 when he started dating Caroline

Our story begins in 2011, when Harry was competing on The X Factor with his band members to try and win over both voters and his future boss, Simon Cowell. That's where he met Caroline Flack, who was hosting the after-show, The Xtra Factor. The two began seeing each other, despite Harry being 17 years old at the time, and Caroline being 32.

"I already knew that he had a crush on me, he'd made it pretty obvious," she wrote in her 2015 autobiography, Storm in a C Cup. Shelly explained that the turmoil of Harry's life at the time, what with starring on a show watched by millions before he could even legally drink, might've nudged him towards Caroline, who provided a sense of stability.

"Younger men may be drawn to the self-assurance and emotional regulation that older women often display. This can be linked to attachment theory; if someone has grown up with uncertainty or instability, the calm presence of a more experienced partner can feel especially attractive."

Caroline Flack wears a white lace dress with quarter-length sleeves. — Caroline received online abuse for dating the singer

Fans quickly got wind of their romance, and Caroline endured relentless online bullying. It put a strain on the relationship, and the pair split after a few months. "We were both single, we got on well and we had a laugh. It was only when it became public knowledge that things turned sour," she wrote in her book.

"At the beginning, it was all very playful. He joked about being attracted to older women. It began to go wrong when Harry was pictured coming out of my house one morning. And once that was out, it was open season. After that, anyone could say anything. In the street, people started shouting at me, 'paedophile' and 'pervert.'"

Caroline tragically died in 2020, and despite the pair breaking things off eight years earlier, Harry paid a quiet tribute to her by wearing a black ribbon to the Brit Awards that year.

Confidence is key

Harry Styles and Olivia Wilde walk hand-in-hand while both wearing sunglasses — Harry dated Olivia for almost two years

One of Harry's longest relationships was with actress and director Olivia Wilde, whom he dated for almost two years between 2020 and 2022. The pair met when he was cast as the male lead in her film, Don't Worry Darling, and sparks flew between them despite their 10-year age gap.

Despite the 'Watermelon Sugar' crooner being a relative newcomer to the acting world, Olivia couldn't help but sing his praises in February 2021 on Instagram: ''Little-known fact: most male actors don't want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e., financial value) to accept these roles. Enter: @harrystyles, our 'Jack'…he infused every scene with a nuanced sense of humanity.''

She continued: ''He didn’t have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards.'' In short, she was already swooning over this man (and who amongst us wouldn't?).

Olivia Wilde wears a vibrant yellow dress and glances over at Harry Styles, who is dressed in a blue suit. Between them, Sydney Chandler wears a black off-the-shoulder dress — He was the lead in her film Don't Worry Darling

Susie explained that Olivia's self-assurance may have been a key draw: "There is something equitable about partners having independent careers and financial independence – it takes so much pressure off of a relationship, particularly in the long term. The attraction of being with someone older is predicated on intangible values such as confidence, experience and independence."

Similarly, Shelly shared that their romance possibly allowed Harry to "explore identity without the burden of being the provider," which is seen "as a way of borrowing stability from a partner at a different life stage".

Shaped by women

Harry Styles wears a North Face jacket and sunglasses as he puts his arm around his mother, Anne Twist. Anne is smiling and wears a black fluffy velvet coat, sunglasses and a white hat. — Harry shares a tight bond with his mother, Anne Twist

Harry's family background may also shed light on his dating choices. According to Susie, the concept of transference in Psychodynamic theory could explain why some men are attracted to older women, in that they are seeking a "replacement caregiver". Harry grew up in a female-centred household alongside his older sister Gemma after his mother, Anne Twist, divorced his father, Des Styles, when Harry was seven.

Anne herself once pointed out that she had a 10-year-age gap with Des, and noted that this could have influenced her son. "I never really thought about the age gap, but I had an age gap with Harry's dad so I suppose that's what he saw. I don’t think it's very important, to be honest," she told Heat magazine.

Interestingly, Anne's age was her son's yardstick for dating older women once upon a time. When asked if he liked mature women, the then-18-year-old Harry replied: "Anything up to my mum's age!" In case you're wondering, she was 44 at the time, which is quite the gap!

Harry Styles (L) wears a suit with his arm around his sister, Gemma Styles, who is dressed in a black and white patterned dress with tights. — The Grammy winner is also close with his older sister, Gemma

The closest he ever got to dating anyone near his mother's age, aside from Caroline, was Kimberly Stewart, Rod Stewart's actress daughter (to be fair, she was only 33!). Kimberly was 14 years older than him when they shared a brief fling in early 2013, with paparazzi spotting them on a dinner date together.

It was Rod who eventually spilt the beans about their dalliance – because it always seems to be the father that can't keep a secret – revealing on Alan Carr: Chatty Man that he had met the 'What Makes You Beautiful' singer.

"[Harry's] car was here in the morning. Let's put it that way," he teased. "But he may just have come round to pick something up...[expletive], I've let the cat out of the bag. Harry couldn't be kinder. He is a very funny guy."

Closer to home

Camille Rowe wears a black top and matching skirt paired with heels — The British native dated French model Camille Rowe for a year

While Harry's romances with the aforementioned stars are well-documented, the Cheshire native also dated several women who were closer in age to him, and one who was even five months younger (gasp!).

He was briefly linked to Cara Delevingne and Kendall Jenner (who was younger), as well as a slew of other models. One of his longest relationships was with French model Camille Rowe, whom he dated for a year between 2017 and 2018. It reportedly got so serious that he introduced her to his parents, and even wrote the song 'Cherry' about her (that’s Camille's voicemail you can hear at the end of the track).

She was just four years his senior. In the same vein, he shared a year-long romance with actress Taylor Russell – who is around five months younger than him – from June 2023 to May 2024.

Taylor Swift wears a burgundy coat, a woolly yellow scarf, and jeans as she walks alongside Harry Styles. Harry is dressed in a coat, jeans, and a hat. — Harry and Taylor were together for two months

Perhaps one of his most public relationships was with Taylor Swift in 2012, which, though fleeting, left a lasting impact on pop culture (and Swifties worldwide). After all, we did get the legendary 1989 album out of it, with hits like 'Style' and 'Out of the Woods' documenting their fling. Harry was 18 at the time, while Taylor was 22, and the duo were spotted on sweet dates in New York several times. They split after just a few months of dating, yet their legacy lives on in song.

His most recent partner, Zoë Kravitz, is only five years older than him, and the couple appear to be enjoying each other's company if their strolls through Brooklyn, London and Rome are anything to go by – talk about international love!

Zoë Kravitz wears a black dress, posing with her hair down. — Harry has been linked to Big Little Lies actress Zoë Kravitz

According to Shelly, the longevity of such relationships depends less on the age gap and more on having shared values in life. Similarly, Susie explained that these relationships may break down not as a result of incompatibility but from external pressure.

"There is a tendency to think of age imbalance relationships as temporary, and research shows that there is a higher separation rate in this relationship category…it could be that societal pressure plays a part," she explained.

Susie pointed out that there were many instances in Hollywood of successful age gap relationships, especially when it came to the LGBTQIA+ community. "Interestingly, in same sex relationships, the statistics [of longevity] are much higher…Sarah Paulson and Ellen DeGeneres are in long-term relationships where there are 32-year and 15-year age gaps, respectively."

Under the spotlight

Harry Styles performs on stage in a sparkly red jacket while holding a microphone. — Harry has almost exclusively dated famous women

An intriguing element of Harry's dating history is that most, if not all, of his past loves were famous in their own right. Susie suggested this may not be a coincidence. "Being constantly publicly scrutinised is not for the faint-hearted. And though there may be factors that could make older women – particularly older women who are also in the public eye – more adept at dealing with this, it all depends on the individual personalities."

Shelly echoed this point, explaining: "Fame can distort dating pools by making peers either unavailable or overwhelmed by the spotlight. Older women who are already successful and established may offer a safer base, echoing what psychologists call a secure base in attachment theory."

Harry Styles poses for the camera wearing a black shirt — He may gravitate to older women due to their self-assurance and confidence

All in all, Harry seems to be attracted not just to older women, but to those who radiate confidence, self-assurance, and success. Whether it was Taylor Swift, Olivia Wilde, or even Cara Delevingne, he has always been drawn to women who know exactly who they are and aren't afraid to showcase their individuality in an industry that craves conformity.

And who could blame him? While society often looks unfavourably on these kinds of romances, it’s clear that Harry doesn't care – he will always unapologetically follow his heart.