Thrust into the spotlight at just 16 years old, Harry Styles became an instant teenage heartthrob. With his curly locks and cheeky charm, he was every teenager's fantasy crush, and it wasn't long before the One Direction star became known for his public relationships. From Caroline Flack to Taylor Swift and Olivia Wilde, it seemed clear that Harry had a preference for older women during his late teens and early twenties. However, the Aperture hitmaker, now 32, has ditched his wild ways and appears to be settling down with Zoe Kravitz, amid reports the pair are engaged after eight months of dating.
Ahead of the release of his recent record Kiss All The Time. Disco, Occasionally, Harry confessed he had to have a 'real, honest conversation' with himself as to where he saw himself in five years after watching three of his closest friends get married. Speaking to Zane Lowe on his Apple Music show, the star revealed he wants to get married and start a family as his relationship with Zoe continues to go from strength to strength.
Harry has had a colourful love life to say the least, and while he doesn't comment on it himself, he has been linked to numerous famous stars over the years. Rewinding back to his X Factor days, the star had a brief three-month romance with the late Caroline Flack in 2011, when he was 17 and she was 32. The pair met when Caroline was fronting the X Factor spin-off show The Xtra Factor. She said of their brief fling: 'I already knew that he had a crush on me, he's made it pretty obvious as he's said it in magazines.' Despite the age difference, Caroline explained that their relationship 'turned sour' when it went public, revealing that she suffered abuse from strangers in the street.
Following his brief fling with Caroline, a year later Harry started dating Taylor Swift, when she was 22 and he was 18. The couple dated from November 2012 but split just three months later in January 2013. Taylor, who is known to write songs about past relationships, is thought to have penned at least three songs about Harry: I Knew You Were Trouble, Style, and Out of The Woods. In 2015, the singer revealed her whirlwind romance with the One Direction star had been an experience filled with anxiety.
Next, Harry was linked to Kendall Jenner, but the romance didn't last long. However, the pair were spotted getting cosy on a yacht in St Barts early in 2016 after ringing in the new year together. Shortly afterwards, they went their separate ways once again, but they appear to have remained friends. Harry went on to date a series of Victoria's Secret models, rumoured to be romantically linked to Georgia Fowler and Sara Sampaio. Georgia first sparked romance rumours after posting a photo of Harry playing Scrabble with her, while Sara was spotted partying with him in Manhattan.
In 2017, Harry and food blogger Tess Ward reportedly shared a 'whirlwind romance', and he dated Victoria's Secret model Camille Rowe for a year between summer 2017 and 2018. Following their split, Harry hinted that some tracks on his album Fine Line were inspired by the romance. Perhaps his most high-profile romance was with director Olivia Wilde, whom he dated from late 2020 until November 2022 after they bonded on the set of her movie Don't Worry Darling. The pair announced they were 'taking a break' from their relationship, with a source insisting it was a mutual and amicable decision.
Later in March 2023, Harry sparked romance rumours with Emily Ratajkowski after they were seen enjoying a passionate smooch in Tokyo. The model later revealed she had been secretly dating Harry for two months and even said he might be 'the one'. After his relationship with Emily fizzled out, he began dating Taylor Russell, with Harry reportedly feeling as though she was the one. Sources said the Watermelon Sugar singer 'sees a future' with Taylor and was ready to start a family. However, the pair split in May 2024.
After his split from Taylor, Harry was spotted on a burger date with Olivia Dean, but it was never confirmed they were dating. Then in 2025, his love life hit headlines again when he was spotted snogging producer Ella Kenny at Glastonbury. Yet after his summer dalliances, Harry appears to have found love with Zoe Kravitz after they were first spotted holding hands last August. Keeping it low key, the pair spent Christmas together in Harry's home town and were later spotted at services while driving back down to London.
Ahead of the release of his latest album, Harry opened up about the 'loneliness' of fame and how he took a three-year hiatus from music to establish what he really wanted in life. He said: 'I stop everything, then I get to decide what I want to bring back in. Like what are really the things that I want in my life?' He went on to talk about the importance of building a future with the 'right person' and how watching his friends tie the knot influenced his song American Girls. Harry and Zoe have sparked engagement rumours after the actress was seen flashing a new diamond ring. 'Zoe's ring looks to be a ten-carat oval-shaped diamond set in yellow gold,' Chris from The Diamond Bank in Los Angeles told the Daily Mail. 'It was probably custom-made and costs around $1 million.' This sighting comes just as the Daily Mail has learned new details about the shock proposal. Zoe has told friends that she said yes right away to Harry's 'old-fashioned, romantic' proposal because she is 'madly in love with him.'
