Thrust into the spotlight at just 16 years old, Harry Styles became an instant teenage heart throb. 

With his curly locks and cheeky charm, he was every teenagers 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 an older woman 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 X Factor spin-off show The Xtra Factor after the presenter host admitted she knew the singer had a crush on her before she pursued a romance with him. 

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.'

'I've never felt I was much older than Harry. I still feel 18 and I probably act that way half the time'

'Although it was just a bit of fun we decided it was best to keep it to ourselves as we were both working for Simon Cowell,' she explained to The Sun on Sunday.

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.

'We were both single, we got on well and we had a laugh. It was only when it become public knowledge that things turned sour. At the beginning it was all very playful. He joked about being attracted to older women.'

'It began to go wrong when he was pictured coming out of my house one morning. And that was that.'

'In the street people started shouting 'paedophile' at me in the street and 'pervert'.'

Following his brief fling with Caroline, a year later Harry started dating none other than 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.

During a performance at the Grammy Museum, she introduced Out of the Woods by telling the audience about her anxiety-inducing relationship - although she didn't mention Styles by name.

'I'm going to play you a song that I wrote about a relationship that I was in that the number one feeling I felt in the whole relationship was anxiety,' she explained as she sat at her piano.

'Because it felt very fragile, it felt very tentative. And it always felt like, 'Okay, what's the next road block? What's the next thing that's gonna deter this? How long do we have before this turns into just an awful mess and we break up? Is it a month? Is it three days?''

Next, Harry was linked to Kendall Jenner, but once again the romance didn't last long and they soon called it quits. 

However the pair were spotted getting cosy on a yacht in St Barts early in 2016 after ringing in the new year together.

Photos showed the pair nuzzling into each other as they lay out on the sun deck surrounded by friends, who just passed by and didn't distract them from each other for a second.

Shortly afterwards, the pair went their separate ways once again, but they appear to have remained friends as Jenner has been spotted at Styles's concerts supporting her ex in recent years.

Harry went on to date a series of Victoria's Secrets models as he was rumoured to be romantically linked to Georgia Fowler and Sara Sampaio. 

Georgia first sparked romance rumours with the singer after posting a sweet photo on her Snapchat page of Harry playing Scrabble with her, while dressed in a hoodie.

Little is known about the couple's reported romance as they remained tight-lipped in public about their relationship, however Georgia did her best to shut down rumours one of the songs on Harry's debut solo album was about her.

After fans buzzed around the lyrics to the song 'Kiwi', she was asked on Australia's The Morning Show if the tune was about her.

The song features the curious lyric: 'I think she said 'I'm having your baby, it's none of your business'.'

Presenter Kylie Gillies asked: 'Harry Styles, on his album has a song called 'Kiwi', can you confirm or deny that it was named after you?'

'Ah, don't really know anything about it,' Georgia shook her head, after referring to Harry as a 'friend'. She quickly added: 'Definitely don't have a baby... that's what the song is all about.'

Later in 2015, Harry and Sara were spotted partying in Manhattan one evening, and pictured saying goodbye outside Sampaio's hotel.

However, The Sun reported at the time that the Portuguese model later returned to the hotel, and emerged again the next morning around 11am, wearing the same clothes as the night before.

'There was definitely chemistry there as they hugged and kissed each other when she left but everyone thinks something was up as she came back and they left so soon after each other the next morning,' a source told the newspaper.

'Sara left at 11am dressed exactly the same. Then Harry walked out at 11.15am and it looked like he'd been partying pretty hard.'

In 2017 Harry and food blogger Tess Ward reportedly shared a 'whirlwind romance' after Tess was spotted wearing what appeared to be Harry's shirt.

Despite keeping their romance under wraps, it appeared to be over before it had even begun as the pair soon decided to spend time apart.

A source told The Sun at the time: 'Harry and Tess haven't seen each other for a number of weeks.'

The insider added: 'Tess realised she still had feelings for her ex after splitting from him to date Harry and has apologised to him for her romance with the singer.

'She was in London this week and met her ex straight away — they've been inseparable since'.

Another Victoria's Secret model came next, and Harry dated Camille Rowe for a year between summer 2017 and 2018. 

Although the pair never publicly confirmed their romance, they were reported to have met through their mutual friend, Alexa Chung.

After their romance came to light, Harry and Camille were spotted on a string of sightings together, including a sushi date.

The French beauty also turned out to lend her support at a slew of his concerts, including one which she attended with her mother Anne Twist.

Following the couple's split, Harry hinted during a promotional tour for his album Fine Line that some of the tracks on the record had been inspired by the romance.

Some fans suggested one of the lines in the song Falling hinted that Styles had been unfaithful to Rowe, referring to the lyrics: 'I'm in my bed and you're not here. And there's no one to blame but the drink and my wandering hands.'

In another song, dubbed Cherry, Harry appeared to mock Camille's new love interest art collector Theo Niarchos, whose father Philip owns an extensive collection.

Harry's words on the song say: ''Don't you call him 'baby', we're not talking lately. Don't you call him what you used to call me', before adding: 'Does he take you walking round his parents' gallery?'

Perhaps his most high profile romance, Harry went on to date director Olivia Wilde from late 2020 until November 2022 after they bonded on the set of her movie Don't Worry Darling.

By January 2021, the couple were spotted out and about holding hands for the first time, as they dressed in all their finery to attend the wedding of Harry's agent in Montecito, California.

The pair continued to date and grew closer over the next two years, with the singer reportedly meeting Olivia's children, who she shares with her ex Jason Sudeikis, as the relationship became more serious.

But in November 2022, just a few months after Don't Worry Darling premiered in cinemas, the couple announced they were 'taking a break' from their relationship.

The pair reportedly have 'no bad blood between them' as a source insisted that they mutually ended the relationship. 

A source told People: 'He's still touring and is now going abroad. She is focusing on her kids and her work in L.A It's a very amicable decision.'

Later in March 2023, Harry sparked romance rumours with Emily Ratajkowski after the two were seen enjoying a passionate smooch in Tokyo.

The model was sure to fan the flames when she later revealed she had been secretly dating Harry for two months – and even said he might be 'the one'.

She told all in a podcast interview recorded on March 9, where she sweetly gushed about how 'great' he is.

Emily said: 'I just started dating someone that I think I like, so that is different. I was like, 'He's kind of great'. But if you had been talking to me four weeks ago, absolutely. I would be seeing someone and then suddenly the way he would walk would be like, ugh.

'What do I look for in a partner? I like someone that is very independent. I think, for me, that's very important because I do have a full life. I'm hoping that dating someone that has more of their own life will prevent the issues I had before'.

After his relationship with Emily fizzled out, he began dating Taylor Russell, with Harry reportedly feeling as though she was the one. 

The pair were spotted on a cosy night out in August 2023 when the couple secretly attended the press night of her play The Effect at the National Theatre.

Sources at the time said the Watermelon Sugar singer reportedly 'sees a future' with Taylor.

'Harry is head over heels for Taylor,' a source revealed to Us Weekly, ' and he loves spending as much time with her as he can'.

Harry was even said to be ready to start a family with the Canadian actress.

Speaking in March before their split, a source told the Daily Mail: 'Harry feels as if he has lived ten lifetimes already, but one thing is certain – his 30s will be nothing like his 20s.

'He has experienced all the fame anyone could ever want. He is now ready for the next chapter.

'He is in love with Taylor. He wants a family with her and this is the next phase of his life.'

However the pair later split in May 2024 with friends claiming the couple opted to end the relationship after spending time together in the Japan on their final trip away together.

After his split from Taylor, the singer sent tongues wagging after he was spotted on a burger date at Five Guys with Olivia Dean. 

However it was never confirmed that they were dating and the duo were said to be just getting to know each other as they share a lot in common. 

Then in 2025, Harry's love life hit headlines again when he was spotted snogging in the VIP area at Glastonbury. 

Partying into the early hours, he was seen getting very close to a mystery woman who was later revealed as producer Ella Kenny. 

A source told The Sun at the time: 'Harry and Ella had fun together at Glastonbury and shared a kiss on the dancefloor.

'They had a good time in the moment but it doesn't mean it will evolve into anything. They just got on and had a snog.'

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 the services while driving back down to London together. 

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?

'If you're like touring all the time and you're doing this all the time and all these things, there's no space to really choose.

'I think I had a real honest conversation with myself about, okay, in five years, what do I want my life to look like? And then how do I make changes to aim at that? I don't want to be the guy who's on his own but was like, oh, I really did it.

'I want to be fulfilled and I want to be in great relationships with people. I want to have great friendships with people. I want a family. I want these things. 

'It just allowed me to go like, okay, what do I have to do to create space to allow these things to happen? I can't just expect them to just happen to me.'

Harry went on to talk the importance of building a future with the 'right person' as he explained: 'They hold you accountable to the person that they know you want to be. 

'I think accepting flaws and stuff is like, yes, having understanding is wonderful, but you know that I want to be better than that.

'So when you challenge me on something. It's a gift to me, actually.'

Harry's new outlook on life was influenced by watching his friends tie the knot, which inspired his song American Girls.

He said: 'I think the song to me is like, it's actually quite a lonely song in a lot of ways. I watched my three closest friends get married.

'And actually seeing them trust in something and risk something to find something truly fulfilling, in a way that isn't as like shiny and on paper as exciting as like, you know, watching them get married. I was like, I'm single, so I'm having all the fun.

'And American Girls is actually about watching them get married and like, you know, there just is a magic when you find the right person that you want to be with.

'But I think watching them do that. It's like being truly vulnerable with someone, like sharing a life with someone like that.

'Having the time to stop and assess all of it and really look at my life from a bird's eye view and go, 'what do I actually want in my life?' Like, I have all these things around me all the time. It's hard to pull those things in without making space for them.' 

And it seems Harry has found the right person, after the and Zoe sparked engagement rumours, after the actress was seen flashing a new diamond ring last week.

'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. It is bezel set, which is popular these days.'

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.' The insider added she appreciates that the rock star 'supports her in a beautiful, kind way.'