Harry Styles’ love life – from model Kendall Jenner to pop star Taylor Swift

He might still be in his twenties, but Harry Styles has a very interesting dating history for someone his age.

The One Direction has enjoyed romances with a string of famous ladies and is reportedly now dating Hollywood actress Olivia Wilde.

It was claimed that Harry and Olivia, 36, had grown close on the set of their new movie Don't Worry Darling.

However, Olivia isn't the first older woman that Harry has dated and he's clearly a fan of a more mature lady.

From reality stars to TV presenters, the Worcestershire-born singer is certainly capable of charming the ladies. Here we take a look at his dating history…

Caroline Flack

Harry enjoyed a short fling with late television presenter Caroline Flack between November 2011 and January 2012.

Harry was just 17 at the time and their relationship stirred controversy as she was fourteen years his senior.

Sadly, Caroline passed away in February 2020 and just days after her death, Harry paid tribute to his ex when he walked the Brit Awards red carpet wearing a black ribbon on his suit jacket.

Taylor Swift

Harry briefly dated US singer-songwriter Taylor Swift later in 2012, leading to fan and media speculation about them writing songs about each other after their breakup.

The pair were pictured together a lot during their short romance, often holding hands and looking very loved-up.

Taylor's 2014 album entitled 1989 featured a lot of songs which referenced to their break-up, but Harry doesn't seem to mind.

During an interview with Howard Stern in 2020, Harry said: "I think about what it means to me to write a song about somebody else and for somebody else to do that, it’s like flattering.

"Even if the song isn’t that flattering, you still spent time on it and ultimately, using Taylor as an example, she’s a great songwriter. So at least they’re good songs."

Kendall Jenner

Harry enjoyed a romance with reality TV star and model Kendall Jenner which began in 2013 and ended some time in 2014.

The pair were spotted out and about together a fair few times, and even enjoyed a skiing trip as a couple.

They apparently rekindled it briefly in 2016 and were seen enjoying a date at Ysabel in Los Angeles.

In a 2017 interview with Rolling Stones, Harry admitted that his solo album at the time featured some songs inspired by Kendall.

Speaking to the magazine, he explained that the album is a tribute to his ex-girlfriend and described it as "tipping a hat to [their] time together".

And while he refused to give a name, he is believed to have been referring Kendall.

"Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it's just for them," Harry said.

Nadine Leopold

Harry clearly has a thing for models – more specifically, those who appear in Victoria's Secret Fashion Shows.

The dark-haired singer dated Austrian model Nadine Leopold, with the pair first sparking romance rumours when they were spotted together in November 2014.

Apparently set up through her agent Jeff Azoff, they went on to date for several months before calling it quits in early 2015.

Camille Rowe

From 2017 to 2018, Harry was in a relationship with French-American model Camille Rowe who inspired his 2019 album Fine Line.

Harry refers to their break-up on three songs specifically: Cherry, Falling, and To Be So Lonely, although the whole album has hints of Camille.

The former One Direction star suggests that he cheated on his ex in the opening lines of Falling.

Harry sings: "I’m in my bed and you’re not here, and there’s no one to blame but the drink and my wandering hands."

The heartbroken star continues: "Forget what I said, it’s not what I meant, now I can’t take it back."

Olivia Wilde

Harry is thought to be dating American beauty Olivia Wilde after he took over Shia LaBeouf’s role as Florence Pugh's love interest in Don’t Worry Darling.

According to MailOnline, the pair were spotted arriving back at his LA home with luggage after a trip to California in early January.

A source told the publication: "Olivia and Harry have become close and the pair have been spending a lot of time together in recent weeks.

"She has been seen visiting his home on several occasions."

Olivia recently told People that she "did a little dance" when the former X factor star agreed to star in her movie.

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