Home EntertainmentHollywood Harry Styles’ ‘Wilde’ Dating Timeline – From Kendall Jenner To Taylor Swift, All The Women That The Watermelon Sugar Singer Dated

Harry Styles’ ‘Wilde’ Dating Timeline – From Kendall Jenner To Taylor Swift, All The Women That The Watermelon Sugar Singer Dated

Harry Styles

Harry Styles' 'Wilde' Dating Timeline - From Kendall Jenner To Taylor Swift, Take A Look
Harry Styles’ ‘Wilde’ Dating Timeline – From Kendall Jenner To Taylor Swift, Check Out Here

Harry Styles is in love again and unlike all his past relationships, the Watermelon Sugar singer is out and about in public and holding hands with none other than her new girlfriend, Olivia Wilde. Yes, she’s the director of Don’t Worry Darling and this came as a surprise to all his fans!

Ever since Harry is spotted holding hands with Olivia, he has been trending crazy on social media all over the world.

Harry Styles fans are going gaga over her new relationship with Olivia Wilde as this is the first time the Watermelon Sugar singer was seen holding hands in public. Isn’t that amazing? Our hearts are melting already. The young singer has dated celebrities like Kendall Jenner and Taylor Swift in the past and always been very private about it.

Let’s take a look at Styles’ ‘Wilde’ dating timeline:

Caroline Flack (2011)

Caroline Flack

Late Caroline Flack was in her 30’s when she started dating Harry Styles who was just 17 back in 2011. They met on the sets of ‘X Factor’ and the Golden singer confessed his liking towards her and soon they became the news of the Tinseltown.

Although, the couple didn’t last long and broke up for their age-gap. Back in February 2020, the actress committed suicide at her London home by hanging herself.

Emily Atack (2012)

Emily Atack

Harry has always been very private and shy about his personal life and their relationship never went public for obvious reasons.

Harry Styles dated Emily Atack in 2012 and they never accepted their relationship in public until two years later when during an interview with Reveal Magazine, the actress said, “We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions.”

Taylor Swift (2012-13)

Taylor Swift

Taylor and Harry dated for almost a year and their romance was short-lived. Although their fans were ecstatic on hearing their dating rumours and really wanted this to last but as they say, everything happens for a reason.

Not just that, Taylor Swift and the Golden singer also wrote songs about each other but never really spoke about us but fans had a way to link the dots, well!

Nicole Sherzinger (2013)

Nicole Sherzinger

Can you even blame Harry Styles for dating Nicole, I mean, really? Just look at her. I know it sounds bizarre but you can’t plan on falling for someone. Love has its own way!

The Watermelon singer was 19 and the hottie was 35 when they were together and a source close to The Sun back in 2015 revealed that, “…They hooked up over three years later when Harry had matured and was a member of the world’s biggest band.”

Kendall Jenner (2013-14)

Kendall Jenner

This relationship took the internet by storm. Fans all over the world were really happy for these two lovebirds and two were spotted on quite a few dates together.

It all seemed lovey-dovey at the beginning and things starting to get sour soon for the couple. Kendall Jenner and Harry Styles dated for a short period of time before breaking up and hooking up later in the years again.

Erin Foster (2014)

Erin Foster

Yet another short-lived romance for Styles. The rumours started surfacing back in 2014 when the Golden singer stepped out together with the beauty for a fun day at a pumpkin patch as reported by the Daily Mail.

Reportedly, the couple met through mutual friends.

Nadine Leopold (2014-15)

Nadine Leopold

Harry Styles has undoubtedly dated one of the most beautiful women in the world including Victoria’s Secret model, Nadine.

The two were spotted on a few dates together but soon parted ways in March 2015.

Sara Sampaio (2015)

Sara Sampaio

Shortly after, the Golden singer broke up with Leopold, he started dating another Victoria’s Secret model, Sara Sampaio.

What even, Styles? After all, his charms work better than anything else in this world, I feel. Is there anyone, who this angel can’t impress with his kindness, Nah!

Georgia Fowler (2015)

Georgia Fowler

Okay, what is this behaviour Harry Styles? Haha, kidding. Yet another short-lived romance with Victoria’s Secret model.

Georgia confirmed their relationship by sharing a video of two playing scrabble together on her social media.

Kendall Jenner…Again (2015-16)

Kendall Jenner

Not your fault Harry. Old love has a habit of coming back, they say. Haha!

On a serious note, all the fans of the Golden singer really wanted this relationship to work. Again after a year of dating, the couple broke-up and it did break the hearts of fans. Tough luck, friends!

Tess Ward (2017)

Tess Ward

Finally, Harry Styles decided to take a break from dating models and started dating food-blogger, Tess Ward.

They kept their romance private until she left the singer to reconcile things with her ex.

Camille Rowe (2017-18)

Camille Rowe

Are they still bad habits, if we like them? Nah. After breaking up with Ward, Styles started dating yet another model and this time, Camille Rowe.

The couple dated for almost a year before parting their ways for good.

Kiko Mizuhara (2019)

Kiko Mizuhara

Reportedly, Harry Styles was dating Kiko for a very short period of time but the two never accepted their relationship in public. In fact, the model denied even knowing the singer.

It was when she was spotted at the Golden singer’s 25th birthday party and all the speculations came to an end.

Olivia Wilde (2021)

Olivia Wilde

Everything is well that ends well. Isn’t it? Yesterday, Harry Styles was spotted holding hands with her director friend Olivia Wilde and it’s driving his fans crazy.

Ever since the couple was spotted together, his fans are going gaga over his new budding relationship and trending him on social media.

The two met on the sets of ‘Don’t Worry Darling’ which happens to be Harry’s upcoming film directed by Wilde and also stars Florence Pugh and Chris Pine.

Which of the above-mentioned romances of Harry Styles were you rooting for? Tell us in the comments below.

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