Harry Styles Hookup History: A Rundown Of The Singer’s Fiery Romances!

Ever since Harry Styles first entered the Hollywood scene, he has been a total heart breaker! So, it’s no surprise that his list of exes is super long and includes models, actresses, and more models.

And unlucky for all of us, he is off the market yet again! We apologize to Directioners as it’s not happening right now, so get over it!

Related: Mary-Kate Olsen: A Complete Dating History

In January, the Adore You singer practically confirmed his relationship with Olivia Wilde, who directed the leading man in her upcoming psychological thriller, Don’t Worry Darling. At the time, the now-couple was photographed together at his manager Jeffrey Azoff’s wedding in Montecito, California.

So in the spirit of celebrating a new romance, let us check out all of Harry’s exes (some confirmed, some not) from 2011 to now!

2011: Caroline Flack

After Harry gained fame with One Direction on The X-Factor, he briefly dated Caroline Flack. The former couple received a ton of push back at the time because of their 14-year-age gap. The two started dating when Harry was just 17, while the singing competition presenter was 31. In her autobiography, Storm in a C Cup, the Love Island UK host discussed the controversial relationship, writing:

“I still feel 18 and 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 continued, expressing:

“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 ‘pedophile’ and ‘pervert.’”

Once she started to receive death threats, though, the two decided to split. Unfortunately, the former actress died by suicide at the age of 40 back in February 2020. While at the Brit Awards in London, the singer seemingly honored his ex by wearing a black ribbon, which is traditionally a symbol of remembrance or mourning.

Ugh, so sad.

2012: Emma Ostilly

After his breakup with Caroline, Harry moved on with model Emma Ostilly. The two had some brief fun together, when paparazzi caught them kissing in what appeared to be a random archway somewhere in the blonde beauty’s homeland of New Zealand. Unfortunately, the fling didn’t last long as she lived thousands and thousands of miles away from the Brit — but, lucky for her, she got to star in the boy band’s music video for Gotta Be You. That is a definite plus!

Take a look (below) the ex-lovers in action:

2012: Emily Atack

It was rumored that Harry was dating the British starlet Emily Atack back in 2012, but she didn’t confirm the romance until 2014 in an interview with Reveal Magazine. At the time, she revealed to the glossy that it was casual fling, saying:

“We were never boyfriend and girlfriend… We had a short-lived thing that was just a bit of fun. Then, we went off in our opposite directions.”

It seemed pretty amicable to us!

2012: Caggie Dunlop

Jeez, Harry was pretty busy in the romance department in 2012! In July of that year, he was briefly seen with Caggie Dunlop, the star of the UK reality show, Made in Chelsea, after the twosome exchanged some flirty messages on Twitter. Unfortunately, the relationship ended soon after!

The TV personality allegedly couldn’t handle the crazy fans that always surrounded the boy band member. In an interview with Marie Claire, her co-star Millie Mackintosh spoke about the hookup, saying:

“It was horrible for Caggie. I’m not going to speak about it, but when people are showing up outside your parent’s house, it’s gone too far.”

The 31-year-old also added:

“Caggie is a fun-loving girl, I don’t think she minded the attention too much, but it does all get a bit much. There’s a different direction she wanted to go in, and I think she got a bit freaked out.”

We don’t blame you, girl! Directioners are dedicated, and a whole other level of brutal!

2012-2013: Taylor Swift

It’s hard to forget the iconic relationship between these two pop stars — especially since most of us have seen the photographic evidence of their famous date to the Central Park Zoo (Literally, it lives rent-free in our minds). There’s also the minor detail that many of their songs seem to catalog specific moments of their whirlwind relationship.

As you may know, Taylor Swift‘s hit songs, Style, Out of the Woods, I Knew You Were Trouble, …Ready for It, and I Wish You Would, were speculated to be about the famous pop crooner. In an interview with Rolling Stone in 2017, he addressed the rumors that some of the 31-year-old singer’s songs were about him, saying:

“I mean, I don’t know if they’re about me or not…but the issue is, she’s so good, they’re bloody everywhere. I write from my experiences; everyone does that. I’m lucky if everything [we went through together] helped create those songs. That’s what hits your heart.”

He continued, adding:

“In writing songs about stuff like that, I like tipping a hat to the time together. You’re celebrating the fact it was powerful and made you feel something, rather than, ‘This didn’t work out, and that’s bad. And if you run into that person, maybe it’s awkward, maybe you have to get drunk, but you shared something. Meeting someone new, sharing those experiences, it’s the best s**t ever. So thank you.”

Of course, Harry had to fire back with his emotional mid-tempo track Two Ghosts, which many believed to be about his relationship with Tay due to the description of a woman with the “same lips red, same blue eyes.”

You know, if all else, at least we can be thankful for all the great bops they produced since the end of their coupling. On to the next, as they say!

2013: Nicole Scherzinger

Here we began to see some very short-lived dalliances, starting with Harry and Nicole Scherzinger! In 2015, The Sun first reported that the lovers briefly hooked up two years prior. The Pussycat Dolls alum was a judge on The X-Factor when the actor was on it with his beloved boy band in 2010.

2013: Kimberly Stewart

It’s always the dads who can’t always keep the tea under wraps! In 2013, Rod Stewart let the cat out of the bag about the relationship between Harry and his daughter Kimberly Stewart. Speaking on Alan Carr’s TV talk show, Chatty Man, the British rock singer said:

“His [Harry’s] car was here in the morning. Let’s put it that way. But he may just have come round to pick something up…”

View this post on Instagram

A post shared by Kimberly Stewart (@thekimberlystewart)

Way to go there, Rod!

2013 – 2014: Kendall Jenner… Part 1!

Let us talk about a complicated past! In November 2013, the pair were first spotted having dinner in LA together. The affair didn’t last long, as they reportedly split in February 2014. However, they didn’t say goodbye for too long!

2014: Erin Foster

After the two were photographed together at a pumpkin patch in October 2014, rumors started swirling that Harry was dating Gigi and Bella Hadid’s ex-step sister, Erin Foster. The relationship didn’t go very far though — probably because of the 11-year-age gap, at least we can assume.

2014 – 2015: Nadine Leopold

It’s time to dive into the first of many Victoria Secret models that Harry dated. Sadly for Nadine Leopold, her fling was short-lived (but filled with many froyo outings), and they called it quit in March 2015.

2015: Sara Sampaio

In 2015, Harry was seen making out with Sara Sampaio in New York. The next day, the Portuguese Victoria’s Secret model left his hotel in the same clothes from the night before. YGG!

2015: Georgia Fowler

Harry briefly dated New Zealand model Georgia Fowler back in October 2015. At the time, many fans started to catch onto their entanglement after she posted a video on her Snapchat of the two playing Scrabble together (see the moment below).

Talk about wordplay.

While their romance was short-lived, it’s speculated that the singer’s song Kiwi is about the 28-year-old. In case you didn’t know, “kiwi” is a common nickname for folks from New Zealand. (The more you know!) However, Georgia hasn’t confirmed the rumors, claiming in an interview with The Morning Show that she didn’t “really know anything about it,” adding that she “definitely don’t have a baby…that’s what the song is all about.”

Interesting. What do U guys think? Is it about her?

2015 – 2016: Kendall Jenner… Part 2!

Rumors of Kendall and Harry’s relationship started flying again after they were seen on New Years’ together, getting rather cozy on a yacht. Our suspicions were later confirmed when Khloé Kardashian told Entertainment Tonight that the pair were an item, confessing:

“Do I think they’re dating? Yes. I don’t know if they’re like boyfriend-girlfriend. Nowadays I don’t know. People are weird with stuff. So, I don’t know their title.”

She continued, explaining:

“They were in St. Barts together hanging out. So to me, that’s dating. I would call that dating. [But] I don’t know what they are. You know, you have to have ‘the talk’ [and] I don’t know if they’ve had that talk yet.”

Merci, Koko, for that tip! However, things went quiet for a little bit until April 2016, when they were spotted shopping together in El Lay. In September 2016, the two were then seen at dinner, leading many to believe they were still together.

Can anyone else imagine Harry having dinner with the Kar-Jenner family at Nobu if they were still an item?? It would be pretty wild, to say the least!

2016: Pandora Lennard

According to a report in 2016 from The Sun, fashion stylist Pandora Lennard was spotted leaving Harry’s London pad after spending the night. The news came just a few weeks after the KUWTK star confirmed Kendall’s relationship with the Sweet Creature hitmaker AND the former couple’s romantic vacation to St. Barts.

At the time, a source close to Harry and Pandora expressed their shock to the outlet, claiming:

“Everyone knew they were attracted to each other, and they have been pals for a while, but we didn’t think anything would happen as Harry and Kendall are officially an item. This is gobsmacking.”

Indeed, it is as this could have possibly meant that the handsome man cheated on the then 20-year-old supermodel!

2017: Tess Ward

In the spring of 2017, Harry had spent some time with chef and food blogger Tess Ward. When they were first romantically linked together, an insider close to the Golden musician revealed Harry met the blond Brit in early February 2017 thanks to some mutual friends. By March of the same year, the pair began a relationship together, according to E! News.

However, Tess reportedly ended things in June 2017 to get back together with her ex-boyfriend. Must be rough, Harry!

2017 – 2018: Camille Rowe

Harry’s relationship with French model Camille Rowe — though not as public as others — could be his strongest relationship yet! The two reportedly dated for a little over a year, and everything seemed to be smooth sailing during that time. While dating, Harry reportedly introduced the VS model to his family. (GASP!) Unfortunately, though, the former lovers came to an abrupt end in July 2018.

A little over a year after the rumored split, one of Harry’s BFFs, Tom Hull, opened up to Rolling Stone about “this breakup that had a big impact on [Styles].” In the same interview, the singer didn’t mention Camille by name, but he said that his music was inspired by his personal life and relationships, including his heartbreaking relationship with the Playboy cover girl.

“For me, it doesn’t mean I’ll sit down and be like, ‘This is what I have for dinner, and this is where I eat every day, and this is what I do before I go to bed.’ But I will tell you that I can be really pathetic when I’m jealous. Feeling happier than I’ve ever been, sadder than I’ve ever been, feeling sorry for myself, being mad at myself, being petty and pitiful — it feels really different to share that.”

On Harry’s latest album, Fine Line, many lyrics seemed to allude to his relationship with the face of Chloé. But the most telling song was Cherry, which seemingly pointed to the fashion lady’s Parisian roots and even included a voicemail from a woman speaking French at the end of the track.

Despite everything, the exes still seem to be friends. In an interview with Apple Music’s Zane Lowe in November 2019, Styles discussed his decision to add the message, and he pretty much confirmed it came from Camille, saying:

“It got added in later on, and it felt so part of the song. It just felt like it needed it. We’re friends and stuff, so I asked her if it was OK. And she was OK with it.”

Listen to the song (below), the voicemail starts at 3:47:

The world may never know what exactly went down between the former couple, but it still makes us smile at the fact they are still cool with each other!

2019: Kiko Mizuhara

Harry was romantically connected to Kiko Mizuhara when rumors started spreading in early 2019; however, the model quickly shut them down when she tweeted that she never met the singer at the time.

“It has been reported that I and Harry Styles are dating, but I have never been dating him, and I have never met him. Everyone, the world is full of fake news. Don’t let the media dance!”

私とハリー スタイルズさんが交際しているとの報道が出ておりますが、彼との交際の事実もありませんし、1度もお会いした事もありません???? 皆さま、、この世はフェイクニュースだらけ。くれぐれもマスコミには踊らされないように、、ね！

— Kiko Mizuhara ???? 水原希子 (@kikoxxx) January 14, 2019

One month later, though, she was spotted at Harry’s 25th birthday party in Tokyo. In the video posted on social media, the two clearly knew each other, but they didn’t seem like a couple. Shortly after, the dating speculation died down.

Harry with Bobby Berk and Kiko tonight in Tokyo, Japan – February 2 (via bobbyberk) pic.twitter.com/XYb6llWzW1

— HSD (@hsdaily) February 2, 2019

2021: Olivia Wilde

As we mentioned before, Harry has most recently been dating Olivia Wilde. According to People, the couple has been with each other for some time. Nonetheless, the timeline of their relationship has been a bit of a doozy.

In November 2020, the actress announced the end of her seven-year engagement to Jason Sudeikis. One source asserted to Us Weekly that Olivia ended things with the 45-year-old star early in 2020, while another insider said that it happened “after she already had gotten close to Harry.” Then, a third source insisted that he “did not break up an engagement.”

We will just have to wait and see how the cards fall! But here’s hoping one of them speaks out about their coupling soon because we need some more deets! Or maybe another song from the music man?!

Okay, Perezcious readers, what relationship of Harry’s was your all-time favorite? Which rumored entanglement do U think is true? Let us know in the comments (below)!

[Image via Ivan Nikolov/WENN, WENN, Nicky Nelson/WENN, Fayes Vision/WENN, Apega/WENN, & Nicky Nelson/WENN]

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