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A brief history of every person Harry Styles has ever dated

How can one person’s type be Kendall Jenner *and* T Swift? It just doesn’t make sense!

Harry Styles dating history is such a murky pond of exes that even I, a renowned Harry Styles aficionado, was unaware of some of the characters from his past. Everything you thought you knew about Harry’s dating history is about to be revealed as… well, not a lie, but just super lacking in knowledge. For instance, did you know one of Harry Styles’ exes is Caggie Dunlop of MiC fame? Did you know one is Nicole Scherzinger? No, I bet you didn’t. But you’re about to find out so much more.

From the Taylor Swifts to the Kendalls to the countless models I can’t even bear to follow on Instagram for want of good mental health, here are all of Harry Styles’ exes.

2011: Caroline Flack

Harry and Caroline dated in 2011 after One Direction’s appearance on The X Factor, which Caroline was presenting at the time. At this point, Harry was 17 and Caroline was 32. Their relationship attracted a lot of attention because of the 15 year age gap, but the two broke up within a year. During their relationship, Caroline received death threats from Directioners and allegedly had people shout “paedophile” at her in the streets. Recently Harry paid tribute to Caroline following her death by wearing a black remembrance ribbon on his lapel at the 2020 BRIT awards.

2012: Emma Ostilly


Harry dated American model Emma Ostilly after Caroline and she even got an appearance in the music video for Gotta Be You, which is an underrated banger in my opinion. This was eight years ago though, and now Emma is married (and has been for a whole year!). Her husband is also pretty fucking fit. Just saying. Like seriously it’s hard to not downgrade from Harry Styles but she managed it well.

2012: Emily Atack

The pair never “officially” dated but they were seeing each other in this year. Atack told Reveal magazine: “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.” Lucky gal.

Still 2012: Caggie Dunlop

YEP. WHO KNEW? The original Made in Chelsea queen and It Girl for all of… two years? At this point, Harry would have been 18 and Caggie would have been 23. The man has a thing for older women, clearly. Or maybe he was just mature beyond his years at this point. There are lots of ways we can see it, but the main takeaway I’m getting is that he probably wouldn’t have dated me when I was 13… as much as I chose to believe the opposite.

2012-2013: Taylor Swift

The biggie. The two were pretty public from the beginning – they had their second ever date in Central Park and the paparazzi went a bit mental – then stayed together for around a year. After the relationship, multiple songs with cryptic lyrics about the Harry/Taylor relationship ensued – more on Taylor’s part than Harry’s though, characteristically. Out of the Woods, Style and I Knew You Were Trouble are all apparently about Harry. As for Harry, Perfect and Two Ghosts are allegedly about Taylor. Honestly, the most important takeaway from this relationship is when Taylor put on a fake English accent in her “We are never ever getting back together” Grammy’s performance to impersonate Harry and it was truly ridiculous. I love this level of pettiness. Skip to 2.18 for “Eye steel lov yew.”

2013: Nicole Scherzinger

Like I said: older women. It’s a running theme! Harry and Nicole were rumoured to be dating in 2013. By this point, Harry was apparently into his nineteenth year, and Nicole was 35. A 16 year age gap there, even bigger than him and Caroline. Yikes.

2013-2014: Kendall Jenner

via Instagram @kendalljenner

Ah, biggie numero dos. Harry and Kendall were spotted having dinner in LA in late 2013, only to break up by early 2014. It was shortlived, but it wasn’t the last time these two would do the tango.

2015: Georgia Fowler

Harry dated New Zealand model Georgia Fowler in 2015 for a short period of time. Apparently the song Kiwi is about her, but she denies any knowledge of this. However, she did post a cute video of her and Harry playing scrabble on her Snap story in 2015. Oh, back in the days of snap stories. (My favourite part of this video is that the uploader’s caption is “She’s his friend maybe?”. The denial is palpable)

2015-2016: Kendall Jenner 2 – Too Kendall Too Jenner

The two were spotted getting frisky together on a yacht in St Barts on NYE and Khloe Kardashian confirmed the pair were dating a week later.

Since then there’s been loads of rumours of them getting back together, but nothing substantial. Their history was double confirmed in 2019 with a cute duo appearance on James Corden’s Late Late Show and an overshare from Caitlyn Jenner, who said she wanted the pair to reunite. The two recently met up in lockdown, but Kendall has a new boyf so all bets are off on that one.

2017-2018: Camille Rowe

Next in the pile of Harry Styles’ exes is the big ex: Camille. Victoria’s Secret model Camille Rowe and Harry were together for around a year but ended things in 2018. Allegedly a lot of songs on Harry’s latest album, Fine Line, are about Camille – including sad bop “Falling”. Camille is also older, currently aged 34. At the time they were dating Camille would have been 31 and Harry 23. Do you see this pattern!! Do you see it!

Also, she is – and I cannot stress this enough – very fit and very cool.

2019: Kiko Mizuhara

This is nothing more than a rumour, but Harry and Kiko were said to be dating at points last year. In a tweet posted in Jan 2019 she denied having ever met Harry but then was filmed standing next to him on Queer Eye star Bobby Berk’s IG story a month later. Coinkydink? I think not.

2020: ??? No one ???

From what we know, Harry Styles is currently single. There’s no telling who his next fling could be with. Which means there’s a one in eight billion chance it could be YOU! Or Kendall Jenner again. Probs more likely I guess.

Featured image (before edits) by Annie Spratt on Unsplash

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