As you may or may not be acutely aware: Harry Styles is once again single after ending his, erm, traumatizing (not for him, def for me) ’ship with Olivia Wilde. And although it’s unclear who will be next on his roster, I feel as though it’ll likely be a fellow Grammy winner or an Insta-famous model or someone whose name rhymes with Fendall Kenner—especially given his track record. I mean, seriously, the former One Direction star and his hair coif have dated some major A-list celebrities, including Cara Delevingne and Taylor Swift, and the time has come to look back at his dating history because truly what else is there to do during the winter of our curiosity, ya know?
Emily Ratajkowski: 2023 to ?
Harry and Emily were spotted sloppily making out next to a car in Tokyo, but TBD on how serious the relationship is. For now, everyone is in a state of shock and merely processing this brand! new! info! (perhaps including Olivia Wilde, who previously dated Harry and attended one of his shows with EmRata).
Kendall Jenner (Again?!?!?): 2022
The report (read: rumor) came courtesy of The Sun, which claimed that sources ~in the mix~ said that Harry had been reconnecting with his ex Kendall Jenner amid his split from Olivia and hers from Devin Booker. “Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another. And Harry has had Kendall’s ear over his breakup with Olivia,” someone described as “one L.A. source” (lol) said. “Kendall is one of the few people to understand the level of fame and scrutiny which Harry endures. She is also dealing with her own tough time.” In-ter-est-ing!
Olivia Wilde: 2021 to 2022
If you want a full timeline of Olivia and Harry’s whole thing, we’ve got you covered, but the highlights go a lil something like this:
Kiko Mizuhara: 2019
Harry and model Kiko Mizuhara were linked in April 2019, but honestly? Evidence of a relationship between these two is iffy at best. And by that I mean…the Daily Mail reported they were dating based on a mutual Instagram follow. Which on the one hand makes sense because if Harry Styles followed me, I’d also assume we were dating, but on the other hand is objectively outrageous????
Either way, Kiko shut sh*t down in a series of tweets, writing, “It has been reported that Harry Styles and I have been in a relationship, but I have no relationship with him, and I have never met him.…People believe what they want to believe rather than questioning reality.”
Camille Rowe: 2017 to 2018
Harry and model Camille Rowe dated for an entire year before splitting up in summer 2018, but clearly, their relationship had a big impact on Harry because he used a voicemail Camille left him on the song “Cherry.” The translation?
“Hello! Are you asleep? Oh, I’m sorry….”
“Well, no…nope, it’s not important….”
“Well then…we went to the beach and now we—”
“Perfect! Harry—”
Harry spoke about using said voicemail to Apple’s Zane Lowe, saying, “When we listened back to the album, I asked her to add it in. I wanted [‘Cherry’] to reflect how I felt then. I was feeling not great. It’s all about being not great. Because you get petty when things don’t go the way you want it. There’s parts that’s so pathetic.”
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Tess Ward: 2017
Harry dated food writer Tess Ward in spring 2017, and a source told Page Six that “they really bonded over their mutual love of quirky fashion and food—and things turned romantic quickly.” Oh, and “this really seems different to Harry’s past relationships as Harry genuinely is besotted with Tess and doesn’t want to risk messing this one up.”
Plot twist: They broke up by summer.
Kendall Jenner: 2013 to 2016 (On and Off!)
Kendall and Harry have been hooking up on and off for literally ever, including that legendary time they were photographed making out on a boat. These two have serious chemistry, and if you don’t believe me, I have evidence.
Exhibit A: Kendall and Harry vibing at the Met Gala:
Exhibit B: Harry interviewing Kendall on The Late Late Show, where the tension is simply off the charts.
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Georgia Fowler: 2015
Harry briefly dated model Georgia Fowler in 2015, and fans are convinced he wrote “Kiwi” about her.
Georgia responded to the rumors by saying “Ah, don’t really know anything about it” and by calling Harry a friend. Kay, fine, but just gonna leave this here for you to read into:
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Sara Sampaio: Earlier 2015
Before Harry was linked to Georgia, model Sara Sampaio was photographed leaving his New York hotel wearing the same outfit she wore the night before. Could mean nothing, could mean all the things, you decide.
Nadine Leopold: Even Earlier 2015
Harry and model Nadine Leopold ended their very short relationship in March 2015, with a source telling Heat magazine that “she’s told Harry she’s simply too busy to date him” and that “Harry is gutted. He’s never been dumped before, so it’s a real punch in the stomach for him.”
Erin Foster: 2014
I know, right! Harry and Erin Foster were briefly linked in October 2014, when they were spotted pumpkin shopping in L.A., as one does. A source told E! at the time, “It’s unlikely it will ever become serious, but they are casually dating whenever they are in the same place at the same time and it works for both of them.”
Nicole Scherzinger: 2013
According to a source who spoke to The Sun, Harry and Nicole “had a dalliance at the end of The X Factor in 2013” and then “hooked up over three years later when Harry had matured and was a member of the world’s biggest band.” They never confirmed the fling, but Nicole did step out in a Harry Styles T-shirt once, so!
Kimberly Stewart: Also 2013
We only know about this one because Rod Stewart put Harry on blast, saying, “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….”
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Taylor Swift: 2012 to 2013
While some cynics argue this was a PR relationship, Taylor and Harry certainly did the most during the three months they were together. By which I mean they went on a very public walk around Central Park Zoo and Taylor started to not-so-subtly wear Harry’s paper airplane necklace, which she then ripped off in the “Out of the Woods” music video after they broke up.
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Another awk thing that happened post-Haylor split? Taylor dissed Harry during her 2013 Grammys performance by using an English accent. Truly ????.
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Emily Atack: 2012
This ’ship was short and sweet, which Emily confirmed in an interview several years back:
“We were never boyfriend and girlfriend. I think that’s the first time I’ve ever admitted to what it was, because I’ve always just shrugged it off before. But I think it’s best to clear it up. So yeah, we had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions. Harry and I had a laugh. It was brief but fun, and then we moved on. We haven’t spoken in a while—he’s one of the most famous people in the world now.”
Emma Ostilly: Also 2012
Harry and Emma were seen kissing in New Zealand after they met on the set of the video for “Gotta Be You.” Memories!
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Caroline Flack: 2011
Harry and the late X Factor presenter Caroline Flack were linked in 2011, and she revealed that they did, in fact, have a relationship when Harry was 17 and she was 31. Caroline also opened up about how hard the scrutiny was for her in her memoir:
“We were both single, we got on well, and we had a laugh. It was only when it became public knowledge that things turned sour.”
That’s it, but obviously we’ll be updating this with any important Harry Styles developments.
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