Harries, listen up.
IMHO, Harry Styles can do no wrong. He's a boy band survivor, a pop singing genius, and a movie star. What can't he do? No, seriously, I'd really like to know. Not to mention, the man is a serious charmer (I mean, have you heard “Falling”?), and he doesn’t seem to have one type. In the past, Styles has gone for hometown sweethearts to celebrity superstars to one very special mother of two (who also happens to be a successful actor and director — layers, people!). OK, OK, so he’s clearly got some history, but who exactly has Harry Styles dated? Let’s take a gander, shall we?
I’ve been keeping tabs on each of Styles’ paramours — even his first girlfriend from back in 2007. And TBH, it's kind of impressive that he even has time to date considering he releases new music constantly, performs on the reg, and stars in feature films. Most recently, Styles was cast in the film Don’t Worry Darling, AKA where he met current girlfriend Olivia Wilde. (And yes, I’ve been rewatching the steamy trailer ever since.)
Whether or not you share my crush on Styles, I think we can all agree that his romantic history is of interest. (Right? Right?) So to appease everyone’s (see: mine) curiosity, here’s a comprehensive list of everyone who has been linked to the singer/actor/icon. You're welcome.
Abigail Crawshaw: 2007
Styles’ romantic life all started in 2007 with his hometown girlfriend. Abigail Crawshaw. According to J-14, Styles and Crawshaw dated when the singer was 12 (truly a baby), and the two have remained friends post-breakup. He even invited Crawshaw to some One Direction shows over the years. What a guy! Abigail, wherever you are, glad to have you as the founding member of the Harry Styles' Girlfriend Club.
Caroline Flack: 2011
Caroline Flack and Harry Styles kicked things off back in 2011. Flack, a TV presenter and Love Island host, met Styles on the set of X-Factor. Styles was only 17 years old, while Flack was... well, older. She was actually 31 when she started dating Styles. In 2015, Caroline Flack actually discussed the age gap in an interview with People,
I've never felt I was much older than Harry anyway. I still feel 18 and probably act that way half the time.
Emma Ostilly: 2012
Emma Ostilly and Styles began their romance in 2012, pretty soon after his breakup with Flack. The duo met when Ostilly starred in the One Direction’s "Gotta Be You" music video, but their rumored relationship did not last long. I guess it did not ~gotta be~ her, after all.
Taylor Swift: 2012 - 2013
Ah, Haylor. What a time to be alive. Though Taylor Swift and Styles’ romance only lasted for one year, from 2012 to 2013, it was truly glorious. (And it gave us the gift of Swift’s “Style,” so I count that as a win.) Through the course of their romance, the pair was only spotted together a few times, their connection wasn’t exactly a secret... lest we forget Swift imitating Styles’ British accent during her “We Are Never Getting Back Together” at the 2013 Grammys.
After the two split, Styles discussed the relationship in a very uncomfortable radio interview. Styles was asked about his song, "Two Ghosts" to which he replied,
I mean I think it's pretty like self-explanatory… Help me, Jeffry… I think, you know, it's about sometimes things change and you can be, you know, do all the same things and sometimes it's just different. You know?
Um, no, I don’t know. But it sounds complicated.
Kendall Jenner: 2015 - 2016
OK, so this relationship really threw the world (and me) for a loop. In Dec. 2015, Kendall Jenner and Styles were first spotted in St. Barts together, and their yacht date was v telling. (If The Bachelor franchise has taught me anything, it’s that dates are categorically more romantic when they involve boats.) Though Styles and Jenner stayed mum on the rumors, Jenner’s older sis Khloé Kardashian admitted they were an item in a 2016 interview. “They were hanging out together. 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,’” Kardashian said. Gotta love her willingness to spill the tea.
Camille Rowe: 2017
Turns out, Styles had a bit of a thing for models. In 2017, romantic rumors spread about him and Victoria’s Secret model Camille Rowe after they were spotted together in NYC. At the time, the Daily Mail reported that Styles was “besotted” with Rowe. Though the duo never confirmed a relationship when they were together, when Styles came out with “Cherry” in 2019, he included a voicemail from Rowe in it. He also sang of their former romance, "I just miss your accent and your friends.” (BTW, she has a French accent, in case you want to start practicing yours now.)
Olivia Wilde: 2021 - Present
In Jan. 2021, Wilde and Styles were spotted holding hands at his agent's wedding, and they’ve been pretty solid ever since. Though they’ve kept quiet on their romance, the duo has dropped a few hints about their romance. In Dec. 2021, Wilde did tell Vogue that she was “happier than ever” in life. And in May 2022, Styles referenced “trusting” Wilde as a director while shooting Don’t Worry Darling... it wasn’t the most romantic quote ever, but Styles also referenced his current leading lady in his latest single. “Leave America, two kids follow her,” he sang in “As It Was.” IDK about you, but I wouldn’t mind being Styles’ muse — even if the lyrics are a lil vague.
Happy for the two of them — even if I’m kinda hoping a spot opens up in the Harry Styles' Girlfriend Club.
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