Ever since his boy band days, Harry Styles\u2019 love life has been a topic of conversation. Although the \u201cWatermelon Sugar\u201d singer has gotten more and more private about his romances over the years, that hasn\u2019t put a stop to the public\u2019s interest. In October, that only became more obvious when Taylor Swift \u2014 arguably Styles\u2019 most famous ex \u2014 re-released 1989<\/em>, much of which fans think was written about their relationship<\/a>. Specifically, Swift\u2019s vault track \u201cIs It Over Now?\u201d<\/a> seemed to shed light on their brief but memorable romance, according to fan speculation<\/a>.<\/p>\n In the song, Swift sings about an on-and-off situation with an ex, specifically someone who had a habit of dating her \u201cclone.\u201d The most damning lyrics go: \u201cIf she\u2019s got blue eyes, I will surmise that you\u2019ll probably date her … You search in every model\u2019s bed for something greater, baby.\u201d<\/p>\n Although Swift has not confirmed the lyrics are about anyone in particular (and she does write fictional stories in many of her songs), many fans believe the song is a dig at Styles. His dating history can shed some light on why they\u2019re so convinced, despite a lack of serious evidence.<\/p>\n It all started in 2007 with Styles\u2019 hometown girlfriend. Abigail Crawshaw. According to\u00a0J-14<\/i>,\u00a0Styles and Crawshaw dated when the singer was 12<\/a>, and the two have remained friends post-breakup. He even invited Crawshaw to some One\u00a0Direction\u00a0shows<\/a> over the years.<\/p>\n Caroline Flack and Harry Styles kicked things off back in 2011. Flack, a TV presenter and Love Island <\/em>host, met Styles on the set of X-Factor.<\/em>\u00a0Styles was 17 years old, while Flack was 31. In 2015, she discussed the age gap<\/a> in an interview with People<\/em>, saying, \u201cI’ve never felt I was much older than Harry anyway. I still feel 18 and probably act that way half the time.\u201d<\/p>\n They broke up in 2012, with Styles confirming the split on Twitter in January of that year. “Please know I didn’t ‘dump’ Caroline<\/a>. This was a mutual decision,\u201d he wrote, per BBC<\/em>. “She is one of the kindest, sweetest people I know. Please respect that.”<\/p>\n Emma Ostilly and Styles reportedly began their romance<\/a> in April 2012, soon after his breakup with Flack. The duo met when Ostilly starred in One Direction\u2019s “Gotta Be You” music video, but they were only spotted kissing once post-filming.<\/p>\n Styles and British actor Emily Atack reportedly had a brief fling in May 2012. She addressed the rumors in a 2013 interview with Reveal Magazine<\/em>, per Hello!: “We were never boyfriend and girlfriend<\/a>. I think that’s the first time I’ve ever admitted to what it was, because I’ve always just shrugged it off before.\u201d<\/p>\n Atack added, “We had a short-lived thing that was just a bit of fun. Then we went off in our opposite directions.” She made it clear there were no hard feelings. \u201cHarry and I had a laugh. It was brief, but fun, and then we moved on.\u201d<\/p>\n Swift and Styles\u2019 romance was short-lived; they only dated from late November 2012 to January 2013. The pair was spotted together only a few times, but their connection wasn\u2019t exactly a secret, especially post-breakup \u2014 lest we forget Swift appearing to imitate Styles\u2019 British accent<\/a> during her performance of \u201cWe Are Never Getting Back Together\u201d at the 2013 Grammys. <\/p>\n After they both released music seemingly about each other<\/a> (see: \u201cStyle,\u201d \u201cOut of the Woods,\u201d<\/a> \u201cPerfect,\u201d and \u201cTwo Ghosts\u201d), the duo seemed to be on good terms. In 2017, Styles called their romance a \u201clearning experience\u201d<\/a> in an interview with Rolling Stone<\/em>.<\/p>\n In 2020, he said Swift\u2019s songs about him were \u201cflattering.\u201d At the time, he told Howard Stern, \u201cI think it\u2019s, like, flattering. Even if the song isn\u2019t that flattering, you still spent time on it and ultimately, using Taylor as an example, she\u2019s a great songwriter.<\/a> So they\u2019re good songs.\u201d<\/p>\n After splitting from Swift, Styles reportedly dated Victoria\u2019s Secret model Nadine Leopold. \u201cHarry has been getting more serious with Nadine<\/a>,\u201d a source told Us Weekly <\/em>in January 2015. Though they weren\u2019t official at the time, the insider claimed they had been \u201cspending lots of time together\u201d since meeting through her agent in November 2014. <\/p>\n Styles spent time with another Victoria\u2019s Secret model next, according to rumors. In photos obtained by the Daily Mail<\/em> in June 2015, Styles was seen kissing Sara Sampaio<\/a> in New York City. They reportedly spent the night at the same hotel that same week, too. <\/p>\n Styles was rumored to be dating (another!) Victoria\u2019s Secret model, Georgia Fowler,<\/a> after she shared a video of them playing Scrabble on Snapchat. Since Fowler is from New Zealand, fans think the Styles\u2019 song \u201cKiwi\u201d might be about her. <\/p>\n She addressed the rumors on \u201cThe Morning Show,\u201d an Australian talk show, in 2017, saying, \u201cI don’t really know anything about it \u2014 definitely didn’t have a baby. That’s what the song’s all about<\/a> so I think it’s highly unlikely.\u201d (The lyrics go: \u201cI think I’m losin’ it, oh, I think she said \/ I’m having your baby \/ It’s none of your business.\u201d)<\/p>\n This relationship really threw the world for a loop. In December 2015, Kendall Jenner and Styles were first spotted in St. Barts<\/a>\u00a0together, and their PDA-filled yacht date was telling.<\/p>\n Though Styles and Jenner stayed mum on the rumors, Jenner\u2019s older sis Khlo\u00e9 Kardashian admitted they were an item<\/a> in a 2016 interview. \u201cThey 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,\u2019\u201d Khlo\u00e9 said at the time.<\/p>\n Turns out, Styles had a bit of a thing for models. In 2017, romantic rumors spread about him and Victoria\u2019s Secret model Camille Rowe<\/a> after they were spotted together in NYC. At the time, the Daily Mail <\/em>reported that Styles was \u201cbesotted\u201d with Rowe<\/a>.<\/p>\n Though the duo never confirmed a relationship, when Styles came out with \u201cCherry\u201d in 2019, he included a voicemail from Rowe<\/a> in it. He also sang of their former romance, “I just miss your accent and your friends.\u201d (She has a French accent.)<\/p>\n In January 2021, Wilde and Styles were spotted holding hands<\/a> at his agent’s wedding. Though they mostly kept quiet on their romance, the duo did drop a few hints about their \u2018ship. In December 2021, Wilde told Vogue<\/em> that she was \u201chappier than ever\u201d<\/a> in life. And in May 2022, Styles referenced \u201ctrust[ing]\u201d Wilde<\/a> as a director while shooting Don\u2019t Worry Darling<\/a><\/em>. He also seemed to allude to her<\/a> in his song, \u201cAs It Was,\u201d with the line, \u201cLeave America, two kids follow her.\u201d<\/p>\n In November 2022, People <\/em>reported that the couple was \u201ctaking a break.\u201d<\/a> And in December 2022, Wilde was reportedly still hurting<\/a> after the split. On Dec. 8, an insider told Us Weekly<\/em>, \u201cOlivia is still very much upset<\/a> about the breakup,\u201d adding that she\u2019s been \u201ctrying to move on.\u201d<\/p>\n Styles and Emily Ratajkowski<\/a> had a very public makeout in March 2023, following their respective breakups. In a video obtained by the Daily Mail<\/em>, the duo was seen kissing on a street in Tokyo after Styles performed there for Love On Tour.<\/p>\n A month later, EmRata spoke to Vogue <\/em>about fans\u2019 reactions to her and Styles\u2019 makeout \u2014 and her main takeaway had to do with Styles\u2019 ex, Wilde, and all the attention she was receiving when they dated. \u201cI feel bad for Olivia<\/a>, because she had to suffer this situation on several occasions<\/a>,\u201d Ratajkowski said at the time. <\/p>\n Dating rumors surrounding Styles and Taylor Russell<\/a> began after she attended his concert in Vienna \u2014 and sat in the VIP section, according to TMZ footage<\/a>. Per Page Six, they were also photographed holding hands<\/a> as they explored the Austrian city.<\/p>\n In August, more proof of their connection came to light when Styles attended Russell\u2019s play in London and hugged her post-show<\/a>. Per Page Six, they remained close at the afterparty and left together.<\/p>\n2007: Abigail Crawshaw<\/h2>\n
2011: Caroline Flack<\/h2>\n
![\"Who](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2022\/5\/19\/0ac25170-356b-4e89-9527-dba1357d79aa-getty-1184748262.jpg?w=760&h=1140&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>April 2012: Emma Ostilly<\/h2>\n
![\"Emma](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2023\/11\/2\/361faaa7-6632-4a90-9a33-7d14c1761a3d-getty-151246317.jpg?w=760&h=1096&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>May 2012: Emily Atack<\/h2>\n
![\"Emily](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2023\/11\/1\/601630ac-598c-4edc-9392-b94856fac4d9-getty-154267075.jpg?w=760&h=1139&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>2012-2013: Taylor Swift<\/h2>\n
![\"Harry](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2022\/5\/19\/57a7fa2e-b93f-4914-9e77-cecd198feec8-getty-474684579.jpg?w=760&h=1106&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>2014-2015: Nadine Leopold<\/h2>\n
![\"Nadine](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2023\/11\/2\/a7a34213-07a7-4b77-a46c-dc49e1a36b60-getty-494747110.jpg?w=760&h=1140&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>June 2015: Sara Sampaio<\/h2>\n
![\"Sara](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2023\/11\/2\/a5fad944-b90d-4c00-8154-2082562d2fb5-getty-499831174.jpg?w=760&h=518&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>October 2015: Georgia Fowler<\/h2>\n
![\"Georgia](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2023\/11\/2\/8c0a5e0f-22d2-4be3-ad86-3bdeffaba7b7-getty-494868992.jpg?w=760&h=1046&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>2015-2016: Kendall Jenner<\/h2>\n
![\"Harry](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2022\/5\/19\/6fedb1a2-df4e-4ada-a8fd-c29c68ec63e2-getty-1147444311.jpg?w=760&h=507&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>2017: Camille Rowe<\/h2>\n
![\"Harry](\"https:\/\/imgix.bustle.com\/elite-daily\/2017\/08\/03155726\/harry-styles-and-camille-rowe.jpg?w=760&h=378&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>Early 2021-November 2022: Olivia Wilde<\/h2>\n
![\"Harry](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2022\/5\/19\/d364761d-642f-415b-a786-0fd979e1cd92-getty-1386918167.jpg?w=760&h=608&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>March 2023: Emily Ratajkowski<\/h2>\n
![\"Emily](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2023\/11\/2\/89a4fd97-df17-4445-b548-7b860d25ba05-getty-1754616784.jpg?w=760&h=507&fit=crop&crop=faces&auto=format%2Ccompress)
<\/picture><\/noscript><\/div>June 2023-Present: Taylor Russell<\/h2>\n
![\"Taylor](\"https:\/\/imgix.bustle.com\/uploads\/getty\/2023\/11\/2\/52c9df35-32d0-4cd6-a66b-70a947a97dba-getty-1603916535.jpg?w=760&h=1140&fit=crop&crop=faces&auto=format%2Ccompress)
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