Caroline Flack

Way back in Harry's X Factor days in late 2011 and early 2012, he was linked to the show's host, Caroline Flack. This was Harry's first high-profile romance, but things ended when the public caught wind of it. In January 2012, Harry reacted to their split on Twitter [8], writing, "She is one of the kindest, sweetest people I know. Please respect that." Following Caroline's death [9] in February 2020, Harry seemingly paid tribute to her by wearing a black remembrance ribbon [10] to the BRIT Awards.

Emma Ostilly

Emma, who starred in One Direction's "Gotta Be You" video [11] way back when, had some fun with Harry in late 2012 right around when he started talking to Taylor. The fact that she lived in New Zealand at the time put a damper on what may have been a relationship, though, so it ended up just being a whirlwind fling.

Taylor Swift

Ah, the Taylor Swift [12] days. While many believe this relationship was solely for the purpose of publicity, the fact remains that the two were linked for a period of a few months in late 2012 into early 2013. After "breaking up," Taylor went on to write several songs supposedly about Harry [13] ("Style" and "Out of the Woods" just to name a couple), which is something no one ever would have expected (kidding). In turn, Harry has also possibly written a few songs right back for her [14], like one of One Direction's last singles, "Perfect," and his recent solo song "Ever Since New York."

Cara Delevingne

Harry and Cara have been friendly for years, and while it was rumoured that they dated at one point in 2013, there was never any confirmation from either party. In fact, Harry dodged the question while at a Burberry fashion show that Cara was walking in.

Kendall Jenner

Harry and Kendall have been friends for several years and have had an on-again, off-again thing for most of it. Rumours of their relationship hit a new level when they were photographed getting very cosy on a yacht in the Caribbean [15] during the holidays in late 2015. They still get together from time to time because of their close friendship, but it seems like things never really got serious.

Kara Rose Marshall

Harry was rumoured to be dating model Kara Rose after they were seen hanging out in New York with Harry's hairstylist back in 2013. If it was, in fact, a relationship, it didn't last long.

Kimberly Stewart

Rod Stewart himself let it slip in 2013 that Harry spent the night [16] at his house when he was rumoured to be dating Kimberly, his daughter. But this one, like all the rest of Harry's relationships, was short-lived.

Paige Reifler

In 2014, Harry was spotted in a few social media photos with model Paige Reifler before stepping out with her a couple times. However, things got messy when she supposedly poked fun at him on her friends' Instagrams and insinuated she might be using him for his fame.

Nadine Leopold

There's an ongoing joke that Harry has a winter girlfriend every year. In 2012 it was Taylor, in 2013 it was Kendall, and in winter 2014, which rolled over into early 2015, it was Nadine. Harry and the model spent a lot of time together in LA before Harry and the rest of One Direction embarked on their last tour, but the relationship was short-lived.

Sara Sampaio

Sara and Harry briefly dated or hung out in 2015, not long after he and Nadine reportedly broke up. Interestingly, Sara and Nadine were very good friends — and both models — and the Harry factor supposedly caused a bit of a rift between them.

Georgia Fowler

Harry had a brief thing with model Georgia back in 2015 that everyone found out about when she Snapchatted a video of them playing scrabble together at a spa resort in England. Though she took the Snapchats down pretty quickly after posting, we all know everything lives forever on the internet.

Tess Ward

Harry's current girlfriend [17] is social media influencer and chef Tess Ward. Their new relationship [18] was exclusively revealed in The Sun, something that Harry has never allowed in the past. The supposed relationship quickly fizzled, though.

Camille Rowe

One of Harry's most-publicised romances was with French Victoria's Secret model Camille Rowe. Fans discovered the two were dating after they heard Harry's voice in Camille's Instagram story [19]. Throughout their romance — which lasted from summer 2017 to July 2018 [20] — the duo became extremely close, and Harry even introduced Camille to his family. However, the two eventually decided to part ways.

Harry addressed their split in his song "Cherry" from his 2019 album Fine Line [21]. "I just miss your accent and your friends," he croons. The singer also included an old voicemail from Camille [22] at the end of the track.

Olivia Wilde

After working together on "Don't Worry Darling," [23] which Styles and Wilde star in, the two sparked romance rumors [24] when they were spotted holding hands at a friend's wedding in January 2021. A source told People [25], "They were affectionate around their friends, held hands, and looked very happy. They have dated for a few weeks."

Over the course of 2021, the duo would be seen together in various locations around the world, from the UK to Italy. In July 2021, the two were photographed kissing in Tuscany, further solidifying the dating rumours. However, nothing was officially confirmed until January 2022 when Wilde sat down with Vogue [26] and discussed her relationship with Styles.

"It's obviously really tempting to correct a false narrative," she said. "But I think what you realise is that when you're really happy, it doesn't matter what strangers think about you. All that matters to you is what's real, and what you love, and who you love."

In May 2022, the two were spotted vacationing [27] together in Italy. The photos came just weeks after Wilde was served legal papers stemming from her child-custody battle with her ex-fiancé, Jason Sudeikis, while on stage at CinemaCon, per Us Weekly [28].

The September 2022 release of "Don't Worry Darling" was, unfortunately, marred with controversy and speculation surrounding the couple as well. It all reached a fever pitch during the Venice premiere. The couple kept things super professional, forgoing walking the carpet together or sitting next to each other during the showing. (Although if they had sat together, they may have avoided all the speculation that Styles spit on his costar Chris Pine [29].)

In October of that year, Wilde and Styles were unwillingly dragged into more speculation when Wilde's former nanny claimed to the Daily Mail in an Oct. 17 article that Jason Sudeikis once threw himself [30] in front of Wilde's car to stop her from visiting Styles with some of her reported special salad dressing [31] in the final days of her tenure with the former couple. (Wilde and Sudeikis adamantly denied the rumors in a joint statement to POPSUGAR.)

The two officially split in November 2022. At the time, a source told People [32] that they were "taking a break."

Emily Ratajkowski

In late March, Styles and Emily Ratajkowski were spotted kissing in Japan as seen in a video and photos obtained by the Daily Mail [33]. At this point, it's unclear whether the "Watermelon Sugar" singer and the model are dating or simply hanging out.