Harry Styles' Many Ladies: Kendall Jenner, Taylor Swift, Cara Delevingne & More!

Take a look at the One Direction hunk's long dating record!

By Bruna Nessif Nov 22, 2013 12:22 AMTags
Kendall Jenner, Harry Styles, DateNGRE/AKM-GSI

Harry Styles is a hot young thing desired by many—and he knows it.

The One Direction singer seems to be making the most of his time as a successful 19-year-old celeb by enjoying the company of numerous beautiful ladies, the most recent being E!'s own Kendall Jenner. The pair was spotted leaving West Hollywood restaurant Craig's last night, but don't bust out the new couple alert just yet.

A source tells E! News, "They aren't 'dating.' They are just friends. That was like the first real time they hung out. We will see what happens."

Yeah, we've heard that before. So while we wait to see if a romance sparks between these two, let's take a look back at surprising Styles' dating past.


1. Lucy Horobin: Let's kick this off with a tale that was a bit scandalous, according to reports. One of Styles' first public romances appeared to involve an older woman. The deejay (who was 32 years old at the time, Harry was 17) hit it off with Styles after she grilled One Direction for Manchester-based radio station Key 103.

Things got hot and heavy with these two, but Horobin was reportedly married at the time and the reported fling with Harry didn't last.

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2. Caroline Flack: Things continued to stay juicy when the hunky teen linked up with another older woman, 32-year-old Flack. Their 14-year age gap stirred quite a bit of cougar controversy, but Flack didn't let that (or the threats from fans) get to her.

"We weren't bothered and his family wasn't bothered. But the thing about unconventional relationships is that other people do seem to be bothered," she reportedly told Glamour magazine. "I mean, look, it was just really fun to hang out… I don't think we were ever going to have a long-term future. It was fun and it was hurting nobody… [Breaking up] was fine. And now we're friends."

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3. Emma Ostilly: The singer was seen canoodling with the model (who is in his age range) in New Zealand. The two reportedly met on the set of the music-video shoot for One Direction's hit "Gotta Be You," but reconnected when the band traveled to New Zealand, where Ostilly is said to live.

Fans began to go after the then-18-year-old online which caused Ostilly to vanish from social media.

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4. Emily Atack: Harry and the actress enjoyed a brief romance but their love affair was cut short because of the band's three-month-long, 62-date United States tour. 

She recently told Reveal magazine, "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."

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5. Caggie Dunlop: The former Made in Chelsea star and Styles hung out for a bit in July 2012. Dunlop would openly ask Harry on Twitter if he wanted to go over to her place, and even once tweeted, "I love harry styles."

A source close to Caggie told the Sunday Mirror, "She and Harry have been in touch for around a year, but they first kissed about nine months ago...They are both young and attractive and they really enjoy each other's company. There's great chemistry between them. They are definitely planning to see a lot more of each other over the next few weeks."

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6. Lily Halpern: The couple sparked rumors of a romance after both were spotted together in New York City, where the 19-year-old Halpern, a singer who's opened for bands like Big Time Rush, was seen leaving the 18-year-old One Direction heartthrob's hotel.

"He's adorable" and "a very good friend," Halpern coyly told E! News, adding, "Who wouldn't have a crush on him?"

7. Taylor Swift: We all remember this pairing, right? The talked-about couple first became public in December 2012 after they were spotted hanging out together at the Central Park Zoo in New York City, and social media instantly blew up with pictures of their outing.

The boy bander helped ring in Swift's 23rd birthday, but at one point their romance fizzled. Harry broke his silence about his split from the country superstar, telling Capital FM, a UK radio station, that he was doing "OK" since the couple called it quits in early January. "Yeah, I'm good," he said.

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8. Kimberly Stewart: Going back to his cougar roots, Harry began romancing Rod Stewart's 33-year-old daughter. "They were introduced by a mutual friend who set them up," an insider told E! News. 'Kim is very strong-willed, she goes for what she wants and Harry appreciates that. It is a very new thing and we'll see where it goes."

Styles even joined Stewart and her family for dinner at Dan Tana's in West Hollywood.


9. Kara Rose Marshall: A couple months after being out with Stewart, the young cutie was caught hanging out with the blond beauty. Harry and Kara were seen with Styles' hairdresser, Lou Teasdale, at the Apple store in New York City, before spending part of their Sunday night on a rooftop together with friends.

Additionally, they were each photographed wearing an identical tour T-Shirt of The Who, which seems to indicate that either Harry and Kara both love the shirt (or the band) and happened to have matching ones or that Styles perhaps offered Marshall a loan of the shirt straight off his back.

Dimitrios Kambouris/Getty Images

10. Cara Delevingne: What was really going on with this pretty pair is a bit up in the air. After spending some time together, E! News learned that Styles was eyeing the runway model for a while. "Harry's been chasing Cara nonstop. He really likes her and has been saying that he wants to be exclusive with her," a source told us.

However, when Harry was asked by one of the news presenters at Burberry Fashion show, "Are you looking forward to seeing your girl Cara walking down the runway?" the boy bander quickly retorted, "She's not my girl! I know what you're doing."

Either way, he was front row, center.