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It’s easy to think that Harry Styles has lived more than 22 years already, after coming to fame in One Direction and seeing that band dissolve. The fact that he has been linked to so many different women makes it seem like he’s been around longer than he has. Harry has been a busy boy, making us wonder how he found the time for all that dating around. Here are all the lucky ladies who have supposedly had their time in the sun with the singing star.

1. Abigail Crawshaw

Abigail Crawshaw and Harry dated at the ripe old age of 12, which mostly meant eating lasagna together. It was only puppy love, but they once reunited backstage at a One Direction show to take some cute photos.

abigail crawshaw

2. Felicity Skinner

Felicity Skinner was reportedly Harry’s “real” first girlfriend, and the two started dating in their earlier teen years. She has said: “We were together for just under a year. We started seeing each other when we were both about 15. He was really sweet. He was a really good boyfriend, very romantic and, yes, shy.” Aww. That shyness didn’t seem to last long.

felicity skinner

3. Caroline Flack

Next up was the X Factor host Caroline Flack, who is a whopping 14 years older than Harry. He was 17 when the two started dating. “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.” No harm no foul.

Caroline Flack
Featureflash Photo Agency /

4. Cara DeLevingne

Harry and supermodel Cara DeLevingne sent tongues wagging in 2012 when the singer started to show up at her runway shows…a lot. The 1D singer was frequently seen sitting front row in support of her. When asked about their dating life Cara simply responded with: “I like to keep my private life private and that’s all I’m going to say.”

Cara DeLevingne and Harry Styles

5. Alexa Chung

Alexa Chung adamantly denied that she and Harry had a thing, but they were caught spending some quality time together on Valentine’s Day, which is a little suspicious. Once the paparazzi caught up with them she tweeted a solid enough denial. “I AM NOT DATING @Harry_Styles! Ps Sorry @Harry_Styles, fancy a date?”

Alexa Chung
Featureflash Photo Agency /

6. Millie Brady

Harry was dating British model Millie Brady for a bit, but ended that with a simple no-show. A source said: “It was nothing personal – he just wants to keep things casual with Millie at the moment. He had messaged saying he would meet her, then he didn’t show. Millie did feel a bit let down. I know she was very much looking forward to meeting him again. But it’s not going to work out between them any time soon.”

Millie Brady
Helga Esteb /

7. Taylor Swift

Taylor Swift and Harry Styles had an official thing happening back in 2012 and 2013, and in true Taylor fashion she documented the experience by writing music about their relationship. Both “Out of the Woods” and “Style” are apparently about Harry. So how does he feel about that? “She’s really good, so…they’re good songs. So I’m really lucky in that sense.” Any man has to know by now that getting involved with Taylor will be followed by some not-so-subtle lyricism.

Taylor Swift Harry Styles

8. Kimberly Stewart

In 2013 Harry was linked with Kimberly Stewart, who is another lovely lady 14 years his senior. Kim’s dad Rod Stewart even confirmed the relationship, and sang his praises about the guy to boot. “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…Bo*****s, I’ve let the cat out of the bag. Harry couldn’t be a kinder. He is very funny guy.”

Kimberly Stewart and Harry Styles

9. Daisy Lowe

Harry and model Daisy Lowe were linked after being spotted together a few times, however this was never exactly confirmed. One might think it wasn’t likely since Daisy is friend’s with Alexa Chung, who also supposedly dated him. Although, who knows, because…

Daisy Lowe
Featureflash Photo Agency /

10. Kendall Jenner

Kendall Jenner is one of the models in Taylor Swift’s strong girl squad, but it seems as though both of the ladies have spent some time with Harry. Kendall has claimed that the two were just friends, but then they were photographed cuddling on a luxury yacht in St. Barts with both of their parents along for the ride. Yes, all the moms have met.

Kendall Jenner Harry Styles

11. Erin Foster

Erin Foster is a socialite best known for her mockumentary show Barely Famous, but many people don’t know that she and her sister are half sisters with Gigi and Bella Hadid. Well supposedly she and her 12 year age advantage had a thing with Harry as well. But there aren’t any pics to prove it.

Erin Foster
Tinseltown /

12. Paige Reifler

Model Paige Reifler dated Harry dated in the summer of 2014. This was confirmed with a simple “Yes, I am seeing him.” Can’t really debate that one. “I went to the Warner party at Shoreditch House with a friend and saw him there. The next morning I woke up and I was in all of the newspapers and magazines. I wasn’t expecting that, it’s not like that in New York.”

paige reifler

13. Nadine Leopold

Next was another gorgeous blonde model named Nadine Leopold, who was actually the one who did the dumping in the situation. According to one source: “Nadine wanted a more serious commitment from Harry. She felt like he needed to make more of an effort to see her. She just didn’t feel like he was taking their relationship seriously enough, and basically she doesn’t have time for any games in her life.”

nadine leopold

14. Emma Watson

Emma Watson and Harry Styles were first spotted together at a soccer game, after he had presented her with an award for her gender equality foundation He For She. Emma seemed smitten when she said: “Harry Styles just said the words, ‘He for She,’ so that’s really cool.” Sources claim the two were trying to avoid photos when they were on their soccer outing.

Emma Watson Harry Styles

15. Megan Smith

Harry reportedly had a secret fling with private airline hostess Megan Smith, who he met when she was working while the band was on their On the Road tour. Supposedly Harry broke things off as soon as people found out. Megan now claims that Harry cheated on Kendall with her. Oh the drama.

megan smith

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