Harry Styles’ Girlfriends 2020: Who is Harry Dating Now?

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Harry Styles is one scandalous lover. Just as we thought he was getting it on with Kendall Jenner, rumor has it he’s dating the air hostess from his private jet. Megan Smith was serving on the One Direction jet and toured with them for three months during their “On The Road Again” tour. The two bonded in the air, and he even called her his “girlfriend.”

Based on her Instagram, Megan is one hot girl. But where does she place among Harry’s many, many, many ex-girlfriends? (Or *ahem* past conquests.) Let’s take a look.

2011

Caroline Flack

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While they dated in December 2011, she was 32 and he was 17, therefore solidifying our knowledge of Harry’s thing for cougars. Caroline was The X Factor‘s presenter while Harry was auditioning.

2012

Emma Ostilly

Twitter @emmaostilly

In April 2012, she was also rumored to be in a relationship with Harry…again. Except this time there was actual evidence to support that as they were spotted kissing by the paps.

2013

Cara Delevingne

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He sat front row at her fashion shows, sparking romance rumors. It was super cute, actually.

2012-2013

Taylor Swift

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Harry and Taylor infamously dated in late 2012 and early 2013, providing inspiration for several of Taylor’s songs including “Out Of The Woods” and “Style.” However, Harry said that he didn’t mind being the subject of her songs. “She’s really good, so…they’re good songs,” he said. “So I’m really lucky in that sense.”

Haylor. ’nuff said.

2013

Kimberly Stewart

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Harry loves older women! When he was 19, he dated the 14-years-older Kimberly. Her dad, Rod Stewart, confirmed the relationship. “[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…,” he said. “I’ve let the cat out of the bag. Harry couldn’t be kinder. He is very funny guy.”

2014

Paige Reifler

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Harry and Paige, a model, briefly dated in summer 2014. “Yes, I am seeing him,” she said at the time.

2013-2014, 2016

Kendall Jenner

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Harry and Kendall were seen spending a lot of time together in summer 2013 and early 2014. In 2013, Kendall told reporters, “No story, we’re friends. He’s cool.” However, things may have gotten more serious later on.

Fast forward to 2016, and it appears Harry Styles, 22, reportedly has his eyes set on his supermodel ex, Kendall Jenner, 20, following their recent romantic getaway to St. Bart’s. This time, he’s not playing around.

After airing their feelings for each other during their PDA-filled getaway to St. Barts over the New Year’s break, the British singer is ready to give their love another shot, but it’s going to be the real deal. “He’d love to have a proper girlfriend,” a source close to Harry told Us Weekly. “If she’s [Kendall] keen to take it to a serious level, he would be too.”

Too bad Harry and Kendall are already a thing of the past. And Megan Smith had a real short shelf life. The One Direction heartthrob is yet again, on the prowl.

Ladies, you better watch out.