From that marriage he reportedly ruined in 2011, to the model who couldn’t deal with the wrath of One Direction fans, to dumping Taylor Swift, to “not dumping” Caroline Flack, to two-timing Kendall Jenner, it seems it’s not just his look Harry Styles likes to change up.
Harry Styles keeps his ladies guessing, too. When Taylor Swift said that her number one feeling while dating Harry was “anxiety,” as reported by the Daily Mail, many Harry-lovers chided Swift for attacking their boy. However, looking at Harold’s history you almost start to feel like maybe Taylor has actually done her research.
Every time the One Direction star has ended things with a romantic partner, it has been done in an unexpected fashion, with a lot of panache, and a certain je ne sais quois (incidentally, E! Online attributed this quality to Harry recently when they explained why they think he will become a star).
Those flings never quite know when the H-bomb is going to drop (H in this case is for Harry). Will it be as sudden as the “History” music video drop, or rolled out slowly over a few sensitive phone calls (similar to when 1D trickled those “making of” clips in the days leading up to the “Night Changes” release)? Will Harry be super-gentle like he was when he tweeted “please know I did not ‘dump’ Caroline [Flack]” or keep things edgy, like when he two-timed Kendall with a stylist, leaving her to agonize over whether it was because she had flirted with Cristiano Ronaldo? Will he leave the woman distressed as distressed denim or make her feel as soft and fuzzy as a cashmere sweater?
For evidence of Harry Styles’ bipolar breakup style, let’s take a look at his lucky exes, who can definitely draw solace from the fact that they lived many fangirls’ dream for at least a short time.
For the purposes of this analysis we will not include Harry’s “breakup “with bandmate Louis Tomlinson (super-thorough analyses have already been done and posted all over Tumblr, and the Larry jury is out on whether the rumored gay lovers are estranged or still together).
Caroline Flack: They remained friends despite fan backlash and Harry even defended her on Twitter
Aw! This breakup is sweeter, softer and more attuned to feminine sensibilities than Chanel’s Spring 2016 Couture collection. Harry supported his pal through their three month dating stint, steadfast even in the face of backlash from protective 1D fans, and when he and Caroline broke up he took to Twitter to call her “one of the kindest, sweetest people I know.”
Please know I didn't 'dump' caroline. This was a mutual decision. She is one of the kindest, sweetest people I know. Please respect that.
— Harry Styles. (@Harry_Styles) January 27, 2012
Lucy Horobin: The fling with Harry broke up her marriage
Lucy Horobin’s husband was apparently not too happy about her fling with Harry, and Lucy soon had graver things to worry about than whether the 1D star was still taking her calls, according to Harper’s Bazaar.
Causing somewhat of a scandal, Styles was then linked to married DJ Lucy Horobin in 2011. After it was reported that the two had ended up in bed together, Twitter went into an uproar and Horobin ended up getting a divorce.
— Lucy Horobin (@LucyHorobin) February 2, 2016
Caggie Dunlop: It was fans who did the dirty work
Marie Claire reported that Dunlop was put off by all the attention she received from One Direction fans when she dated Harry Styles.
“It was horrible for Caggie,” close friend Millie Mackintosh told the mag.
‘I’m not going to speak about it, but when people are showing up outside your parent’s house it’s gone too far…’
Apparently “the attention that comes with a One Direction romance can wear thin.”
‘Caggie is a fun loving girl…but it does all get a bit much. There’s a different direction she wanted to go in and I think she got a bit freaked out.’
— Catherine Dunlop (@Caggie_Dunlop) February 3, 2016
Thus, the two parted ways. If Harry had really wanted to stay with Dunlop he would have fought for it, right? It seems in this case the will of Directioners and the will of freedom-loving Harry lined up neatly, and she drifted out of his life.
Taylor Swift: Harry just disappeared one night
According to Hollywood Life, Harry was always very attentive and said all the right things while he was with Taylor, but she could not shake a gnawing feeling of anxiety.
“[Harry] was all, like, ‘You’re amazing – I want to be with you. I want to do this [but then he] disappeared one night and after that it was like he just didn’t want to keep going.”
— E! Online (@eonline) February 2, 2016
Kendall Jenner: Harry had a fling with a stylist, said he did not think they were official
This sounds like a simple misunderstanding, but who can say when the deep and mysterious mental machinations of Harry Styles are part of the mix? Harry and Kendall made out on a yacht over New Years. For a few weeks it seemed like they were on, with talk of Harry giving Kendall his t-shirt to sleep in, rumors about Harry appearing on Keeping Up With The Kardashians, and even some talk about the two moving in together. Next thing we knew it was reported that Harry had slept with that stylist in London, and was saying that he and Kendall were “not serious.”
It appears the Jenner sister may have thought otherwise, because outlets are now reporting that she is hurt and feels “like a fool,” according to Sugarscape.
— Seventeen (@seventeen) January 13, 2016
(Photo by Mat Hayward/Getty Images)