Dated for the first time: November 2013 - March 2014
Dated for the second time: November 2015 - February 2016
Jenner and Styles met in November 8, 2012, at X Factor USA backstage. Harry followed Kendall on Instagram in May 2013 but the pair only got closer in November 2013. They were spotted leaving a restaurant on November 20, 2013, and later Styles was papped arriving at Jenner's hotel in London. They were also spotted leaving a hotel in NYC. In January 2014, they were seen cozy at an Eagles's concert. However, by March 2014, it seems that they have ended their 4-month-old fling. Styles and Jenner kept a friendship after their fling, they were seen at British Fashion Awards backstage in December 2014, and they were even hanging out with Jenner's BFF (and also Styles's rumoured ex-girlfriend) Cara Delevingne in January 2015. As of October 10, 2015, Kendall (and Cara Delevingne) were spotted at One Direction's concert in Birmingham, and so started rumors about them being together for the second time. Harry and Kendall were also seen together at AMAs backstage on November 22, 2015. We only found out that they were in fact together again by late December 2015, when the pair went to a yatch trip with Harry's family and Kendall's mother Kris Jenner (along with other people such as friends and even Ellen DeGeneres with her spouse). They were spotted kissing and making out at the yatch in St. Barths during the New Year's Eve.
After the magic holiday together, Jenner and Styles attended Jeff Azoff's birthday party with friends in January 2016. In February 2016, rumors about their second split began, although they kept liking each other's posts on social media and they were even spotted shopping together in LA in April 2016, that was the last time "Hendall" were seen together in a long time. Quickly after being spotted with Harry in LA, Kendall reportedly began dating basketball player Jordan Clarkson. However, it seems that Harry and Kendall remain as friends again since they were seen together in LA with a few friends during September 2016, and Harry attended Kendall's 21st birthday party in November 2016. As of January 2017, the pair attended the same Kings of Leon concert but according to people, they didn't talked to each other.