Taylor Swift, Nicole Scherzinger, Olivia Wilde: A look at Harry Styles' dating history

Styles was 17 when he fell for Caroline Flack who was 31 at that time. The two met on the sets of 'The Xtra Factor'. Flack had even mentioned in her autobiography that how Styles admitted to his feelings in various interviews and to his friends. The two reportedly dated for a few months in 2011 and ended it in Januray 2012 when Flack started getting threat messages from Styles' fans. Years later, Styles wore a black remembrance ribbon at the 2020 BRIT awards, held just days after Flack's death.

Styles was also linked to radio host Lucy Horbin. Horbin's husban had spoken of the 'betrayal'during an interview to The Mirror. He had revealed that the relationship was in trouble and Horbin's affair with Styles was the final nail in the coffin. 

Harry Styles and Taylor Swift's releationship dominated gossip coloums nearly entire of 2012. The two were introduced by Justin Bieber in March 2012 Kids' Choice Awards. Styles was 18, Swift 22 and the two were clicked together at Central Park. Both expressed through music and spoke about how its difficult to date amid constant public and media glare. The two broke up in 2013 and they even wrote songs dedicated to each other. 

In late 2013, Styles had a 'fling' with Pussycat Dolls singer Nicole Scherzinger, who was 16 years his senior. Scherzinger had been a guest judge on the 'X-Factor' in 2010 when One Direction was formed.

Styles and Jenner got close to each other in late 2013 but they never made their relationship official as Styles also was spotted with various Victoria's Secret models. The two again became the talk of the town when Styles spent 2016 New Years with Jenner. A week later, Jenner's sister Khloe Kardashian said she thought they were dating. "Do I think they’re dating? Yes," she told ET. The two moved on by mid-2016 but remained friends. 

Styles next had a year-long relationship with Victoria's Secret model Camille Rowe, 30, who is seemingly the inspiration behind his 2019 album 'Fine Line' even though he hasn't openly admitted to that fact. 

Sources close to Styles and Wilde state that the two have started going out only a few weeks back and that they are enjoying each other's company. Wilde's past relationship with Jason Sudeikis was a well known fact while Styles barely speaks out about his relationships.