Taylor about writing "I wish you would", keep in mind that Harry bought a house just one street down from hers back in Jan 2013 after their breakup.
*somewhere around 2014* Taylor introduces steal my girl on the radio
Somewhere around 2017
Cameron Crowe (the guy who interviewed him for the magazine) said harry needed a break from the interview after Taylor's name got mentioned, he said he took a long time to adjust and come back to answer a few questions about her/their relationship.
and by that interview/the album, it's pretty obvious they had an on & off relationship for 5 years, with the last song about the relationship being in hs1 til 2017, it could've been his 1989 but we may never know that for sure.
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Haylor Timeline
RomanceHarry Styles and Taylor swift relationship timeline (Active and still adding stuff) (Half creds to haylortml on twitter) Enjoy♡︎ Highest rank: #1 on tarry