Title: A Full Rundown of Taylor Swift's Hollywood Dating History
Headings: A Full Rundown of Taylor Swift's Hollywood Dating History
A Full Rundown of Taylor Swift's Hollywood Dating History
A Full Rundown of Taylor Swift's Hollywood Dating History

Content: From Jake Gyllenhaal to John Mayer, see every heartthrob who has been lucky enough to romance Taylor! Previous Slide
Next Slide
17 things you probably didn't know about 'The Handmaid's Tale'. INSIDER
Full screen
1/11 SLIDES © Getty / Jackson Lee
A Full Rundown of Taylor Swift's Hollywood Dating History
We imagine that one of the benefits of being a massively successful pop star is that instead of having to agree to go on an awkward date with Ted from Accounting, you have a whole buffet of Hollywood's hottest bachelors at your disposal. If anyone is a good example of this, it's Taylor Swift. The 31-year-old "Cardigan" singer has been linked to musicians and movie stars alike and has a penchant for memorializing her fallen relationships in song. From Jake Gyllenhaal to John Mayer, see every heartthrob who has been lucky enough to romance Taylor! Microsoft and partners may be compensated if you purchase something through recommended links in this article. 2/11 SLIDES © Getty / Jeff Kravitz
Joe Jonas
When: July 2008 - October 2008
Taylor's first highly publicized relationship was with Jonas Brothers singer Joe Jonas. The pair dated for a few months before Taylor famously told Ellen DeGeneres that he broke up with her over a 27-second phone call.