Taylor Swift & Jake Gyllenhaal

Of all the many guys Taylor Swift dated, Jake Gyllenhaal stands out. We’re not sure why, though. Maybe it’s because of their nine-year age difference, or just for the reason that he’s an A-list actor. Anyway, the two dated from October 2010 to March 2011, when the singer-songwriter was 21 years old and the actor was 30.

Swift’s 2012 album titled Red was released a year after she broke up with Gyllenhaal. Of course, the audience was quick to speculate that she channeled her heartbreak into her new album. According to reports, the actor called off their romance because he struggled with so much publicity. The two eventually moved on and dated other personalities. Even though they broke up years ago, their relationship has lived on through Swift’s music. Well, at least she’s still earning some investment money from her heartaches.