Thursday, Aug 27, 2020, 9:10 pm

By:Mike Litzler

#3 Jake Gyllenhaal

Jake Gyllenhaal and Taylor Swift's relationship is a great example of a whirlwind romance. The pair reportedly dates for only five weeks. It was Gyllenhaal who made the first move by asking his people to introduce him to the singer. A rumor even circulated that he spent $160,000 to have her flown to him on a private jet for a date. Even though they spent Thanksgiving 2010 with his family, things didn't work out. Gyllenhaal gave himself a late birthday gift by breaking up with Swift, via text message, less than two weeks after his December 19 birthday.