He then moved on to his "Rendition" co-star Reese Witherspoon in 2007.
"Suffice it to say, I'm very happy in life, and I'm very lucky to have a lot of really supportive people around me who care very much for me, and, you know, that's all you can hope for in life," Witherspoon said of dating the actor at the time.
"I am very blessed in that way." After two years, Witherspoon and Gyllenhaal went their separate ways in November 2009.
He and Swift were seen together starting in October 2010.
Turn around means instead of having weekends off you work all weekend and get two week days off.
"We know what happens when you are both actors." In 2004, the actors split, though even years later, Dunst spoke fondly of her former beau.
In 2009, she told Allure, "It would be nice to see him, but we're not good friends." Gyllenhaal followed up his time with Dunst by hooking up with S Club 7 member Rachel Stevens in 2006 (after they had a brief fling in 2001) and Natalie Portman for a short time that same year.
Star magazine reports Jake Gyllenhaal recently went on a date with Natalie Portman and showed up with a dozen pink tulips before they headed to dinner at The Spotted Pig.
This is a huge step up considering his last serious girlfriend was Kirsten Dunst.