Jake Gyllenhaal has been lucky with the ladies in Hollywood. Take a look back at some of his past high-profile flames, including Kirsten Dunst, Natalie Portman, Taylor Swift, and his current girlfriend Alyssa Miller.
Witherspoon -- who first began romancing Gyllenhaal while shooting Rendition -- "broke his heart" when she ended their three-year courtship in December 2009. "No one cheated," a source told Us. "There was no drama."