Jake Gyllenhaal and Reese Witherspoon
When she met Jake Gyllenhaal on the set of Rendition in 2007, she became friends with him and later began dating him. It was clear that the two charming actors had a special connection even though they never featured onscreen together throughout the numerous behind-the-scenes scenes that were filmed.
Given their history of meeting and falling in love on set, it was only right that these two should discover love on set as well. Unfortunately, after two years of dating, the couple decided to call it quits in 2009.