41.Reese Witherspoon and Jake Gyllenhaal

Though the world is busy with the boom of technology, everyone was shocked when Reese Witherspoon and Ryan Phillippe announced their separation in 2007. While most Ryan-Reese fans can’t get over their split, it was a surprise to everyone when Jake Gyllenhaal became her new beau.

The actors met while filming Rendition in 2007. Though the two knew each other through Phillippe since Gyllenhaal was his gym pal, Witherspoon started seeing him in a new light. Admittedly, she developed a little crush on him as they get to know each other, and the two soon became a couple. Apparently, their relationship was put on hold as she was still dealing with her lawyers regarding her separation. In 2008, Gyllenhaal and Witherspoon got back together and made their relationship known to the public. They broke up in 2009 as the actress was not ready to remarry. Despite everything, Gyllenhaal holds no grudge against her and still praises her whenever there is an opportunity.