It seems that there will be no more fun romps in the cold for Jake Gyllenhaal and Taylor Swift now that the two have decided to break up. But long before Gyllenhaal, 30, and Swift, 21, were dating, he had been attached to some of Hollywood's foremost leading ladies, and a few other singers as well.
Rilo Kiley frontwoman Jenny Lewis and "Donnie Darko" star strummed each other's guitar strings for about a year in 2001. Then, Gyllenhaal famously dated Kirsten Dunst. The pair got hot and heavy in 2002 and quickly became a red-carpet staple, but Gyllenhaal always seemed to keep things in perspective. "Kirsten and I know what's real and what isn't," he told People at the time. "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. 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. Their romance was filled with coffee shops and snuggles, but hot lattes weren't enough to keep the sparks going, and it was announced this week that they had broken up right before the New Year.