Taylor Swift
This was doomed from the start, which is probably why they only lasted about three months. Jake's not old, but Taylor is young... and not even mature for her age. She wasn't his princess. Thank God.
Olivia Wilde
This may have just been a fling. While visiting Chateau Marmont in June of 2011, Jake was seen getting grabby with Wilde, who has also dated fellow serial dater, Ryan Gosling.
Reese Witherspoon
Reese and Jake met on the set of Rendition. Jake saw Reese through her divorce and the couple were together for about two years before parting ways.
Natalie Portman
Jake dated the Black Swan beauty for a while in 2006. It couldn't have ended too badly: Jake was incredibly kind about her when he helped award her with the Desert Palm Achievement Award.
Kirsten Dunst
This should have worked out. After all, Kirsten was sister-approved by Maggie Gyllenhaal, who introduced the two. Sadly, they split up after living together and dating for two years.
Jenny Lewis
Jake originally dated the Rilo Kiley singer back in 2001. However, after his split from Taylor Swift, Jenny became his plus-one once again. She even attended the 2011 Golden Globes with him.
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Images courtesy of WENN.com
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