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Beware of the serial dater: Jake Gyllenhaal

Deirdre still can't believe SheKnows pays her to do what she loves. She began telling stories before she could even write. Once someone gave her a pen, there was no prying it away; so a degree in journalism was the only thing that made s...

Is Jake a heartbreaker or just unlucky in love?

Oh, Jake! We can't quit him. But, maybe we should? While no one skips between relationships as fast as his ex, T-Swift, Gyllenhaal sure has been around the block a few times before. If you're considering him for your Valentine, consider long and hard.
Taylor Swift

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

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 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 Portma

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

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

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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On the upside, Jake certainly doesn't have a type. He's shared women with both our other serial dating boys, John Mayer (Taylor Swift) and Ryan Gosling (Olivia Wilde). But, what do you think? Would you still date him? Yeah... us, too.
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More serial daters

Beware of the serial dater: John Mayer
Beware of the serial dater: Ryan Gosling
Taylor Swift's boyfriend shuffle

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