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.
Images courtesy of

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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Comments on "Beware of the serial dater: Jake Gyllenhaal"

Neferti February 02, 2014 | 2:15 PM

Meeting the fam after the second date.. no! My bf didn't meet the fam till about 6months later. I dont just bring anyone around my family. But that's just me...

Tina February 24, 2013 | 4:59 PM

So he's dated about 6 girls in more than 10 years? Big deal.

Tracey February 03, 2013 | 4:48 PM

He needs to be, or at least find a young lady that is GROUNDED; not flighty like himself; Best compatabilities for Sagittarians'; Aries, Libra, Leo, and some Geminis'.

Mia February 01, 2013 | 5:51 AM

Hmmm I see what you mean, but hey- guys like him couldn't care less about their relationships! At the end of the day, he's got a tough choice.... There are billions of girls out there who want him; all he has to do is pick one! ;)

Oh Tina February 01, 2013 | 5:20 AM

Ryan Gosling is also not a serial dater, yes jealous much again. Two of the hottest guys in Hollywood are labeled serial daters because the writer can't have him. A good way to get over deseperation and depression is to trash guys you can't have with labels that are bull.

OH Tina February 01, 2013 | 5:17 AM

Please get over it, Jake dated Taylor Swift for real. As far as being a serial dater, he was with 2 women for over 8 years. As for Jenny Lewis, they dated in their teen years and she was his friend date at the Globes. And the other women much like Taylor's "boyfriends" were casual. And for the record he also dates "normal" girls because yes he dates, jealous much? You should be Diedre, he will never date your ass.

Tina February 01, 2013 | 4:54 AM

Jake Gyllenhaal is and nice - ideal fake boyfriend for getting publicity! (No, Taylor Swift is not the only one who uses fake boyfriends for making money.)

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