En 2002, il a fait ses débuts au théâtre, dans la pièce londonienne de Kenneth Lonergan, This Is Our Youth qui enthousiasme également les critiques.
Et en 2003, il partage l'affiche du film indépendant Good Girl de Miguel Arteta, où il donne la réplique à la star Jennifer Aniston.
See, America's flirt had previously decided to save her sacred flower for her honeymoon — awww, so pure!!!
— but her relationship with Jake was going so gosh-darned well that decided there was no reason to wait! Shortly after they, uhh, baked their first love custard, though, he turned into a different dude!
According to sources who are close to the 24-year-old starlet, Jake & Tay Tay's relationship went downhill about the time she gifted him her virginity!
While he didn't disclose which relationships they were, he had long-term romances with Dunst and Witherspoon.
He and Dunst met in September 2002 and announced their split in July 2004. And last year, Gyllenhaal and model Alyssa Miller split after about a year as a couple.
“She thought she was going to marry Jake, that’s how in love she was with him,” the source told Radar.
PHOTOS: Taylor Swift’s Birthday Garden Party But shortly after the two began sleeping together, Swift threw a 21st birthday party for herself in Dec. and Gyllenhaal was expected to fly in for the bash the source claims — but he was a no-show, leaving the “Our Song” singer devastated. “Taylor thought maybe he was planning some sort of surprise. He didn’t show up and she locked herself in the bathroom and cried the entire night.” And as Swift is known to do, the country starlet penned nearly an entire album about her heartbreak over Gyllenhaal.