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Jake Gyllenhaal apparently broke Taylor Swift's heart so much because she gave him his virginity, and he didn't show up for her 21st birthday party. She apparently sobbed like there's no tomorrow. According to RadarOnline:
Taylor thought maybe he was planning some sort of surprise. Nope. He didn’t show up and she locked herself in the bathroom and cried the entire night.

“The song that specifically references this ‘event’ is ‘The Moment I Knew.’ They lyrics are all about her birthday party and Jake not showing up.”

The source tells Radar that Swift is still “stuck” on Gyllenhaal and says the relationship left her “damaged goods.”