Who did Taylor Swift lose her virginity to? Tue-18-Feb-14 10:19 Share this By Jay-Jay FeeneyThe goss is out about who Taylor Swift lost her virginity to! Supposedly it was Jake Gyllenhaal and she was heartbroken when he bailed on her 21st birthday party. Taylor had been “saving herself for marriage” but Jake convinced her to go all the way after 3 months of dating.And when he didn’t show up for her birthday party, she locked herself in the bathroom, crying all night.Then she wrote the RED album!“The song that specifically references this ‘event’ is ‘The Moment I Knew.’ The lyrics are all about her birthday party and Jake not showing up.”Some of the lyrics for the song include, “You should’ve been there, Should’ve burst through the door. You said you’d be here.”“What do you say, When tears are streaming down your face, In front of everyone you know?” A friend says Taylor is still “stuck” on Jake Gyllenhaal and the relationship left her “damaged goods.” You May Also Like Taylor Swift surprises a fan at her bridal shower Taylor Swift melts hearts James Franco laughs off Instagram controversy in Saturday Night Live skit Become a fan of The Edge on Facebook and on Twitter .