Friends of Taylor Swift can't seem to keep anything private and just dished about who the global superstar lost her virginity to.  Apparently the lucky lad to get the distinct honor was none other than A-list actor Jake Gyllenhaal a few months before her 21st birthday party.  P.S. he was 33 at the time.

To ad insult to injury, apparently shortly after it happened, he seemed to distance himself from Taylor and din't even both to show up at her big 21st birthday party, and she ended up spending the most of the evening locked in the bathroom crying.

According to those same so-called friends, every song on her latest album 'Red' is about Jake and how he did her wrong.  Now its no secret that Taylor likes to dish about her ex's through music, so this doesn't sound far fetched.  We love Taylor and look how she's bounced back.