Radaronline.com is claiming that Taylor Swift lost her virginity to her then-boyfriend Jake Gyllenhaal when she was 20. She apparently was waiting for marriage, but was convinced after three months of dating the star, who was 33 at the time. Swift thought she was going to marry him and was absolutely crushed when he didn't show up to her 21st birthday party back in December 2010.

Rumor has it that her entire "Red" album was inspired by their break-up! Poor Taylor, but hey, at least she got a #1 album out of it!

Thumbnail Source: Getty Images

Album Source: Big Machine