The Virginity Loss Stories Of 15 Hollywood A-Listers

Jason Segel

Gentlemen, take note. Chicks always go for a guy with an instrument. At the age of seventeen, Segel taught himself to play piano in an effort to pick up some ladies. He then found a less-than-bright young woman and convinced her that he’d written Elton John’s “Your Song” for her before promptly losing his v-card. Nicely done!

Kirsten Dunst

Give the girl a medal for waiting to do it with someone special! Kirsten reportedly lost her virginity to her boyfriend of two years Jake Gyllenhaal. After a very public relationship, the pair split fairly amicably as far as Hollywood break-ups go.

Taylor Swift

Sigh. Oh, T-Swizzle. Whatever will we do with you? Taylor Swift also lost her virginity to Jake Gyllenhaal, though the two barely dated for more than a few months and Taylor had only just finished high school when she began seeing the thirty-something Gyllenhaal. Smooth, guys. Real smooth.