Jokerry Man — November 28, 2015 in Entertainment 10 Hottest Celebrities Who Lost Her Virginity To Other Celebrities 53 Likes Comment Share #6. Kirsten Dunst and Jake Gyllenhaal Kirsten Dunst lost her virginity in 2001 with Jake Gyllenhaal, when she began her twenties. (Image Credit) Pages: 1 2 3 4 5 6 7 8 9 10 Celebrities Virginity Lost Celebrities Who Lost Her Virginity To Other Celebrities female Celebrities Virginity Lost hot female Celebrities Virginity Lost story of Celebrities Who Lost Her Virginity To Other Celebrities