18. Matthew Fox

Known as the studly Jack Shepard on Lost, Matthew Fox’s first time was equally bewildering as his time on the island. According to Fox, he was 12 years old at the time. Although it wasn’t the girl’s first time, Fox recalls very much being an awkward virgin. The memory isn’t as fond as Fox anticipated it would be. He described the image, stating: “It happened literally on the ground by a river while a rodeo was going on in town. It was absolutely terrible and awkward – just two f*cking kids lying down and pulling our pants down.”