When Manny Papadopoulos, a young aspiring writer, meets Eve Stephanopoulos, the girl of his dreams and a virgin to boot, he fears that getting into a serious relationship will derail him from his dream. Teddy, Manny's best friend, who will do anything to get back together with his ex, Jenny, eases Manny's concerns by pointing out the many pros of the 90s virgin and dismisses Manny's commitment fears by suggesting things can't get serious with a virgin. Eve falls hard for Manny and, misinterpreting his selfish motives, admires his wish to keep the relationship chaste. But things grow complicated as they do for the other young Greek Americans in their circle, including Eve's sister Joanne and Manny's friend Mike, who repeatedly cheats on Joanne.