This paper assessed the emotional and cognitive decision-making process regarding a hypothetical unplanned pregnancy in a convenience sample of female adolescents (N = 85; mean age 16.8), throughout an electronic role playing simulation. This work aimed at: describing adolescent’s emotional reactions and cognitive responses to an unplanned pregnancy; identifying personal attitudes toward parenthood; evaluating the role played by adolescents’ personal attitudes toward parenthood and positive and negative attitudes toward continuing the pregnancy or having an abortion in predicting the final choice (keeping the baby vs. having an abortion). Findings highlighted the presence of three main attitudes toward parenthood (parenthood idealization, rejection of commitment, adolescents’ expectations toward the partner) and the importance played by them together with negative attitudes toward continuing the pregnancy and having an abortion in guiding the adolescents’ decision-making process.