American culture is greatly influenced by conservative and religious views that construct adolescent sexuality as problematic. Consequently, American teenagers are often informed that abstinence is the right moral choice and will allow them to lead a successful adult life. The ultimate punishment for engaging in pre-marital sex is deemed to be teenage pregnancy. This is evident in the way that the adolescent mother is constructed as a deviant citizen who drains the government of welfare payments, rejects family values, and defies the rigid path to economic success advocated by capitalist ideology. Young Adult literature reflects and communicates such dominant societal attitudes to young readers. In this article, four Young Adult novels were selected to see whether negative attitudes towards teenage sexuality and pregnancy were replicated in the narratives. The two novels from the mid-twentieth century, "Two and the Town" (Charles Scribner's Sons, New York, 1952) and "My Darling, My Hamburger" (HarperCollins Publishers, New York, 1969), reinforced contemporaneous attitudes by presenting adolescent sexuality as wayward and thus punishable with the shame of enforced marriage or illegal abortion. To examine whether such conservatism still exists in the twenty-first century, two contemporary novels, "Jumping Off Swings" (Candlewick Press, Somerville, MA, 2011) and "Me, Him, Them and It" (Bloomsbury, New York, NY, 2013), were selected for comparison. These novels contain similar messages since casual sex only led to shame for the female protagonists and the penalty for their recklessness was pregnancy. The novels, regardless of period, reinforce conservative messages that tell adolescents to be wary of their sexual urges, to abstain from sex, and to view teenage motherhood as deviant.