This article analyzes and compares the use of the famous sign of "a virgin is pregnant and she will bear a son" in Isaiah, the Septuagint and the Gospel of Matthew. The article investigates the two words-the Hebrew עלמה (marriageable young woman) and the Greek Παρθ’єνος (virgin). It attempts to explain the goal of using these words and interpret the texts according to the different narratives, religious backgrounds, and beliefs of the authors. Women in the ancient world stood in a paradoxical position. The culture of praising virginity is a sign of unfairness with regard to gender. Christianity should rethink how "the virgin is pregnant" should be re-interpreted in our contemporary world.