In the rabbinical literature of the Talmudic era, one can see that various words were not used only according to their ordinary meanings, but also with additional, connotative, and symbolic meanings which are not found in dictionaries. However, these meanings were well known to the sages of that period. For example, the word “Pundak” in Hebrew means “inn”. An inn is understood as a dubious, vicious place, convenient for committing sin. The atmosphere in such place may prompt pagans to commit the sin of bestiality. In the rabbinic literature there is an alternative concept for designating a place where a visitor can spend the night: this is “beit midrash” – a room where religious Jews study traditional literature. Decent people would stay for a night in a beit midrash. An additional example is the topic of сaptives and their ransom. A large number of Jews were captured by the Roman Empire after the destruction of the Second Temple. Many prisoners were women, who were sent to Roman brothels. The Jewish community made great efforts to redeem these women. However, some of them did not want to return to their people, since they had already re-built their lives with Roman men. These women, upon returning to the Jewish community, brought with them foreign customs such as idolatry and witchcraft. Other words in the rabbinical literature also have additional connotations. For example, “talmidim”  which the dictionary translates as “students”, also has the connotation of “ignorant, unlearned people”; “tava” translated as “(he) required” can have the connotation of “(he) sexually harassed”; “ilan” given as “tree” in the dictionary can have the connotation of “tempting, alluring object”. There are many other examples of words with additional meanings. One could even write a dictionary of the connotations of words in the rabbinical literature. This article provides a first opportunity to learn the connotative meanings of words in the rabbinical literature.