Abstract: A computerized system and method of teaching vocabulary to a student includes an application that provides predetermined word lists. A teacher or instructor may also add words to the word database based on a user's curriculum, cross-curriculum or words of interest. The words in the word database are utilized to automatically create an individualized vocabulary assignment. The user is instructed to learn the new vocabulary words by breaking the words into their suffixes, prefixes, roots and word origin and history. The student is encouraged to create a word history or etymology of the word to understand the history, the language of origin, and the language from which the word is borrowed. The student is then instructed to use the vocabulary word(s) in a sentence. The teacher, instructor or an online tutor monitors the completion of the various assignments by the student and also monitors how well the assignments are performed.