This thesis is in two parts. The first part consists of translations of five medieval commentaries on the Book of Lamentations composed by Rashi, Yosef Kara, and Abraham ibn Ezra. While the Rashi and ibn Ezra commentaries are available in translation, the two written by Yosef Kara are not. These two Kara commentaries contain transliterated Medieval French dialects that are difficult to translate, at least in part, because the copyists did not appear to understand what they were copying. The translation of these texts has, therefore, begun the long task of trying to develop a system by which Kara's Medieval French explanations may be understood. The initial findings are recorded in the translations. The second part of this work concerns the development of a method by which these translations may be better understood. A comparison of eight verses from the Book of Lamentations was made, and a method based on sociolinguistic and literary theory was applied, to attempt an explanation of the use of peshat method of exegesis as a function of meaning.