The 12th century was a controversial period of deepening ecclesiastical influence on all strata of the population, strengthening church prohibitions, expansion of convents; the century of establishing a new stratum of intellectuals, the first rise of women role in society and the formation of the courtly culture’s foundations. Philosopher Peter Abelard and his student Heloise were chosen for examination by us as the bright personalities of the 12th century, a product of medieval society and the voices of their time. An exceptional historical case of well-documented reliable information on the personal relationship allows us to correlate the world-view of lovers and their lives with the socio-cultural realities of High Middle Ages. The aim of the article is a historical analysis of the relationship between the philosopher-teacher Abelard and the student Eloise in the socio-cultural context of the 12th century. In previous studies scholars have only indirectly touched certain aspects of the teacher-student relationship in the context of intimate gender relations of the High Middle Ages. We analysed the autobiography of Peter Abelard, the letters of Abelard’s contemporaries, his correspondence with Eloise. We arranged scientific achievements of historians and examined personal life of the couple against the background: tactics of seduction, intimacy, determining and understanding the relationship status, men’s standing in society after castration. Emphasis is placed on the progress of 12th century’s social consciousness in the light of the personalities’ world-view analysis. A division between individual views and the Catholic medieval outlook is analysed. Through the study of the transformation of the relationship between teacher and student, and future lovers, we have shown that the views of Eloise and Abelard illustrate a feasible range of medieval perceptions of the relationship, in tune with the new era challenges, yet integral to its time.