The present descriptive survey aimed to identify the obstacles to building and maintaining relationships in the teaching-learning process from the viewpoint of high school teachers and students in Isfahan. The statistical population of the study comprised all high school teachers and students in Isfahan (8097 and 140250 individuals, respectively). Cluster sampling method as well as random stratified sampling method were used and through taking into account the dropout rate, the sample size was determined to be 110 and 240, respectively. The instrument consisted of a self-devised questionnaire with 21 close-ended items and one open-ended item. The content validity of the instrument was confirmed by specialists and its construct validity was examined. Cronbach's alpha coefficients obtained for the reliability of “Teachers” and “Students” Questionnaires were 0.98 and 0.97, respectively. Results revealed that from the viewpoint of teachers and students the extent of obstacles to establishing relationships was higher than the theoretical average. Teachers attributed the most prevalent obstacles to building positive relations to teachers’ boredom in classroom, contradiction between teachers’ speeches and actions, and making students hopeless about pursuing their education. According to the students, the most common barriers to establishing relationships are teacher favoritism and teachers’ inappropriate reaction to students with achievement and discipline problems. Furthermore, there was a significant difference between students’ and teachers’ viewpoints on the obstacles.