Humans require sufficient social understanding and connectedness to thrive (Baumeister & Leary, 1995). The current study evaluates the effectiveness of the Social Intelligence Institute's training program pilot. At a middle school in Phoenix, Arizona, students in a 7th and 8th grade class participated in this pilot program during the spring of 2013. Pre- and post-test questionnaires administered indicated changes in participants reported measures of Perspective Taking, Empathetic Concern, Interpersonal Expectations, and Relationship Self-Efficacy. The program consists of seven modules, each with several sessions, including instructional videos with reflection questions and class discussions. It was predicted that there would be a significant increase in mean scores for the dependent variables in the questionnaire mentioned above from the pre-test to the post-test. However, the null hypotheses were not rejected; statistical significance in t-tests of the measured variables were not met. Yet, the program was more effective for 8th graders than for 7th graders for Perspective Taking. This study of the SI pilot program demonstrates areas of improvement and provides support for wider implementation in the future.