The success of the Agile Development Methodologies largely lies on its driver, humans. The pair programming which is thepopular unorthodox programming practice, continues to establish itself and being the emerging topic in the softwarecommunity. Along with its well published benefits, there appears to be a room for improvement. A field survey with a groupof experienced professional pair programmers was undertaken. The survey result generated an array of vivid first-hand pairprogramming encounters that are uncommonly found in many pre-designed lab-controlled empirical studies. The surveyresult points to the personality variable as the most influencing variable, and also raised few questions on today’s pairprogramming management and environment. Through the Myers-Briggs Type Indicator (MBTI) and Big-Five Model ofpersonality profile assessments, the role and impact of personality variable is presented and discussed with the respect to thepair programming and other similar dyad team collaboration environments with cognitively conflicting tasks. This effort tobetter manage the pair programming session and optimize the pair programming environment to high fidelity, and othersignificant agile methodologies studies must continue in order to sustain and embrace the values of Agile Manifesto.