The police and the community have been long engaged in an ever-evolving dichotomous relationship. This relationship has been strained over the recent decade by police brutality, media coverage of police misconduct, and the increased call for police transparency. Both parties in this disparaging dynamic see the need for improved engagement and communication efforts. This research studied the underlying perceptions, assumptions, and expectations of the police and police training within four demographically diverse neighborhoods in upstate New York. This interpretive phenomenological study focused on the importance of lived experience and experiential learning in creating expectations and assumptions. Twenty-four participants total were sampled in this research. Through semi-structured interviews and focus groups of twelve police officers and twelve community members, three research questions were explored. First, what was the perceived role of the police in society? Secondly, what lived experiences brough the respondents to these expected roles of the police? Lastly, what type of changes can be made in police training and community learning to improve the police/community relationship? Using thematic networking and vignette sampling, multiple findings were identified, and four analytic categories were synthesized. The analysis showed that policing expectations and assumptions are based on lived experiences, childhood presumptions, and cultural norms. Secondly, the lived phenomenon of policing varies based on the socio-economic, cultural, and community settings. Thirdly, transformational critical incidents play a significant role in the creation of assumptions and expectations. Finally, the study showed a dichotomous relationship between the police and the community on ways to improve police training and the policing culture. In conclusion, this study offered various recommendations for both the police population and the community population in steps to improve the community/police dynamic. These recommendations included the creation of a measurable instrument for gauging public perception/approval, increased educational requirements for police officers prior to employment, consideration of an over-reliance on evidence-based tactics, emphasis in police training on the importance of experiential and transformational learning, and the adoption of a more holistic moniker for the policing culture. Community recommendations included the creation of co-learning environments, embracing police engagement over interaction, and emphasis on leveraging the power of lived experience and community-based learning.