Well-being and flourishing are widely discoursed topics across the globe. The concepts capture their essence from the varied nuances an individual’s psycho-social context and a community’s socio-cultural context. Literature has equated flourishing with happiness and then to the ‘good life’ put forth by Aristotle, something manifested in good things and benefits that lead to flourishing. Flourishing, hence, related to positive psychology and well-being is worthy to be discussed in the context of human growth and development. Social capital has been discussed as a prerequisite for well-being and social performance outcomes. Social bonds, individual autonomy and sustainable choices are among the essential elements that imply collective flourishing. Considering collective flourishing as a more holistic framework, it is intrinsic to the individual emotional well-being that can be attributed to positive self-concept, professional advancements, livelihood accomplishments and positive experiences in the social context. This chapter deals with the nuances of flourishing perceived, experienced and interpreted among the lives of Transgender individuals in the state of Kerala. This discussion is to be reflected and understood in the background of the socio-cultural context of Transgender individuals living in Kerala. The social structure and practices of Transgender community in Kerala have a profound influence on understanding the concept of ‘flourishing’. Unlike the Transgender community in other states of India, the TG community in Kerala has distinct features that stand in the way of collective flourishing. Nevertheless, there are positive factors of individual well-being and flourishing that ultimately permeate to achieve a prosperous and resilient society.