The goal of this study was to explore happiness within the context of general personology, which synthesizes theoretical, cultural-phenomenological, and reflective knowledge about personality. Classical and contemporary ideas about happiness have been consolidated and problematized through conceptual questions and answers, the sequence of which reflects the logic of the original integrative approach to understanding individual happiness. The article collects, supplements, and reinterprets well-known perspectives on happiness from the fields of philosophical anthropology, positive psychology, poetry, and folklore from around the world. The proposed personological model of happiness incorporates the results of problematizing happiness definitions, as well as insights about life-happiness, the semantics of the word "happiness," the architectonics of happiness, the paradoxes of experiencing happiness, the value dimension of happiness, “happiness impressions,” activities conducive to happiness, personality traits as subjects of happiness, the dialogical nature of experiencing happiness, variations in the life attainment of happiness, the conflicts on the path to happiness, and modern “practices of happiness.” Based on the formulation of conceptual questions about happiness and the authors’ answers to them, a reflective questionnaire, "What Is Happiness to Me?" is proposed. Working with this questionnaire can become a “practice of self-discovery in happiness” for individuals. The study presented in this article employs hermeneutic, theoretical, and reflective modeling aimed at advancing the personology of happiness, with a perspective on shaping and applying the developed models in counseling and psychotherapy practice.