ABSTRACT Purpose: Although the relation between health and well-being is deemed conceptually important, it is diverse and intractable. The aim of this small-scale study is to reveal different possible relations of the concepts of health and well-being, interrelation of these relations and consequences of implied normative expectations in the relations. Method: Primary data originate from course literature in Swedish health education. Additional data included scientific articles and website content (collected from WHO and via Google) and were analysed with objective hermeneutics. Results: Congruent, complementary and coincident relations were found. In congruence, health and well-being are synonyms. Complement relations contain: “quality” with well-being as overall aim, “plurality” with health as umbrella term, “well-being as positive health”, “enhancement” with health and well-being potentially boosting each other and “subjectivity/objectivity” with objective health complemented by subjective well-being. In coincidence, health and well-being are counter-intuitively regarded unlinked, which may challenge expectations concerning health promotive activities. Independent and affiliated relations were identified. Conclusion: In congruence and complement, health and well-being are mostly aligned whereas in coincidence, their quality may be decoupled. In the discursive climate of second modernity, the relation of health and well-being tends to conflict and ambiguous coincidence, demanding ambiguity tolerance as key skill.