The investigation explored 12 adults’ past experiences of physical awkwardness. Hermeneutic phenomenology, a descriptive and interpretative methodology, uncovered feelings and meanings associated with childhood reminiscences of physical awkwardness, from 18 semi-structured interviews. Findings focus upon four themes, namely: “failing and falling,” “hurt and humiliation,” “worrying and wondering,” and seeking ways of “avoiding awkwardness” in the future. A heightened awareness of the subjective lived experience of those who are awkward in physical activity and sport situations would alert teachers, coaches, and others of the potential emotional and social consequences associated with it and the need to address the problem of physical awkwardness, in particular, during early growth, maturation, skill development, and learning.