Kersti Merilaas (1913–1986) and August Sang (1914–1969) have, both in their early poems and later years, written poignantly about loss in the broadest sense of the word: losing loved ones to death, dreams to reality, freedom to totalitarianism. Yet their poetry remains, if not entirely optimistic, always attentive to ways in which life, love and creative work inevitably continue in a world where the experience of loss is also inevitable. On the one hand, their poetry shows clear understanding of the limits of human reality. On the other hand, while they realize that certain lines cannot be crossed, neither in life nor art, they refuse to accept ready-made concepts of how these lines – impossibilities, disappointments, failures, personal and collective traumas – define and articulate the reality and our understanding thereof. Scepticism towards simple, black and white oppositions and evaluations is thus an important theme in their poetry, but it is also a basis for a more general reflection inspired by their life and work. With Sang and Merilaas, it is quite impossible to separate personal relations and family life from partnership in creative endeavours, personal history from that of the entire Estonian literature, original writing from translating, individual thought from a constant dialogue with other people brought close by life and/or literature. The discussion of these issues in this article is based on some of their poems (most of them from Kersti Merilaas’ last collection Antud ja võetud („Given and taken”), 1981) and critical texts about their work.