<p><strong>Context and relevance.</strong> In the field of practical psychology, there is an increase in interest and demand for new competencies in the area of problems associated with experiencing loss.<strong> </strong>There is a number of approaches for psychological support of crisis states in clients experiencing various forms of loss, but these approaches are separated from each other. At the same time, regret and grief, as experiences-companions of the loss of personally significant values and meanings, appear not only of an acute crisis state. Both concepts are usually identified with each other, but regret is phenomenologically associated with a subjectively controlled choice, whereas grief more often refers to an unpredictable and uncontrollable situation. <strong>Objective.</strong> We aimed to theoretically compare and substantiate the differences between the concepts of &ldquo;regret&rdquo; and &ldquo;grief&rdquo;. <strong>Methods and materials.</strong> Comparison and analysis of existing theoretical views and empirical research in the field of grief and regret. <strong>Results.</strong> Grief differs from regret by its higher intensity and acuteness of the process; subjective unpredictability of the situation; the presence of a ritual component. Moreover, grief is retrospective and concerns the lost past. Regret, on the contrary, concerns the sphere of the possible (unfulfilled) and is characterized by the experience of greater responsibility of the individual for the emergence and outcome of the situation. <strong>Conclusions. </strong>Grief and regret are irreducible phenomena and can be experienced in parallel. A significant prospect of psychotherapeutic work with grief is strengthening the client&rsquo;s contact with reality, accepting the situation of loss and building meaningful horizons in life, i.e. the vector of this work is directed from the past to the future. Work with regret is built around the restoration of subjectivity and authorship in the course of experiencing loss, reconstructing the value of the chosen alternative and finding a way to realize the value of the rejected one in current life &mdash; i.e. it focuses on the present.</p>