Within a hybrid framework of attachment and depression theory, we investigated whether introjective and anaclitic vulnerabilities can be detected in a person’s self-narrative as elicited with the Self-Confrontation Method (SCM). One hundred participants held a thorough self-investigation with one of five trainees, in which every person formulated ‘valuations’ (i.e., short sentences about personally relevant concerns) and, subsequently, rated to what degree certain feelings were evoked by every separate text. We extracted several measures from these idiographic data, including scales representing the prominence of certain themes according to the SCM typology (e.g., ‘unfulfilled longing and loss’, ‘anger and opposition’, and ‘powerlessness and isolation’). By analyzing the correlational patterns of the aggregated SCM-based measures and the questionnaire-based measures about attachment orientation and depressive personality vulnerability, we uncovered meaningful relationships. The results of a canonical correlational analysis indicated that an intensified sense of ‘powerlessness and isolation’ is a sign of a general psychopathological vulnerability (related to depression), ‘anger and opposition’ is associated with introjective features (distrust in others and need for control), and ‘unfulfilled longing and loss’ is associated with anaclitic features (pleasing and dependency). In an exploratory qualitative study, we used a cluster-based classification into attachment groups for the exhaustive screening of the content of negative valuations of (a selection of) insecurely attached persons (n = 15). This hermeneutic approach disclosed characteristic themes for each of the preoccupied, dismissive-avoidant and fearful-avoidant attachment styles which are discussed in great detail.