The concept of linguistic indirectness is well established within the field of pragmatics, in which it has been observed that speakers express ideas directly and indirectly. We integrated the analysis of linguistic directness and indirectness with the examination of two established measures of parental emotion socialization through reminiscing: elaboration and emotion explanations. We examined the unique associations of parents’ direct and indirect elaboration and emotion explanations with preschoolers’ emotion regulation and psychosocial adjustment. Participants were 55 parent–preschooler dyads (31 girls, 24 boys). The dyads reminisced about positive and negative events. Conversations were coded for parental elaboration, parental use of emotion explanations, and parental linguistic directness and indirectness. Children’s emotion regulation was observed during standard tasks, and teachers reported on children’s psychosocial adjustment. Multivariate regressions including direct elaboration and direct emotion explanations indicated that parents who engaged in more indirect elaboration when discussing positive events had children with worse emotion regulation. Parents who used indirect emotion explanations when discussing positive events had children with better psychosocial adjustment. Parents’ indirect speech during negative event discussions was not related to child outcomes. The results suggest differential functions for indirect elaboration and indirect emotion explanations in relation to children’s social outcomes, and support the utility of examining linguistic indirectness.