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Frequent use of anonymous helplines is often framed as problematic from a service perspective. This study aims to explore how frequent users themselves perceive the helpfulness of repeated helpline contact and to examine tensions between user and staff understandings of effective helpline communication. The study draws on qualitative interviews with 31 frequent users across ten Danish helplines, covering telephone-, chat-, and SMS-based services. The analysis is conducted in dialogue with prior findings on helpline staff's communicative ideals, using a framework distinguishing between transformative, relational, and respectful communication. Frequent users experience helpline interactions as micro-transformative, providing immediate emotional regulation, relief from intrusive thoughts, and temporary containment of loneliness. Relational presence is experienced as meaningful change in the here-and-now. Frequent helpline use is best understood as a situated, relational community practice rather than an individual deficit, with important implications for community-based mental health support.