Challenges to engage pharmacy customers in medicine dialogues at the counter have been identified comprising a new and extended clinical role for pharmacists in the health care system. This article seeks to expand understanding of factors involved in successful interaction at the pharmacy counter between customers and pharmacy staff to develop their relationship further. Practical challenges to customer encounters experienced by community pharmacists are discussed using theory from the field of mainly inter-relational communication and particular studies on pharmacy communication. Preconceived expectation of customers, the type of question asked by pharmacy staff, and differences in perception of illness and medicines between staff and customers are discussed. Both staff and customer influence the outcome of attempts by pharmacy staff to engage customers in dialogue about their medicine use through a complex mechanism of interaction. It is recommended that practitioners and researchers begin to distinguish, both theoretically and practically, between the content of a conversation and the underlying relationship when exploring and further developing the therapeutic relationship between pharmacy personnel and customers.