Pharmacists must provide pharmaceutical advice to customers to enable them to self-medicate safely. However, if pharmacists experience any difficulties in selling over-the-counter（ OTC） drugs, they may not be able to demonstrate their expertise adequately. This could prevent customers from using OTC drugs appropriately. In this study, 200 community pharmacists were requested to narrate any difficulties they had previously experienced while selling OTC drugs. Descriptions by 94 pharmacists who appealed to their difficulties when talking with customers were analyzed qualitatively. We revealed the following five perspectives：“invading the privacy of customers,” “expertise required despite a lack of information,” “environment surrounding the pharmacy,” “rules for OTC drug sales,” and “improving public understanding of the roles of pharmacists.” These perspectives arose from the pharmacists’ attempts to fulfill their responsibilities. In the future, it will be necessary to mitigate the pharmacists’ difficulties so that pharmacists can utilize their expertise to deepen their relationships with customers.

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