Family physicians commonly find themselves in difficult clinical encounters. These encounters often leave the physician feeling frustrated. The patient may also be dissatisfied with these encounters because of unmet needs, unfulfilled expectations, and unresolved medical issues. Difficult encounters may be attributable to factors associated with the physician, patient, situation, or a combination. Common physician factors include negative bias toward specific health conditions, poor communication skills, and situational stressors. Patient factors may include personality disorders, multiple and poorly defined symptoms, nonadherence to medical advice, and self-destructive behaviors. Situational factors include time pressures during visits, patient and staff conflicts, or complex social issues. To better manage difficult clinical encounters, the physician needs to identify all contributing factors, starting with his or her personal frame of reference for the situation. During the encounter, the physician should use empathetic listening skills and a nonjudgmental, caring attitude; evaluate the challenging patient for underlying psychological and medical disorders and previous or current physical or mental abuse; set boundaries; and use patient-centered communication to reach a mutually agreed upon plan. The timing and duration of visits, as well as expected conduct, may need to be specifically negotiated. Understanding and managing the factors contributing to a difficult encounter will lead to a more effective and satisfactory experience for the physician and the patient.