This paper describes the use of personal computer simulations for teaching adaptive interviewing skills. The training applications described here require embedding affective responses by synthetic characters into the interviewing process to encourage adaptive learning. The concept is that the student has to modify his or her approach to completing the interview by taking into account the affective responses of the characters. Simulations that provide variations on basic scenarios designed to meet specific learning objectives allow the student to participate in deliberate practice of subtle interaction skills in the context of requirements to achieve specific interview results. The paper describes three applications of our synthetic character technology: training field interviewers prior to conducting house-to-house surveys, training medical students on trust-building skills with pediatric patients, and training police officers to de-escalate encounters with the mentally ill.