Medical students training incorporates learning how to take a medical history with an increasing focus on professional bedside manner and communication training. Upon successfully training with simulated patient contact students are eligible to rotate on clinical wards. In this study we evaluated whether students feel sufficiently prepared for taking medical history with real patients and a possible correlation between self-assessment and year of study, number of weeks spent at a clinical rotation, gender or age. A self-administered questionnaire with 21 questions about five main categories: social skills and communication, demeanour, expertise, ability to combine communicative and expert skills/knowledge was send to third, fourth, fifth and sixth year students at the Medical University of Vienna. The majority evaluated their own skills as sufficient, improving with increasing year of study and number of weeks spent at an internship. The best-rated main category was social skills and communication, the worst expertise, especially taking a medical history in special settings. However, in contrast to social skills and communication, expertise saw an improvement with increasing time of study and weeks of practical training. Gender-specific differences could be shown regarding taking medical history in empathy and politeness (female>men) and in appearing less insecure and embodying the role of physicians (men>women). A weak negative correlation was demonstrated between age, and ability to combine communication skills with expertise. This data indicates the need for re-evaluation of the training of social and communicative skills at medical universities. A focus should be placed on examining reasons for a subjective lack of improvement in social skills and communication in the transfer of expert skills. Further studies should be conducted to evaluate the relevance of gender-specific differences and the possible necessity to integrate them into developing curricula.