Purpose The aim of this study was to determine descriptive characteristics of dental students, to investigate their professional expectations, career decision criteria, and related factors; to examine how (if any) seniority in school affects these. Subjects and Methods During the period of 2018-2019, all 1-5 grade students (n = 754) of Hacettepe University Dental School were invited to participate and those who accepted had filled under observation a standard questionnaire form of 35 questions (83.4%). In the analysis of the data, descriptive statistics, chi-square, Student's t-test and ANOVA and Odds ratio methods were used. Results In this cross-sectional study, 66% of the group were female, age range was 18-30 (mean±SD= 21.2 ± 1.7). The most common reasons for choosing dentistry were “financial benefits”, “job security” and “professional status”. “Undertake specialist training” (80.2%) was the most common short-term expectation after graduation; two most common long-term expectations were “having a private clinic” (57.9%) and “completing specialization training” (56.0%). The most important factors affecting the post-graduation working plans were work-life balance and economic stability. Conclusion It is recommended to provide adequate counseling and guidance to students about potential career paths to maximize a balanced and widely accessible oral health service delivery across the country with more motivated dentists. Qualitative research may improve our understanding of how dental education can be improved to fulfill students’ expectations from school, and to motivate dental students towards general practitioning in the future.