Background Like many other countries, Singapore needs to support its ageing population by attracting more doctors into general practice (GP) and family medicine (FM). To achieve this requires a better understanding of what attracts or deters medical students. We conducted a cross-sectional survey among medical students in Singapore. Methods An online survey was distributed to students from all three medical schools to understand their likelihood of choosing primary care careers, what they valued in their careers, their attitude towards different aspects of general practice and family medicine relative to other medical fields, and the positive and negative perceptions of primary care held by themselves, their lecturers, and clinical mentors. They were able to elaborate the negativity encountered in the open-ended questions. Quantitative data was analyzed with descriptive statistics, principal component analysis, and linear regression; qualitative data was analyzed thematically. Results The survey was completed by 391 students. Slightly over half indicated a likelihood of choosing a career in primary care. For their own careers, the students valued job satisfaction and career development opportunities the most. They perceived careers in primary care as being most likely to offer reasonable hours and close patient relationships, but least likely to offer career advancement potential relative to other medical fields. Their likelihood of choosing primary care careers was significantly predicted by what they value in their own career and their attitudes toward GP/FM relative to other medical fields, but not by the perceptions of GP/FM by others. Free-text responses illustrated how students encounter derogatory comments about GP/FM: the work being “mundane and repetitive”, the careers non-competitive, and the doctors poor in clinical competence. Conclusion While the shortage of primary care doctors is a global issue, our findings highlight the value of situating inquiries in localized contexts. Medical curriculum should emphasize the critical role of primary care in the healthcare system and primary care doctors should be given due recognition to build a strong and motivated primary care workforce to serve the future healthcare needs of the population.