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Abstract Letters of Recommendation (LORs) are widely utilized for admission to both undergraduate and graduate programs, and are becoming even more important with the decreasing role that standardized tests play in the admissions process. However, LORs are highly subjective and thus can inject recommender bias into the process, leading to an inequitable evaluation of the candidates’ competitiveness and competence. Our study utilizes natural language processing methods and manually determined ratings to investigate gender and cultural differences and biases in LORs written for STEM Master’s program applicants. We generate features to measure important characteristics of the LORs and then compare these characteristics across groups based on recommender gender, applicant gender, and applicant country of origin. One set of features, which measure the underlying sentiment, tone, and emotions associated with each LOR, is automatically generated using IBM Watson’s Natural Language Understanding (NLU) service. The second set of features is measured manually by our research team and quantifies the relevance, specificity, and positivity of each LOR. We identify and discuss features that exhibit statistically significant differences across gender and culture study groups. Our analysis is based on approximately 4000 applications for the MS in Data Science and MS in Computer Science programs at Fordham University. To our knowledge, no similar study has been performed on these graduate programs.