We present a quantitative, data-driven machine learning approach to mitigate the problem of unpredictability of Computer Science Graduate School Admissions. In this paper, we discuss the possibility of a system which may help prospective applicants evaluate their Statement of Purpose (SOP) based on our system output. We, then, identify feature sets which can be used to train a predictive model. We train a model over fifty manually verified SOPs for which it uses an SVM classifier and achieves the highest accuracy of 92% with 10-fold cross validation. We also perform experiments to establish that Word Embedding based features and Document Similarity based features outperform other identified feature combinations. We plan to deploy our application as a web service and release it as a FOSS service