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Background/Objectives: Higher education institutions must improve the attractiveness and retention of the nursing profession to address the widespread shortage. This pilot multimethod study aimed to preliminarily understand the relationship between motivations for enrolment and dropout among first-year undergraduate nursing students. Methods: A two-step approach was conducted among first-year nursing students from five Italian universities involving: (a) a baseline quantitative online survey collecting their characteristics and motivations for enrolment; (b) a follow-up semi-structured interview qualitative data collection among students who dropped out. Descriptive and inferential statistics were used to describe the motivations for enrolment and differences between universities. Dropout motivations emerged from inductive content analysis, with data categorisation according to Urwin’s framework. Results: A total of 759 students completed the online survey. Primary motivations for enrolment included the desire to be useful (88.8%), help suffering people (84.3%), and find employment (74.2%); 22.3% cited unsuccessful admission to another university as motivation for enrolment. Of the 141 students who discontinued, 31 were interviewed (22%). Eleven categories and three themes were identified. More than half of the participants dropped out due to interest in other courses and lack of aptitude, while a smaller number cited personal circumstances. Other motivations for dropout were related to negative learning environments or feelings and difficulties related to course characteristics. Conclusions: This study provides an initial insight into these complex phenomena that will be instrumental in understanding data from an Italian multicenter cohort study. The findings can inform recommendations and strategies to strengthen the future nursing workforce.