There is a critical need to better understand the factors that contribute to men’s underrepresentation in female-stereotypic, communal careers, such as those in the HEED (Health Care, Elementary Education, and the Domestic sphere) domains. Although vocational interests have been widely cited as a key contributing factor to the HEED gender gap, little research has empirically examined the relationship of vocational interests to HEED career choices. Drawing on Holland’s (1997) RIASEC (Realistic, Investigative, Artistic, Social, Enterprising, and Conventional) theory and its corresponding concept of person-environment (P-E) fit, we examined how vocational interests and interest fit (i.e., compatibility between a person’s interests and HEED occupations) predict HEED career choices and aspirations. We analyzed responses from 41,651 employed and unemployed persons who completed an online career interest survey. Results, based on multiple logistic regressions, indicated that Social interest (i.e., interest in traditionally feminine work activities) and interest fit were positively associated with HEED career choices and aspirations. Investigative interest was positively related to HEED career choices, but not aspirations. All other RIASEC dimensions—Realistic, Artistic, Enterprising and Conventional—were negatively associated with these outcomes. Moderation analyses further revealed that the positive effects of interest fit on HEED career choices and aspirations were similar for men and women. Practical implications for career counseling, person-job matching, and improving gender diversity in HEED are discussed.