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Given the disproportionate representation of women in science and mathematics fields, boldness, a socialized orientation towards mathematics, may relate to the pursuit of advanced mathematics. This study uses survey data and quantitative methods to examine (a) sex differences in boldness in the postsecondary population, (b) how bold problem-solving tendencies vary between postsecondary mathematics courses, and (c) how boldness relates to the mathematics load of students’ majors. Sex differences favoring males do exist. Students in advanced classes have higher bold problem-solving tendencies than those in lower-level classes. Boldness does not predict the mathematics load of a student’s major after including affective variables. Thus, while boldness relates to doing advanced mathematics, majoring in mathematics-intensive fields also requires valuing mathematics.