This chapter examines how the intersection of students' race-ethnicity and gender is associated with their motivational orientation toward college. Students' motivational orientations were evident in their reasons for going to college and in their adjustment struggles during the first year. This chapter focuses on how Latinx men's motivational orientations can either align them with or place them at odds with their institutions' dominant cultural orientation. In comparison to Black men, Latinx men were more likely to come from very low-educated and immigrant families. This means that their home life did not include access to a knowledgeable adult who could guide them through the college process, from its very beginning in dealing with applications, school choice, and financial aid, to advice for managing the stress of finals week or support in persistence decisions.