We examined how high school and college students make an important real-life decision: choosing the courses they will take in the upcoming academic year. Current high school and college students completed an online survey. Participants listed their course choices and the criteria they used to make their decisions (e.g., time a course meets, subject matter of a course) and also responded to a modified version of the Reactions to Decision instrument (Galotti, Tandler, & Weiner, 2014), which measured their affective reactions to the decision-making process. College students tended to list more options and criteria when describing their decisions than did high school students. High school students rated the future importance of their decisions higher and their independence in the decision-making process lower than did college students. College students reported using information specific to courses, such as instructor, time a class is scheduled, and the requirements a course met, as criteria when using courses more than did high school students. High school and college students who listed more criteria tended to be less certain and comfortable with the decision-making process than their peers. We discuss the context of this decision for each group of students.