With the dramatic increase in competitiveness in college admissions evident by falling acceptance rates over time, the college planning process has become of great importance to high school students and their parents. As a result, high schools are redesigning their college counseling programs to better serve their students in this increasingly competitive environment. However, college counseling programs are just one piece of the puzzle. The parent-child relationship during the college planning process also plays an important role in achieving a successful outcome. This study presents results from a survey in which high school students answered questions in the form of messages to their parents during the college planning process. We surveyed 138 high school juniors from two private schools that differ in contextual factors (e.g., a private boarding school versus a private non-boarding parochial school). We applied the Grounded Theory coding method to code open-ended survey responses into common themes that were used to test three hypotheses regarding school-specific contextual factors and the frequency of common themes in student messages to their parents. One key result from our analysis is that students at private boarding schools are likely to express greater fear of parental control and disappointment than students at private non-boarding parochial schools. We also found that students at schools with less extensive college planning programs express greater need for parental help in the college planning process. These findings provide evidence that contextual factors are important in the college planning process and could be useful to the design of college planning programs at high schools.