This article suggests that unlike their well-off counterparts who apply to college in the fall and know they will go somewhere when the applications have been sent, low-income students face unique challenges that extend the process in a manner entirely different from the wealthy. The notion that college-going is a cultural interpretation is circumscribed by constantly shifting forces rather than a rational choice. The author offers portraits of three 17-year-old male Latino youth who attend the same school to demonstrate how different their stances are toward college. The purpose is to move away from the essentialized notions of student identity. Even with three seemingly similar students the manner in which they interpret how to go about applying for college differs. The narrative strategy works from a standpoint that has sought to understand the meanings of applying to college from the perspectives of the three youth with whom the author has worked.