Sophomoric Philosophy is an account of Alejandro ("Alex") Lopez, a 30-something first generation Mexican-American accountant. He works for a large corporation and is torn between his desire to lead an artistic life and the reality of his mundane existence in contemporary Chicago. Alex contemplates events and patterns both in his adult life, and his teenage years growing up in a blue-collar suburb. While doing so, Alex recounts cheating on his ex-girlfriend with her best friend, his anxiety when making dating decisions, his struggle to identify with Mexican culture, and causing trouble, partying and having sex as a teenager. Alex evaluates his attempts to make a life out of his artistic interests, which he always abandons for a more financially secure lifestyle. Despite this compromise, Alex still can't let go of his interests and the childhood philosophy he and his friends discussed in the streets and backyard parties of suburban Chicago.