The following essay is a dialogue between two high school English teachers at a small, progressive public school on the Lower East Side of Manhattan. Throughout their dialogue, Jen, whose voice appears in italics, and Kim, whose voice appears in plain text, discuss the factors that motivated their decisions to become teachers, tell of the distinct impact that Obama's election has had on their practice and their students, and suggest that many students feel ambivalent about the extent to which President Obama could effect real change in their lives. The article concludes with an anecdote, suggesting that educators can engage in a process of inquiry with students to help them make connections between Obama's election and their lives. (Contains 2 notes.)