This research is the study and comparison of two philosopher couples: Jean-Paul Sartre and Simone de Beauvoir, and John Stuart Mill and Harriet Taylor. Both partnerships exhibit characteristics of an unconventional relationship. Sartre and de Beauvoir had an open relationship, in which both partners were free to commit unlimited adultery. Mill and Taylor were emotionally committed to each other, while Taylor was legally bound to another man. This research examines the individual decisions and consequences of challenging the institution of marriage set by societal norms. With the current growth of unconventional relationships, whether open, homosexual, or interracial, it is especially important for us to examine these kinds of relationships and how they are viewed in the traditional mold of society.