In his "Pursuits of Happiness: The Hollywood Comedy of Remarriage" (1981) as well as in "Contesting Tears" (1997), Stanley Cavell has convincingly argued that the question of marriage—“is it better to be alone than in pair?”—has the philosophical legitimacy of classic questions such as “What can I know?” and “Why is there something instead of nothing?” In this regard, the structure of the “comedy of remarriage” is significant. It does not consist in illustrating how two people get together, but rather in narrating how they get back together. This genre of comedy focuses on the overcoming of a separation—an inner obstacle—rather than on the overcoming of external obstacles. Drawing on Cavell’s well-known work, this contribution aims at investigating the political dimension underlying romance. The chapter illustrates and analyzes the comedy of remarriage as a paradigm through which we can understand the political dimension of marriage and the romantic dimension of everyday politics.