This article explores the questions of marriage and divorce as discussed by Stanley Cavell in his study of Classical Hollywood comedies, in which he considered a popular subgenre of the American comedy of the thirties and forties that he dubbed the “comedy of remarriage”. It focuses on Cavell’s analysis of a series of films and the way these comedies belong to a specific American school of thought with case study of THE AWFUL TRUTH(Leo McCarey, US 1937). It then seeks to identify traces of Kierkegaard’s moral legacy, by way of Wittgenstein’s influence on the American thinker, in Cavell’s original approach to marriage and divorce in light of his discussion of philosophical skepticism.