This chapter investigates the relationship between ambivalence and Oedipal guilt. The latter is one of Freud’s versions of the father complex, each of which serve to prohibit jouissance and regulate desire. In the Oedipus complex, the law is present from the outset, and when it is transgressed, the subject experiences jouissance and guilt. The neurotic subject experiences guilt even for unconsciously desiring something prohibited by the Oedipal law. The neurotic hides these guilty secrets from himself and suffers from symptoms constituted on the basis of his repression. As the hallmark of obsessional neurosis is ambivalence, this chapter explores notable obsessionals, including Freud’s Rat Man, Breaking Bad’s Walter White, and James Thurber’s Walter Mitty. Far from Oedipal ambivalence being an outdated experience, this chapter shows how it, and the guilt associated with it, still functions in today’s time. For example, in contemporary pleasure-seeking society, Oedipal guilt may hide in anhedonia, or the state of being without pleasure. The authors pay particular attention to users of the Manosphere, which is a network of websites promoting men’s rights movements and guides for attracting women. Groups who participate in the Manosphere such as the incel community (involuntary celibates) are united by their common deficit of jouissance, their common lack of sexual partnerships, and also by their jealouissance, or their satisfaction in being jealous. Their hatred is aimed at men who are more successful with women and who resemble the primal or Oedipal father, just as their hatred is aimed at women, as the desired but out-of-reach object.