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Martha Nussbaum and Sigmund Freud have in common in recognizing the importance of emotions, sexual energy or libido, and love in the formation of society, community, and nation. They also discern the significance of women in embodying the social community or liberal democracy for the future, founded on fraternity, equality, and liberty. I try to figure out how Nussbaum’s and Freud’s explorations of social energy, emotional and sexual, and their insights into the significance of women in drawing the political potentiality for the future, can be explicated with the story of Twelfth Night. Thus, first, I investigate several forms of love relationships that associate subjects with others: Orsino, Viola, and Olivia in the main plot; Sir Toby, Sir Andrew, and Maria in the subplot adjoined in their mocking of Malvolio; Antonio and Sebastian; and lastly, Feste. Then I argue that Malvolio’s fantasizing over marrying Olivia and thus becoming a Count, and Orsino’s wooing of Olivia, both are similarly conditioned by narcissism, self-aggrandizement, and envy as seen in masculine heterosexual loves in this play. These masculine heterosexual loves are distinguished from feminine heterosexual love as seen in Viola’s love for Orsino and homosexual love which is either lesbian, Olivia’s love for Viola, or gay, Antonio’s selfless love for Sebastian, on the other hand. Especially, I pay attention to the lesbian or female friendship that unfolded between Viola and Olivia, and between Olivia and Maria, which creates fraternity, equality, and liberty in the human relationships among female characters.