In this paper I discuss the melancholy nature of happiness in two short stories by Herman Melville, The Piazza and Bartleby, the Scrivener. Applying Melvilles passage from Moby-Dick on the conceit of attainable felicity as well as Thomas Hobbess statement on the progress of the desire from Leviathan, this essay traces the pursuit of happiness of the main characters in these two stories. While analyzing the tales separately, I also argue that they follow a similar pattern: the friendly narrator of each story sets out to achieve a greater level of happiness, but finds his pursuit altered and complicated when he meets an incurably unhappy person. As the narrators try to account for the sad characters they meet, they find that happiness always involves compromise.