Joyce adds complexity to the Homeric parallel by comparing Stephen to Scylla, an "enemy" of Odysseus-Ulysses (Bloom). In a sense, Stephen, with his carping logic, is an opponent of the more mundane and practical Bloom, and, in the later stages of Ulysses, Joyce portrays the impossibility of the two men's reaching any satisfying or permanent relationship. Also, by placing Stephen in a generally Homeric context, Joyce suggests that Stephen must go through his own odyssey in the novel — that is, he must attempt to reconcile the flesh with the spirit, the mind with the body, and his "deep" and grandiose thoughts with workaday concerns. Finally, it may well be plausible to see the six-headed hydra, Scylla, in the six principals with whom Stephen debates: Lyster, Best, Russell, Eglinton, Mulligan, and Stephen himself in his role as a self-doubting skeptic who does not believe his own theory of Shakespeare or any other "theories," including religious teachings, that he has come across thus far in his life.
The episode opens with Stephen disputing aesthetics, the new Irish writers, and other matters with the Quaker librarian Thomas William Lyster, Director of the National Library; with John Eglinton, an influential Anglo-Irish essayist and editor of the short-lived journal Dana; and with Russell. They are soon joined by Richard I. Best, Assistant Director of the National Library. Russell's leavetaking ends the initial section of "Scylla and Charybdis."
Stephen begins to deliver his Shakespeare thesis, but other thoughts intrude upon his consciousness. He notices, for example, that John Eglinton trumps Stephen's theories with an "elder's gall"; and, to counter Eglinton, Stephen forces himself to smile in the manner of his former confidant Cranly, who figured prominently in Book Five of A Portrait. He then remembers the telegram that he sent to Mulligan at The Ship pub, canceling their luncheon appointment. A mention of Haines causes Stephen to feel guilty: He has smoked Haines's tobacco and, in general, he has treated the Englishman badly. Stephen also remembers the money that Russell lent him for food (which Stephen spent on a prostitute, Georgina Johnson), and he is reminded of Deasy's injunction in "Nestor" that a man's proudest boast should be that, despite all, he "paid his way"; thus, when Stephen muses upon his indebtedness to Russell, it gives rise to the notorious pun "A.E.I.O.U.," after he has thought of another "father figure," Father Conmee, S.J., who saved Stephen from a whipping when he was a boy at Clongowes Wood College (actually an elementary school) in Book One of A Portrait. In this general context of guilt, Stephen is also reminded of his mother's death, and we learn that despite his somewhat priggish refusal to pray at her bedside, he did indeed weep for her: "I wept alone." As Stephen speaks of Anne Hathaway's seduction of young William Shakespeare, a woman several years Shakespeare's senior, Stephen cannot help but muse about his own future and wonder when some buxom wench, some "greyeyed goddess," will "overtip" him in a cornfield: "And my turn? When?"
