Prior to arriving at the bazaar, the narrator thinks of the entire event like an epic quest. He has put Mangan's sister upon a pedestal. He conflates spirituality with romanticism in a way that makes him think he's like a knight going after some exotic holy grail for his princess (Mangan's sister). Even the name "Araby" conveyed a sense of adventure because of its associations with the East (Arab):
The syllables of the word Araby were called to me through the silence in which my soul luxuriated and cast an Eastern enchantment over me.
The narrator is completely overcome with the notion of Mangan's sister:
My eyes were often full of tears (I could not tell why) and at times a flood from my heart seemed to pour itself out into my bosom.
The narrator, an adolescent, has built up this quest to Araby in his mind. After...
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hearing the mundane and superficial conversations at the bazaar, the narrator is let down. He gets the sense that these people are not there to promote some exotic scene and experience; they are there simply to make a profit.
The narrator had built his adventure up in his mind. After seeing the reality of the bazaar as simply a superficial market, the narrator is completely let down. And this is when he realizes he's also built up this whole mythology about Mangan's sister and his role as her suitor. That's why he thinks of himself as a "creature driven and derided by vanity"; he'd not only built up Mangan's sister and the bazaar into greater things than they were, he'd done the same with himself.
Why does the narrator's overheard dialogue at the bazaar trigger the climax in "Araby"?
Having had to wait on his inebriated uncle, the boy of Joyce's "Araby" arrives too late at the bazaar and finds it to be much less than he has anticipated, as earlier when he has reflected,
[T]he syllables of the word Araby were called to me through the silence in which my soul luxuriated and cast an Eastern enchantment over me.
Instead, most of the stalls are closed and much of the large hall is in darkness. Remembering that he has come to buy a gift for Mangan's sister, the narrator moves toward a stall where he overhears a young English lady and two young Englishmen--there is "no Eastern enchantment" to them--speaking of mere trivialities. After she inquires if he wishes to buy anything, she resumes her mundane conversation with the young gentlemen.
The spell of the exotic is broken; the narrator drops two pennies against the sixpence in his pocket in a symbolic gesture of the pettiness of the scene around him. In his disillusionment, he departs in the darkness of the hall that symbolizes for him the darkness of his foolish imaginings,
I saw myself as a creature driven and derided by vanity; and my eyes burned with anguish and anger.
Unlike "Araby," the bazaar is a cheap imitation where mere trinkets are sold. But, like the Irish romantic poet James Clarence Mangan who wrote of doomed love and despair, the image of Mangan's sister in her brown dress and "silver bracelets" now conjures no "grail," but instead suggests someone tawdry who effects the narrator's despairing insight.