As a child, Stephen Dedalus's only contact with women was on school holidays and such. This doesn't change as he grows older; Stephen is constantly enrolled in boys only schools with exclusively male teachers. Because of this isolation from the so called fairer sex, Stephen has an odd relationship with girls. It's not unusual for young boys to be awkward around girls, but Stephen takes the normal awkwardness to a new level. He freezes around girls, never making the first move. Part of this is due to the character Mercedes from The Counte of Monte Cristo who Stephen compares all females to. He is constantly waiting for a mysterious female figure to "encounter" him as Joyce phrases it. To me, encountering means making the first move. Because of this expectation, Stephen doesn't make a move on Emma or any other girls. This is also why his first sexual experience with a prostitute is so significant. He "wandered" into the red district and waited for one of the prostitutes to come to him.
In class, we discussed what Stephen wanted from the prostitute. The way Joyce words it is "embrace" etc. implying that he wants a maternal relationship, but just before this Stephen goes on about his sin and lust . I don't think anyone could change their mind that easily; it's a bit of a stretch to go from lust and longing to wanting a motherly figure. Then there is apparently a holy part of his interaction with the prostitute(s). Stephen is a little obsessed with the Virgin Mary (Mother Mary, etc.) and the way Joyce writes this section implies at least a marginal amount of religiousness by writing about "heads looking heavenward" and such. Then, there is Stephen's ritual after this encounter. Every night Stephen "wanders" to the red district, almost religiously he sticks to this trend. Once in the brothel area he waits again to be encountered, waiting once more for his Mercedes to make an appearance.
I don't see any reason the prostitute couldn't represent all of these things. The woman fulfills all of the needs Stephen needs a woman to fill. The entire experience starts with Stephen being "encountered" fulfilling his fantasy about Mercedes--having a woman make the first move. He has been kept away from his mother during school with no figure to step in and fill that maternal role, so he wants to be held by the woman just like his mother held him to her breast; he just wants to feel safe like he did with his mother. But, this safety is not unaccompanied by other feelings. Stephen is still lustful, and he is able to satisfy this lust with the woman, as well as his fantasy Mercedes. I think the safety and lust and Mercedes are all intertwined. To Stephen, it's not his fault he is lusting after a woman, she encountered him. Stephen perceives a certain amount of safety in this. It is as bad, as unholy, if it's not his fault. And it isn't as sinful if he's the best at sinning, because he is pursuing what he is best at in his mind.
You're right that Stephen's tendency to view girls and women more as "images" than as three-dimensional human beings can be traced back to his obsession with the figure of Mercedes from _The Count of Monte Cristo_. But we can also trace his own passivity and detachment (which you describe here as a kind of paralyzed awkwardness) to his idea of the romantic hero of the novel. Remember his "sad, proud gesture of refusal," "Madame, I never eat muscatel grapes." Stephen imaginatively recasts his more or less normal shyness and awkwardness into a kind of virtue. We see him kind of playing this role with Emma on the tram: cool and detached, depending on her to make the first move. This is probably Stephen's natural tendency, and his awkwardness very likely has to do with how little actual experience he has around female human beings, as you note. But he manages to view it in a new way--as a kind of romantic quality, his "silent, watchful manner"--because of the literary model. The solitude is less awkward if you imagine yourself as the tormented romantic hero of a novel.
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