In this section of 1984 George Orwell is juxtaposing two relationships: the relationship of Winston and Julia with the relationship of Winston and the prisoner.
In a sense, everyone in Oceania is a prisoner. They are all terrified of the Thought Police and under constant surveillance. One of the goals of the Party and Big Brother is to prevent people from forming meaningful relationships with one another—they want the only relationship people to value is their relationship with the Party.
Winston and Julia are taking a great risk by engaging in their secret (or so they think) affair. They succeed in conducting the clandestine affair for a while, but they have to be so careful that they are really still imprisoned in a way—they must hide and sneak around.
At the point when they see the prisoner they are in the open and afraid to even look each other in the eyes—it might give them away. They can, however, look at the prisoner without fear.
At this point the juxtaposition becomes ironic (irony is something surprising or unexpected). The final lines of the chapter are:
. . . they stared steadily in front of them, and instead of the eyes of the girl, the eyes of the aged prisoner gazed mournfully at Winston out of nests of hair.
Because of Orwell’s juxtaposition, the reader is mentally making a comparison of Winston/Julia with the prisoner/Winston. Here’s the irony involved—Winston and Julia cannot look each other in the eye, but the prisoner is able to look Winston in the eye. The word “mournfully” implies a certain degree of emotional honesty: the prisoner is the only character in this scene who is able to react without fear of detection; he doesn’t have to hide his emotions like Winston and Julia. In a way, the prisoner has more freedom than they do.
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