- Why is the skull faced man and not the chinless man taken to room 101?
This one is a curious case. From reading the scene take place it would seem that the chinless man should be taken to room 101 based on his actions. He takes some bread from his pocket and attempts to give some to the skull faced man. When Winston tries to reach into his pockets earlier in the chapter, he is yelled at by the telescreen. The chinless man is also yelled at by the telescreen after his attempt at a good deed, and yet he still is not going to room 101.
Without knowing a lot, we are inferring here that room 101 is a form of punishment, based on the skull faced man's response to being sent there. He will do anything to not go there. The decision to send him there could be based on more than the actions at the present moment of the chapter. Even though the chinless man is on the Party's bad side for attempting to give some bread away, the skull faced man's "crime" could be way worse but we don't know his background or history. This also could just be a cruel way the Party punishes people, with no reason at all. You could be minding your own business, like the skull faced man, and still get sent to room 101.
- How have Winston’s feelings for Julia changed?
Winston definitely loved Julia back when they were regularly meeting before their arrest. He was happy and his mood and body were shifting to show that I think. Especially his body, his ulcer stopped bothering him and he started to gain some weight. After their arrest I think Winston's feelings for Julia have changed just out of priorities. How can you think of love in a place like this??? It smells, you are surrounded by telescreens, the guards can beat you at their will, and there is this room 101 place that people are frightened of.
Winston is kind of fighting for survival at this point. The last thing on his mind would be Julia, but then again, if they truly loved each other, wouldn't they still think about each other and wonder if the other is safe? He actually states that he loves her in this section, but then quickly reverts back saying he actually feels no love and never wonders what is happening to her. Winston even asks himself if he could take double the pain if it meant saving Julia, and he decides that he can't do it. Winston is truly solely focused on himself in the prison, and I don't necessarily blame him. Maybe deep down he knows that there is nothing that could be done to save either of them, so there is no use playing the fantasies in his head. The person he loved will never be seen again, and he might as well get that through his head now. Winston mentions how in this place you could not feel anything, and love for Julia would definitely be a part of that "anything" category.
- What do you make of seeing O’Brien arriving?
O'Brien enters the room where Winston is imprisoned not as an inmate, but as somebody of the Party. Winston is shocked to see him, but according to O'Brien he really shouldn't be. O'Brien states to Winston how he knew that this is where his path would lead all along. The place where there is no darkness, and lo and behold, it is a prison. O'Brien is here not as a comrade, but as his interrogator and handler. I think it is clear that O'Brien has deceived Winston, and got him to play along with the brotherhood/Goldstein narrative to incriminate himself for an easy arrest by the thought police. Now I start to wonder if this con goes all the way back to the beginning of chapter 1, where O'Brien gives Winston a look. From there, Winston goes into believing that this subtle communication was one of trust and acknowledgement of a common inner struggle to want to break free from the Party. Looking at it now...was it all just a set up?
We are not clear yet on O'Brien's role in Winston's arrest or what is about to take place in the Ministry of Love. His cryptic words telling Winston that he always knew it make me think that Winston has been down the path before possibly. Maybe he has been stuck in a groundhog day scenario, reliving his life trying to get to the brotherhood and starting a revolution against Big Brother. Each time, O'Brien is there to thwart that plan...