What is confusing about the encounter with O'Brien?

Answer 1

The encounter with O'Brien is confusing because it blurs the lines between loyalty and betrayal. Winston initially believes O'Brien to be a fellow dissenter against the Party, only to later realize that O'Brien is actually a loyal Party member who has been manipulating him. This deception highlights the pervasive atmosphere of mistrust and doublespeak in the Party, leaving Winston—and the reader—uncertain about who to trust. The encounter underscores the complexities of resistance and the psychological torment inflicted by totalitarian regimes.