In the first chapter of Book Two, Winston was walking towards he men's room and he noticed a dark-haired girl with her arm in a sling. She fell and Winston rushed to help her. When she walked away, he realized that she had passed him a note which had said "I love you." Winston seemed confused since he did not know whether to believe her or not. He had seen her around and had always suspected her of being a political spy who was monitoring his behavior. But before he could think about this any further, Parsons interrupted him with talk about his preparations for Hate Week.
Winston was hesitant to talk to her for a couple days but he finally gathered the courage to sit at the same lunch table with her. Once they started talking, the dark-haired girl had suggested meeting in Victory Square where they would be able to hide from the telescreens amidst the movement of the crowds. Once they were in Victory Square, she told Winston that there was a place that they could meet so that they can have their tryst. At the end of the chapter, they managed to hold hands briefly
In the second chapter of Book Two, Winston and the girl execute the plan and they meet up in the country. Winston still felt a little lost but he no longer believes that the girl is a spy. The girl tells him that her name is Julia, and soon they move into the woods where they go make love. Winston feels that this experience is nearly identical to the passionate sexual encounter that Winston had dreamed of . He tells Julia he loves her more because it meant that more Party members are committing crimes
I feel that Winston's rebellious streak has taken a bit of a darker turn since he is now willing to do more "illegal" things that the party would disapprove of. It was already bad enough that Winston had wrote down "DOWN WITH BIG BROTHER" in his diary since he was already paranoid with the fact that the Thought Police were after him. If this was causing him issues, why would Winston go and pull something like this? Being rebellious is fine as long as you don't take it too far when you already know what the consequences are going to be.