"Herbert Pocket had a frank and easy way with him that was very taking. I had never seen any of them, and I have have never seen any one since, who more strongly expressed to me, in every look and tone, a natural incapacity to do anything secret and mean(pp 138)." I think Pip meeting Herbert was an extremely monumental thing, because Herbert was Pip's first real friend, someone he could learn from and someone he could confide in. Herbert was also a connection from the past, someone that knew who he was and where he came from. Herbert's character is honest and open, which is refreshing for Pip who's life has so many questions in it at present. As the book goes on, and Pip takes Herbert under his wing and in turn becomes his benefactor, Herbert is not only Pip's friend, but his responsibility in a way.
Whatever my fortunes might have been, I could scarcely have recalled my sister with much tenderness. But I suppose there is a shock of regret which my exist without much tenderness(pp. 218). When Pip's sister dies, it signifies an old part of his life falling away, how he has moved on and how his old life is also moving on without him. I think after Pip spent his whole childhood living under his sister; fearing and hating her, he's surprised at the sadness he feels when she is gone.
Pip has spent basically this entire book so far, in love with Estella, and improving himself so that he can be with her. He has a mislead vision that Ms. Havisham, as his benefactor, has been primping him to be a gentlemen to be with Estella, so when he finds out that Ms. Havisham is in fact, not his benefactor, and does not mean for him to be with Estella, his world is completely shattered.
For a more detailed version of what I just wrote about the end of section two of Pip's life, he is devastated. He's done everything in his life for her, to be be good enough for her, only to basically be spited by having to be her chaperone for her real suitors. Ms. Havisham isn't his benefactor, whilst the convict, a criminal who is in a class even below his own, has been the one supplying his with money the entire time. Pip hasn't been all that great to Pip, because he's constantly worried about what Joe will think about his new life, and how the new people in his life will interpret Joe, he promises to come back and visit more often, but even Pip knows that this is unlikely.