Pip and Herbert Pocket are alike because both are young men learning to be gentlemen.
Pip and Herbert met at Miss Havisham’s house on her birthday. Herbert forced Pip to fight him, causing him a great deal of grief. At the time, Pip knew Herbert only as the “pale young gentleman” and lived in fear that he would tell on him. The two are students of Herbert’s father, Mathew Pocket. They room together as they learn to be gentlemen. Both have expectations, but neither really have an easy time becoming gentlemen. While Herbert grew up knowing he would become a gentleman, he doesn’t have the money for it. Pip has the money but not the manners. Herbert plans to have the money someday, spending his time looking about him.
Yet, having already made his fortune in his own mind, he was so unassuming with it that I felt quite grateful to him for not being puffed up. It was a pleasant addition to his naturally pleasant ways, and we got on famously. (Ch. 22)
Pip and Herbert help each other. Herbert explains to Pip how to behave as a gentleman, and Pip funds their lavish lifestyle while the two of them take on debts that only Pip can even hope of paying back, since he is the one with the secret benefactor.
Although Herbert comes from a family of gentlemen, you will notice that his family does not have money. His father married "the only daughter of a certain
quite accidental deceased Knight" (Ch. 23), and like Pip he elevated himself and did not elevate himself at the same time. She was not really a noble, because the title came without money but she was raised expecting it. As a result, she was fairly worthless. Matthew Pocket was nice enough, but also fairly worthless as a father.
Herbert and Pip are both dreamers. They are both gullible, and both kindhearted. Their biggest problem is that they are pawns in other people’s games and fantasies. Miss Havisham and Magwitch use them to their own ends. Herbert escapes undamaged because Pip uses his money to pay for a partnership for him so he can marry Clara. Eventually, Pip himself realizes the mistakes he has made and understands that good friends and true love are more important than wealth, power, and ambition.