Both sought favor in the eyes of Estella and Havisham and felt the failure of being men. That's all it took to lose face in Satis House.
Both have GREAT EXPECTATIONS and no honest savings behind those expectations.
Both get funds from a benefactor for a time: Pip, Magwitch, and later, Herbert, Havisham.
Both operate with their benefactor anonymously through a manager.
Herbert has been raised in privilege to a degree. He at least has education and background. Pip has very little gentlemen in him until he learns how to have it.
Pip has great passion and desire, Herbert goes throughout life with a very even-keel attitude.
Two young, unworldly men, although from different environments, Pip and Herbert both do not know how to manage their lives.
Both Herbert and Pip have never lived on their own before they become roommates. They have no idea how to budget their allowances, and they both get into financial difficulties.
Both Pip and Herbert, who are near the same age, are under the tutelage of Matthew Pocket.
Both Pip and Herbert disapprove of Estella's manner and attitude.
Both struggle to become educated, succeed in life, and find a profession.
Herbert is a relative of Miss Havisham's and is from an upper class family. Pip, as Estella calls him, is "common," or from the laboring class.
Miss Havisham sent for Herbert when he was younger "on a trial visit," but she did not approve of Herbert. When she sent for Pip, he was told to return to play with Estella.
Pip describes Herbert as a person who has "a natural incapacity to do anything secret and mean." This is unlike Pip, who is cruel to Joe when he comes to London to visit Pip in Chapter 27.
Herbert has a sanguine nature; Pip broods at times and is judgmental and snobbish as he stays at the Blue Boar rather than visiting the forge. He argues with Biddy about Joe in Chapter 19; he displays his repulsion for Magwitch who returns to London and tells Pip he is the young man's benefactor.
Pip becomes aware of the vicissitudes of life and of Herbert's unrealistic hopes and attitudes. He arranges with Miss Havisham for Herbert to obtain a position so that he can afford to marry, but Herbert has no idea that Pip has done this and believes that he has secured the job on his own.
Pip believes that "clothes make the man" and along with money, he can become a gentleman; Herbert is truly a gentleman as he is mannerly and of a kind and polite disposition.