Herbert Pocket, Jr. is Pip's roomate in college and his best friend. Herbert is not terribly bright, but he is an extremely kind person and a loyal friend. Herbert is unquestioningly generous; when he comes into an unexpected fortune, he expansively offers to share it with Pip, and, at the end of the story, when Pip is left destitute, he kindly offers him a job. Herbert's patience and gentle demeanor extends even to the difficult alcoholic Mr. Barley, and, happily, he ends up marrying Mr. Barley's daughter Clara, a woman who is as kind and good-natured as he is. Herbert Pocket's even, easy-going personality is a stark contrast to Pip's driven, acquisitive one; he remains constant through his ups and downs in fortune, while Pip is much more mercurial.
There is another Herbert Pocket in the story, the young Herbert's father, Herbert Pocket, Sr. The elder Pocket is a teacher, albeit an inadequate one; he works at his trade not out of love for what he does, but so that he can keep his wife and children fed. Despite his ineptness, Herbert Pocket's household is a welcoming place, and his son and his friends often gather at his home.