Herbert is Pip’s best friend. The two first meet when they are little boys at Miss Havisham’s house. Herbert challenges Pip to a gentlemanly fight (there are rules and everything), which Pip easily wins. As luck would have it, many years late they become roommates in London and, they have a great time together. Herbert shows Pip the London ropes and helps him learn how to become a gentleman. If left to his own devices, Herbert lives a simple, frugal life. However, under Pip’s influence, he starts spending more money than he owns and goes to parties and things. Though Pip doesn’t feel like Herbert will ever be very successful in life, he loves his idealistic attitude. Herbert wants to be an insurer of ships. He falls in love and eventually marries Clara Barley, a ship purser’s daughter, and they move to Cairo with Pip.