When Herbert and Pip first become roommates, in his great desire to become a gentleman, Pip asks Herbert if he will teach him table manners. Herbert politely replies, "With pleasure...though I venture to prophesy that you'll want [need] very few hints. Will you begin at once to call me by my Christian name, Herbert?" Herbert wishes to put Pip at ease by complimenting him, giving him some confidence, and putting them on an equal plane by calling him by his first name. These gestures are those of one who wishes to be a friend.
Pip describes Herbert as "so unassuming that I felt grateful to him for not being puffed up. It was a pleasnt addition to his naturall pleasant ways, and we got on famously." Even when Joe comes to visit and Pip is embarrassed by his awkward behavior, Herbert, a true gentleman, eases the tension by acting the gracious host to Joe. He even goes so far as to aid Pip in helping the convict Magwitch escape. Tolerant, fair, and loyal, Herbert always tries to ease Pip's discomfiture--a true friend.
The best example of the friendship between Herbert and Pip is when Pip secretly sets Herbert up in business. Pip also tells Miss Havisham that Herbert and his father are good people and should not be lumped together with the rest of the Pocket family. Pip even asks Miss Havisham to help Herbert without Herbert knowing about it. Once Miss Havisham agrees and sends some money for Herbert, Pip says, “I had the great satisfaction of concluding that arrangement. It was the only good thing I had done, and the only completed thing I had done, since I was first apprised of my great expectations." Herbert then helps Pip hide Provis (Magwich) and when all of Pip's money is gone, Herbert hires Pip and they remain life-long friends.