When Pip tells Biddy that he wants to be a gentleman, she tells him straighforwardly that she doesn't think it is a good idea. She says, "I wouldn't if I was you...I don't think it would answer". Biddy is afraid that if Pip were to attain his goal of becoming a gentleman, he would not be satisfied. She asks him, "don't you think you are happier as you are?"
Pip responds to Biddy that he is not at all happy as he is; in fact, he is "disgusted with (his) calling and with (his) life". Biddy is sorry for Pip, and comments that his dissatisfaction is "a pity". She tells him that she only wants for him "to do well, and be comfortable".
Biddy asks Pip why he wants so badly to be a gentleman, and when he tells her it is because of what Estella said to him, she suggests gently that perhaps someone who would be so cruel as to make him feel ashamed of his station in life is not worth changing for. Biddy, who fondly remembers that she was Pip's "first teacher", is an honest and perceptive young lady, and she is kind and decent in advising Pip even though he is blunt and tactless with her, so wrapped up in himself that he is oblivious of her feelings for him. Deep down inside, Pip knows that he would be much better off being satisfied with himself the way he is, and courting someone genuine and loving like Biddy. He is aware that even if he gains Estlla's approval, she will always make him miserable, yet he feels compelled to pursue her (Chapter 17).