The next Sunday afternoon, Pip goes to Walworth to hear Wemmick's "Walworth sentiments." While waiting for Wemmick to return home from his walk, Pip learns from the Aged that the Aged used to work in warehousing in Liverpool and London and that he had raised Wemmick to go into wine-coopering, not law. Wemmick returns from his walk with Miss Skiffins, a lady Wemmick is courting.
An insight into Wemmick's social class background. His father was a manual laborer and planned for Wemmick to be the same (a wine cooper is someone who bottles and sells wine), but Wemmick has risen to be an office worker.
Pip and Wemmick stroll around the property to discuss Pip's question. Pip describes his wish to invest in Herbert's future as if he has never mentioned the idea before and fills Wemmick in on the personal details of Herbert's life. Pip explains that he wants to plan the investment secretly so that Herbert will not realize he has received any assistance. Wemmick responds by commending Pip's kindness and agreeing to carry out the plan with the help of Miss Skiffins' brother, an accountant.
Pip's desire to give anonymously proves he isn't merely being generous to enhance his own reputation. Wemmick's Walworth personality permits him to praise Pip's kindness—in the office Wemmick could only ever praise business savvy.
Pip stays at the castle for a cozy tea with Wemmick, Miss Skiffins, and the Aged. Throughout teatime, Wemmick periodically tries to slide his arm around Miss Skiffins' waist but she calmly unwinds his arm each time and lays it back on the table.
Miss Skiffins and Wemmick are courting but not married, and Miss Skiffins protects her reputation as a wholesome woman by refusing to let Wemmick touch her waist.
Wemmick carries out Pip's plan, meeting with him again several times at Walworth and in London (though never in or near Little Britain). They arrange for a merchant's house called Clarriker & Co. to offer Herbert work. Herbert, not knowing that he owes his job to Pip's secret investment, is ecstatic. Pip is teary with happiness, overjoyed to think that his "expectations had done some good to somebody."
Pip's generosity towards Herbert has not only improved Herbert's life, it has also improved Pip's own character and given Pip joy. It is the first wholly unselfish action Pip has undertaken since he came into money.