Left at Wardle's, Tupman takes Rachael to a bower and declares his love for her. He is seen kissing her by Joe the Fat Boy. Late that night Wardle and the rest come home from the cricket match hopelessly intoxicated, bringing Jingle with them. Jingle, with his appearance of sobriety, makes a favorable impression on the spinster Rachael. The next day Joe reports Tupman's romance to old Mrs. Wardle, who becomes indignant, and Jingle overhears. Assuming that Rachael has money, Jingle tells her that Tupman is a greedy deceiver. He also tells Tupman that he should ignore Rachael, since he has been discovered, and he borrows ten pounds from Tupman. Thus, Jingle easily replaces Tupman as Rachael's suitor.
A few days later Jingle elopes with Rachael Wardle, and Mr. Wardle is furious. Mr. Pickwick resolves to go along with Wardle to save his sister from an unhappy marriage. After obtaining a chaise, being misled by a bribed gatekeeper, and delayed at an inn in changing horses, they learn that Jingle is directly ahead, so they charge on through the night. They are about to catch Jingle when a wheel falls off their chaise, which puts a temporary halt to the pursuit. Jingle utters some impertinent remarks from his carriage and drives on gaily, while Wardle and Pickwick are forced to walk.
Sam Weller is blacking hoots in the courtyard of the White Hart Inn in London, and Alfred Jingle asks him the way to the Doctors' Commons for a marriage license. Sam then tells him of his father, who was taken in by a marriage license tout and married to a widow that he had no intention of wedding. Jingle purchases the license; Wardle meanwhile arrives at the inn with his lawyer, Mr. Perker, and with Mr. Pickwick. They learn from Sam Weller where Jingle is staying and confront him in the room with Rachael, who tries to throw a fit. Mr. Perker suggests that Wardle compromise with Jingle, since Rachael is over legal age. So, for some 120 pounds, Wardle buys Jingle off. Jingle, on leaving, enrages Mr. Pickwick with an impudent gibe about "Tuppy," and Pickwick hurls an inkstand at him. Mr. Pickwick and Mr. Wardle then return to Manor Farm with the humiliated Rachael.
This section centers on Jingle's blithe rascality in defaming Tupman, courting Rachael Wardle for her money, eloping with her, and accepting Mr. Wardle's bribe of 120 pounds-eight, which Jingle claims is his for his loss of honor and the loss of Rachael!
A number of things take place in these chapters which are of interest. Although Winkle was horror-stricken when he shot Tupman, he comes home drunk that night and says he wishes he had "done for old Tupman" — that is, finished him off, which reminds us that Winkle still holds a grudge against Tupman for loaning Jingle his coat, which involved him in the duel. But the remark foreshadows the fact that things are going to go against Tupman.
Chapter 8 shows Tracy Tupman as a ridiculous lover — ridiculous because his girth and age are inappropriate to the kind of passion he exhibits, which would be fitting in a young stage lover. However, Rachael is equally absurd in her coquetry and in falling for Jingle, who is half her age. The fact that Tupman and Rachael can be tricked by an age-old theatrical ploy on Jingle's part means that their feelings were never very deep, and that Tupman was more interested in romantic posturing than in winning Rachael. As a ladies' man, Tupman is deservedly a failure. Dickens takes love seriously, and Tupman does not: because of this he is the least sympathetic Pickwickian.
Chapter 9, which depicts the pursuit of Jingle, is quite exhilarating to read. Dickens captures the spirit of the chase in a rapid narrative prose punctuated by breathless dialogue and lively yells to urge on the horses. Even Jingle's swift, stenographic gibes add to the effect. Yet Dickens invents — on the fly as it were — a curmudgeonly gatekeeper who comes alive instantaneously in his sly, ill-tempered remark to himself, where we learn Jingle has bribed him.
In Chapter 10, Dickens gives life to two new characters, each of whom plays an important part in the rest of the book: Sam Weller and Mr. Perker, the lawyer. Sam is a cockney "boots" (boot cleaner) with charm, worldly wisdom, a wry wit, and curiosity. Sam, like Dickens, has the power to invest people with life by means of anecdote, and we get an accurate, vital picture of Sam's father, Tony, before he makes his appearance. Mr. Perker is a small, lively man with much caution, since he knows the legal dangers of every situation. But he tends to trip up over his own prudence. When he questions Sam about Jingle's whereabouts he gets nowhere, because Sam is equally adept at verbal equivocation.
Something has happened to Mr. Pickwick's psyche in these chapters: he has lost some of his innocence and learned that not everyone is trustworthy. He has also learned that schemers can profit from wrong-doing. Prior to this the comedy all was farcical, a matter of mishaps and misunderstandings, but, with Mr. Pickwick's new knowledge, the comedy starts to get deeper. Mr. Pickwick is now provided with a motive force to thwart schemers. Jingle's taunt about "Tuppy" was the last straw.