The first time Dill meets Jem and Scout is described in chapter 1 of the novel. Jem and Scout are playing in their back yard when they hear something next door. Expecting to perhaps find a puppy, they instead find a small boy, who we soon know as Dill, "sitting looking at (them)." The children introduce themselves, and Dill tells Jem and Scout that he is from Mississippi but would from now on be spending every summer with his aunt in Maycomb County. Dill also shares with Jem and Scout the information that his mother had "entered his picture in a Beautiful Child contest and won five dollars." Dill says that his mother gave all of the money to him and that he used it to go to the cinema "twenty times." Jem and Scout are immediately impressed by this because in Maycomb County, where they live, they don't have any "picture shows … except Jesus ones in the courthouse sometimes."

The most impressive information that Dill shares with Jem and Scout is that he has been to see the film Dracula. This is a revelation which "move(s) Jem to eye him with the beginning of respect." Dill tells Jem and Scout all about the film, and in the process he demonstrates that he is an excellent story-teller. This proves to be the first of many stories that Dill, Jem, and Scout will share with one another every summer. Indeed Dill proves to be, as Scout puts it, "a pocket Merlin, whose head teemed with eccentric plans, strange longings, and quaint fancies." Soon after, of course, Dill is the one who becomes most fascinated with the strange stories about the Radley Place.