Towards the end of Chapter 1, Dill bets Jem "The Gray Ghost against two Tom Swifts" that Jem will not knock on the Radley door. Jem is extremely afraid of awakening the malevolent Boo Radley and makes several excuses as to why he cannot knock on the door. Jem tells Dill that Boo will more than likely chase him out of the yard and end up killing him. Despite Jem's insistence that Boo would murder him if he carried out the bet, Dill continues to criticize Jem for stalling. After contemplating for several days, Jem reasons with Dill to simply slap the side of the house instead of knocking on the door. Dill accepts the bet, and Jem ends up slapping the side of the house. After Jem slaps the Radley home, he bolts out of their yard, and the children follow him back to Atticus' porch. Scout mentions that as they stared at the Radley home, they thought they could see an inside shutter move slightly.
At the very beginning of To Kill a Mockingbird, Dill dare's Jem to touch the side of Boo Radley's house (in an attempt to make him come out). It all begins when Dill wonders what Boo really looks like and if they could make him appear. "Our first raid came to pass only because Dill bet Jem The Gray Ghost against two Tom Swifts that Jem wouldn't get any farther than the Radley gate. In all his life, Jem had never declined a dare" (13). Jem considers the dare for three days until Dill gets a bit more specific about it. "I won't say you aran out on a dare an' I'll swap you The Gray Ghost if you just go up and touch the house" (14). Jem not only accepts the dare, but succeeds. After the kids return, panting, they simply think they see one of the Radley's inside shutters move. This is the dare that begins it all and sets Jem and Scout on the journey that will eventually lead them to understand and love our dear and misunderstood Boo Radley.
Dill dare's Jem to touch the side of Boo Radley's house