Jem walks in Boo Radley’s shoes when he realizes that Boo is just a gentle and shy man looking for a friend.
At the beginning of the novel, Jem has a very unsophisticated view of Boo Radley. Like the other children and neighbors, he describes him as a legend and joke. His “reasonable description” involves Boo being “six and a half feet tall,” amongst other details.
[He] dined on raw squirrels and any cats he could catch … There was a long jagged scar that ran across his face; what teeth he had were yellow and rotten; his eyes popped, and he drooled most of the time. (ch 1)
Jem’s childhood consisted mostly of running past the Radley house, avoiding the nuts that fell over the fence from the trees, and being dared to touch the house. Dill, Scout, and Jem act out Boo’s story with childish embellishments. Yet once he gets a little older, he starts to try to understand Boo. The children even try to leave a note to tell Boo it’s ok to come out.
When Boo begins leaving gifts for the children in the tree, they do not know who they are from at first. Yet Jem makes the connection.
A turning point for Jem is when he loses his pants on the Radley porch. Jem returns to find his pants inexpertly mended, obviously by Boo. Jem is impressed that Boo did not want him to get in trouble.
When Scout finds a blanket on her shoulders at Miss Maudie’s fire, Jem pleads with Atticus not to return it.
Jem seemed to have lost his mind. He began pouring out our secrets right and left in total disregard for my safety if not for his own, omitting nothing, knot-hole, pants and all. (ch 8)
This demonstrates Jem’s maturity and ability to walk in Boo’s shoes. He sees him as a lonely, quiet, shy man to be pitied rather than a monster. Boo became a friend.