In Careful What U Wish 4, Caleb takes Emily's phone to help enable her to talk to Maya, who is at True North. Later, in that same episode, Emily requests him to fix her phone problem quickly, and gives him $40.
When Emily asks a question about Caleb's family life, Caleb offers to tell her his life story for a some food. Emily then gives him a weird look and then walks away.
In The Lady Killer, after killing Lyndon James, Emily immediately falls into Caleb's arms, who has just arrived. Lyndon, who is barely alive, manages to shoot Caleb with a gun.
In She's Better Now, Caleb seems to have recovered, and in the beginning of the episode, at the Brew, Emily is talking to Aria, Spencer, and Hanna, and Caleb appears. When Caleb heads towards the group, Emily says she has to get back to work. Caleb follows her, telling her to feed him.
In Taking This One to the Grave, Emily, Paige, Hanna and Caleb are decorating the front lawn of Emily's house with Christmas decorations. As Emily puts a porcelain Jesus in a crib, Caleb asks her why she loves Christmas so much and she states that it is always when her father comes home.