Caleb and Aria seem to get along as friends after he starts helping the girls track down "A".
In Monsters in the End, after Hanna and Caleb's breakup, Caleb went over to Aria to get her to give him advice on how to get back together with Hanna. While Aria refuses to help him, Ella Montgomery walks by and assumes that Caleb is her boyfriend and mouths that he's cute. Aria shakes her head and then leaves Caleb, who seems to have lost hope to ever get back together with Hanna.
In She's Better Now, they talk about Mona's return to Rosewood High, and Aria asks about his family life. Caleb seems to open up a little to her.
In The Naked Truth, Aria and Caleb arrive into the music room, where Jenna is there. When Aria gets up to leave, Caleb tells her that she doesn't have a choice to miss Truth Up day, and that if people are spilling their guts, they might have some interesting things to say. Aria agrees with him. When Hanna can't find Caleb after he last talked to Jenna, Aria goes around asking people where he is even asking Noel and Jenna.
In She's Better Now Caleb opens up to Aria about his father and how he use to look for him everywhere.
In Grave New World, it is Aria that asks Hanna where Caleb is.
When Caleb returns to Rosewood in Who's In The Box?, Aria notices him and smiles when he and Hanna kiss. Aria is upset when Hanna tells the girls he left Rosewood and went back to Ravenswood after breaking up with her.
In Through a Glass, Darkly Aria seeks out Caleb in hopes he can help her to see why she got rejected from her chosen college, as Aria thinks A is behind it. Caleb then goes on to teach Aria about hacking on Mona's laptop.
In Hold Your Piece Caleb teaches Aria how to hack into computers and know their data. Aria uses these skills to hack into Sydney Driscoll's Device. It also shown that Aria might have had very little technological knowledge in high school. It might've took time and been difficult for Caleb to teach Aria but yet he worked it. It is not clearly specified that Caleb was doing this just for letting Aria hack into Sydney Driscoll's Device our doing it for Aria herself.
- Aria and Caleb both have an on-and-off again relationship with their exes.
- Both have opened up to Jenna at one point in the series.