Caleb Rivers is better known the the "computer guy" at Rosewood, at first he fixed Emily's phone for her and chargers her an extra $40 for a rush job because she needs it. Overtime they start to bump into each other more in the hallways at school. They both end up in detention where Hanna does not want to be because "A" forced Hanna to give Aria's mother a ticket to a art show where Aria and Ezra would be on a date. Caleb sneakily emails himself but it looks like it came from his social workers and he is dismissed from detention. He did this so that he could go to Aria's mother car and take a piece from it so that it would not start and she could not make the show therefore keeping Aria and Ezra's relationship a secret.

To repay Caleb back for doing that, he wants to use Hanna's popularity at school so that he gets more customers to fix things and gets more money and of course she does this. Later then Hanna finds him sleeping in the school because Caleb and his foster parents do not get a long. Hanna decides to invite him to stay at her house without telling her mother, he will be staying in the basement. Over time, Ashley starts to realise something is up because they are eating more than ever and it was nearly a close call when Caleb was taking a shower and Hanna walked into the bathroom to grab her mascara and Hanna's mother needed something from the bathroom as well. In order to hide Caleb, Hanna jumped in the shower with him and covers his mouth to prevent him making any noise whilst her mother was getting her charger outside the shower. This is a funny awkward situation, Caleb turns around for a second and when he turns back, he catches Hanna having a sneak peak.
Ever since that situation, Hanna has been avoiding Caleb and this makes him think that she does not want to speak to him or let him stay at her house anymore, therefore he starts to pack his things. This is not the case though, Hanna finally tells Caleb how she feels and they end up kissing which leads to them making out and secretly dating but one night, Hanna's mom walks in on them making out and she orders him to move out.

Caleb turns up at the carnival to deliver Hanna the letter but Hanna spots him first and tells Mona to say that she is not here and Hanna runs off. Caleb talks to Mona and asks her to give Hanna the letter but Mona gives him a speech about how much her has hurt Hanna and she does not want to speak to him, Caleb walks away so that he can make the bus out of Rosewood. We all thought that Mona would give Hanna the letter, but we are wrong, she reads it and then upset and angry at what Caleb has written, she throws it in the bin and Hanna is completely oblivious. During this moment, the camera pans down the the bin and we can see written on the letter that Caleb wants Hanna to call him and that he loves her.
Later on, Hanna spots Caleb in the line for the bus out of Rosewood and Aria forces her to go and speak to him but Caleb spots her and looks at her but because Hanna has not read the letter she does not know how he feels about her. Hanna does actually consider going to talk to him but she thinks about it and walks away refusing to, Caleb gets on the bus and leaves.