He was asked to hack Jenna Marshall's phone for the Liars, and later hacked things for Aria, Hanna, Spencer, and Emily. Caleb was the first person, besides Dr. Sullivan to be told about \"A\" and actively worked on decrypting files from A's phone to help Hanna and her friends. In Season 3, he was shot by Lyndon James after finding Emily and Lyndon in the lighthouse at Lighthouse Rock Inn and had to have emergency surgery. He would later make a full recovery.
Hanna and Caleb come home from school and start kissing passionately. They make their way to the kitchen, where Ashley confronts them. She asks Caleb to leave, but Hanna protests that he just arrived. Ashley knows about Caleb hiding in the basement. Ashley evicts Caleb from her home just as he and Hanna were starting to become romantically involved. Caleb leaves, and Hanna follows slamming the door behind them. Two camp out in the woods for the night and they have sex. The next say, Caleb comes over for dinner where Ashley decides to let him stay in their guest bedroom. He steps outside to make a phone call. Caleb his caller know that he is no longer willing to assist them.
The school is having a lock down for its Rosewood High Truth Up Day. Caleb helps comfort Hanna and Aria during their own respective crises. While in the music room the students are told to write something truthful down and that it will be kept anonymous. Jenna refuses saying that people in the school have mistreated her and that it was full of phonies and liars. When Jenna goes to tell Mrs. Hastings on how she was cornered and slap in the girls restroom, Caleb immediately rebuffs that comment saying that if she did tell the truth that she would have to admit she threw the first punch. Later, \"A\" sneaks into the assembly hall where Caleb is sleeping and takes his laptop.
Caleb and Hanna are talking about Mona's locker incident. Hanna suggests that Lucas may be limping after Aria stabbed someone through the box she was locked in on the Halloween train. Caleb says that Lucas haven't been talking much since he revealed that he had lost Caleb's money. At the school's 10k, Aria and Caleb can't believe that everybody has forgotten what Mona was like. Aria asks what it was like to grow up without a dad. Caleb says he would look for him. However, he gave up when he was 13 because he was tired of focusing on someone he never met and started focusing on himself. He does admit, though, that sometimes he does wish that he could meet his dad to replace the person he always imagined with a real person.
Caleb is over at Toby's place. They've put all the information they have about the night of the fire at the Lodge up on a board and are preparing to investigate every lead. Eventually, the two make their way to Howell Acres Flight Center to get more information. Toby and Caleb make up a story and question Nigel Wright. Caleb slips him 40 bucks to show them the flight information. It shows the pilot is named John Smith, leading them to believe it is forged information. Back at Toby's place, they speculate Nigel may have been at the Lodge that night. They return to the flight center to confront Nigel. He says he was paid to fake a flight plan, he wasn't at Thornhill, and after some more prodding, he gives up the name of the person who paid him - CeCe Drake. Nigel runs away, but not before Caleb lifts his phone from his pocket.
Caleb tells Hanna that he tracked down an unpaid cable bill that was sent to the P.O. box in Philadelphia linked with Nigel Wright. The bill is attached to a physical address there, where CeCe may or may not be living. Caleb visits Hanna, and asks if she wants to check out the address in Philly, but she asks if Caleb can help her sneak into Radley. Caleb refuses and they argue about whether Mona is trustworthy or not. Caleb reminds her of everything \"A\" has done. He thinks she should tell the police about \"A\" once and for all because it can't get any worse at this point. Caleb runs into Hanna on the street, and asks what he was doing going into Veronica's office building. He says he doesn't know how to protect her anymore. Hanna asks \"So you were going to tell her!\" He replies yes. He would rather have Hanna hate him and be safe than the other way around, to which she asks if he thinks telling her about \"A\" will keep her safe.
Caleb approaches Hanna at her locker and she tells him she is going shopping with Ali's mom that afternoon. He thinks it's strange, but lets it go and asks what time he should pick her up for the dance. Hanna says they don't have to go, but Caleb informs her that Ashley texted him earlier insisting they go and have fun. Hanna and Caleb arrive at the hoedown, and when Caleb steps away, Hanna is approached by the strange boy, who asks to dance with her. Caleb is weary to trust Travis, but Hanna says that she has to and then she sees Travis leave the hoedown.
Caleb sits on the bus headed for Ravenswood. He is alone except for a mysterious man sitting at the back of the bus and a girl sitting next to him. They make small talk, and she introduces herself as Miranda. She is on her way to Ravenswood as well, and explains that she has been a foster child for most of her life, and she is going to Ravenswood to meet her uncle for the very first time. Caleb mentions that he is a foster child as well. Caleb and Miranda arrive in Ravenswood and say farewell at the graveyard, They again when Miranda and Hanna finally find their way out of the house and go to the graveyard where Caleb was. Caleb finds them, and Hanna tells Caleb that she thinks \"A\" may have Ali. She leads both of them to the tomb where the entrance to the tunnels was, but it is sealed shut. Miranda, meanwhile, finds a gravestone with her name and face on it, and she is baffled. After rejoining the Lairs, Hanna tells Caleb to stay with Miranda to make sure she stays safe. They kiss and bid farewell.
Outside the Cavanaugh house, a second explosion occurs leaving Caleb and the others ducking for cover. At the Brew, Hanna spots Caleb sitting down at one of the tables and walks over to him. Commenting that he looks as if he's got as much sleep as her, Caleb tells her he was with Toby until around an hour ago, and when Hanna asks how Toby is, Caleb says that he's still pretty shaken. Hanna still doesn't understand why 'A' would blow the Cavanaugh house up when they were all a few doors down, and Caleb reminds her, \"A doesn't shoot and miss\". Asking if Hanna's seen the newspaper, he hands it over and Hanna is shocked to find that the police are not looking into what caused the gas leak at the Cavanaugh home, \"the cops in this town should be riding around in clown cars\". When Caleb suggests that the girls should tell the cops everything, Hanna wonders what they could say, they don't have a face or a name. Caleb tells her this isn't a game, \"A blew up a house\", and Hanna says she can't, it'll unravel too much. Telling him that things are not the same as when he left, Caleb tells her he's noticed, and that he won't be staying long, he's thinking of going to Montecito for a while. Hanna says that she just thought if he wasn't in Ravenswood, he would be here, but Caleb doesn't want to commit to anything.
When Caleb asks how good is kind of good, Hanna tells him it was good enough that the guidance counsellor called her in for cheating. As Hanna focuses back on the exit doors, Caleb smirks at her proudly. Caleb and Hanna are still sitting in the car when Aria gets in. Standing by a police vehicle as the Vanderwaal house is taped off as a crime scene, Caleb and Hanna, along with Emily and Paige, and Aria and Ezra, stand huddled together, visibly upset and shaken. Caleb listen on as Detective Holbrook tells the waiting press that while the investigation is ongoing, they have ruled what has happened a homicide and that Mona Vanderwaal was murdered.
He helps Hanna remove stuff from her room while trying to help her move on from her ordeal. He and her mother each try to get her to open up but have little success. Later he lays on Hanna's mattress with her sleeping in his arms.
Toby Cavanaugh - Caleb strikes up a friendship with Toby since they were both trying to figure out who A really is. They find out Nigel Wright was driving the plane together and Caleb even stopped Toby from breaking into a car before the cops came per Spencer's request but he could have refused so because he cared about Toby. And per Hanna (and Spencer's) request, Toby tried to help Caleb overcome his drinking problem and move on from the things that were still haunting him from Ravenswood. 781b155fdc