|“||You ready to do this?||”|
— Toby to Caleb
In "Crash and Burn, Girl!," Caleb and Toby are shown in Toby's apartment investigating the murder of Darren Wilden and trying to figure out how Red Coat landed and who she is. They visit Howel Acres Flight Center and Nigel Wright covers up the story. Caleb bribes Nigel and he shows them a doctored flight plan from the night of the fire. The flight plan shows both of them that the plane landed in Delaware, had no passengers, and was piloted by a "John Smith". Caleb asks whether or not the plane could stop in Thornhill that night, and Nigel replies that it could've, but likely didn't inform Air Traffic Control. Nigel then goes on to say that it was foggy that night and it was unlikely that someone would've landed there. Toby informs Caleb later that night, in the loft, that Nigel's statement bothers him, as there was no way of Nigel knowing that it would be foggy unless he was there. Toby then realizes that the NW on the lighter may be Nigel's initials, and the two go back to question him the next day. Toby and Caleb then accuse him of flying the blonde to Thornhill and faking the flight plan. Nigel claims he didn't know about the fire, but was paid by CeCe Drake to make a fake flight plan. When prompted further, he throws the money at Toby, pushing both of them, and runs away. Toby begins to run after him, but Caleb tells him to stop. He then reveals that he took Nigel's phone and later, while accompanied by Spencer and Toby, hacks into his phone. He sees that Nigel made seventeen phone calls to a number in Manhattan, whom they all assume belonged to Cece.
In "Bring Down the Hoe,", when Spencer asks Caleb to go after Toby, he agrees to follow him. Caleb finds Toby at Dr. Palmer's car trying to break in, and he tries to stop him. Toby doesn't listen and continues to try to break into it. Caleb tells him that he needs to stop listening to -A. Then, sirens are heard, and they both realize that this was a set-up by -A. Toby and Caleb sprint off and away from the police.
In "Now You See Me, Now You Don't," Toby and Caleb wait outside Mona’s house, noting that her parents are out of town. Caleb goes home while Toby stays.
In "No One Here Can Love or Understand Me", Spencer convinces Toby to go on a double date with Hanna and Caleb so that he can talk to Caleb about his drinking and sleeping problems. Toby asks Caleb to deal with his problems. Caleb states Toby does not know his problems which Toby responds that he does as he had been to Ravenswood too. Caleb states that he lived there while Toby was a tourist and that Toby was crossing a serious line. Toby further questions Caleb which causes Caleb to storm out of the Grille.