Sam, Ben and Sock encounter a few surprises on their return from a road trip; Andi refuses to speak to Sam; the Devil has a new assignment.

Sam wants to find out how Alan got out of his deal with the devil, but after they are attacked by two demons, Alan disappears and a demon takes an interest in Ben.

Sam must capture a former boxer by using boxing gloves as a vessel. Meanwhile, Andi is awarded a promotion at the Work Bench.

Morgan tells Andi that Sam is the Devil's son. An escaped soul leaves her baby behind, causing Sam, Sock, and Ben to turn to Tony for help.

The Devil misleads Sam into thinking his next escaped soul is an easy catch and encourages him to take along the gang for a road trip. Unfortunately, when they arrive, they discover a tentacled beast has taken over a small town and is eyeing each of them as its next dinner. Meanwhile, Andi feels Sam is becoming too comfortable with this lifestyle, Ben struggles to not be so clingy with Nina, and Sock makes one last effort to sleep with his stepsister.

The devil wants Morgan and Sam to spend more time together; Sam tries to get Andi back.

Sam and Alan make a deal; Morgan and Sam are pitted against each other; Nina wants Ben to introduce her to his family.

The Devil sends Sam to a tutor for proper training to be the Devil's right hand. Sam uses this as an opportunity to get information about the Devil in hopes of getting out of his contract.

Sam takes pity on Morgan, who has fallen on hard times since being disowned by the Devil, and lets his half-brother move in, cramping the guys' style.

Sam, Sock, and Ben go after their old high school teacher, Mr. Sprong, assuming he is the current soul they are trying to catch. The only problem? Mr. Sprong is still alive, and none too happy when the boys take him hostage to try to convince him not to press charges.

Sam gets into a confrontation in his new job that ends badly. Sock tries to date a demon who has the ability to be anything he desires.

When Nina returns from Hell with the information Sam needs, he challenges the Devil to the game he's best at. However, when it comes to a draw, Andi is forced to make the ultimate sacrifice.