It’s closing time at the Work Bench and Ben and Sock debate the relative merits of Heathcliff vs. Garfield, while Sam closes up. They head for the bar, but Sam finds a dinner jacket in his locker and a sign saying “Put me on.” He does so and finds himself in a posh restaurant where the Devil is having dinner with a Mike Volta. The Devil orders Sam to sit with them and Mike tells stories about all the wives he’s had affairs with. When the man at the next table proposes to his girlfriend, the Devil dares Mike to have sex with her. Mike takes the challenge, but as soon as he’s gone the Devil tells Sam to take the vessel under the table and send Mike back to Hell. Mike invited the Devil to dinner, hoping to charm his way out of Hell. Sam interrupts Mike in the cloak room and after the girl leaves, Sam uses the new vessel, a Kodak instant camera, and captures Mike.
The next day, Sam goes to the DMB with Andi, who isn’t happy with the situation and insists on trying to find a way for Sam to get out of the contract. They drop off the vessel and Sam introduces Andi to Gladys.
Meanwhile, Sara gets to Ben one step ahead of an immigration office, Agent Papelbon, and kisses Ben to make it appear they’re married. Papelbon isn’t impressed and tells them to come in for an interview so he can verify their marriage.
The Devil finds Sam and moves a ladder out from under him to leaving him hanging. He’s angry, noting that Mike has escaped Hell already. The Devil gets him back to the ground and apologizes, saying he’s mad that Mike can get out of Hell. He figures there’s a mole and he will find out who it is.
He then directs Sam to a mailbox holding the vessel. Sam takes it and finds himself teleported to a suburban home, the Carvers. Mike sneaks out the window as the husband James arrives home. Sam confronts him and Mike doesn’t put up a fight, but warns that he’s just going to get out of Hell again. Sam has no choice but they pose for the picture as Mike goes back to Hell. Sam drops off the vessel but stays to watch her put it in the delivery tube. Once he’s gone, she recovers the vessel and puts it in her purse.
Tony comes by the Work Bench to make sure that Sam is okay since the Devil is on the warpath. Andi asks Tony if he can help Sam get out of his contract and Tony agrees to do what he can. Sam offers to get the contract from his father and get it to Tony.
Sock goes over the fake photo album that Sara and Ben have put together. Sock isn’t impressed and notes they need photos of them having sex to convince and distract the agent. Sara already has some and convinces Ben to go along with it.
Sam is heading up to his condo when Mike confronts him in the elevator and invites him to go out to Club Rendezvous that night so they can pick up chicks. Mike figures the Devil is jealous of the fact they’re enjoying themselves. Sam warns him that he’ll still have to catch him when he gets the vessel back. Sam then goes to his apartment to find the Devil drinking a pina colada and congratulating himself on having recovered Mike. Sam gives him the bad news and the Devil is angry, admitting it’s a matter of respect. The Devil then shows Sam exactly what damage he does: he takes Sam back to the Carver house and shows him that James Carver shot his wife and then himself. The Devil gives Sam the vessel again and tells him there’s no more excuses.
Ben and Sara meet with Agent Papelbon who isn’t too impressed by the photo album. He then asks Sara and Ben some questions and it doesn’t go well. He tells them that on Monday Sara is being sent back to Manchester and Ben is going to jail.
That night, Sock and Andi wait for Sam while he gets the contract before they try to find Mike at the club. Sock provides hair and fashion tips, although Andi isn’t too thrilled. Mr. Oliver reluctantly gives up the contract and on their way they call Ben, who is drunk.
When they get there he greets them and starts running down the street, ripping off his shirt. He figures since he’s going to jail on Monday he’s going to go out in style. Behind the club, they spot Mike escaping another jealous husband… with Gladys as his getaway driver. They follow the car back to Gladys’ house and find him keeping her company. He grabs a knife and threatens Gladys, but Sock just laughs it off, saying he picked someone they don’t care about.
Mike stabs Gladys through the heart and runs off, and they determine Gladys is dead. They take Gladys out to the car where Ben is passed out drunk.
Sam figures they should go to Tony for help. Tony isn’t home so they go out in the woods and dig a grave. Meanwhile, Ben wakes up to Gladys’ dead body and sobers up. Tony spots them and flies down in his demon form, and offers his help, promising Sam they’ll figure a way to get him out of his contract. Sock gives a brief eulogy until Tony realizes Gladys is a demon, and takes the knife out. Fortunately, Demon’s can be killed by mortal weapons. Gladys comes back to life… and starts throttling Sock.
Everyone heads to the bar where Gladys drinks two pitchers of beer. Sam tries to warn her but she says she can take care of herself and refuses to give Mike up. Andi gets her to explain that she just got tired of being lonely. The next day at the DMV, the Devil arrives to confront her.
The next day, Josie provides legal advice to Ben and advises him to pay the fine rather than go to jail. He only has $2,000 and she advises him to borrow the rest, but Sara is going to be deported no matter what. Ben gives her the news but she reveals that she’s set it up to bribe Papelbon but she needs all of Ben’s money along with her own. She turns on the charm and he agrees.
Gladys arrives at the store and tells Andi and Sam where Mike might be at: a church where a wedding is being held. She admits that Sam was nicer to her than Mike, and asks Sam to watch her cat. She says the Devil is reassigning her to the head office. Andi is concerned and suggests Sam talk to the Devil, but Sam warns that asking for a favor is a bad idea. he figures she’ll be fine… until a giant worm swallows Gladys.
The guys go to the church where Andi is in fancy dress. She gets in but the usher turns them away, so they split up to find another entrance. Sam goes to a basement entrance and gets in when the bridesmaids look for the bride. Sam finds the bride hiding… and Mike underneath her dress. He flees to a nearby basement and hides, noting Sam can’t take a photo without a flash and he’s only got a few flashes left. Sam runs them out and Mike attacks him as Sam makes a break for the door. Fortunately, Sock and Ben arrive, opening the door and letting in the light, and Sam gets his picture… and his soul.
Later, Sara calls Ben to let him know that she’s going on the lam, with his $2,000. Meanwhile, Tony goes over the contract with his fellow demon, Kenneth. Kenneth informs him that someone has removed every page that references Sam’s real father. They both seem to know who Sam’s real father is.
Cassidy is happy that Ben won’t be “married” any more, but it turns out that Sam is only going to jail for eight days. Sock gives him a going away present: a punch to the face so he isn’t so attractive in jail. Ben understands.
Sam runs into the Devil in the parking lot, and the Devil congratulates him for his fine work. Sam asks him to let Gladys go, suggesting it might be good for employee morale. The Devil isn’t buying it, but Sam asks him “Please.” Surprisingly, the Devil gives in and returns the stunned Gladys to Earth, then offers Sam some turkey jerky. Meanwhile, Tony and Kenneth watch them and Kenneth notes that somehow Sam got the Devil to spare a demon. He also notes that the Devil spared Sam during the rebellion. Tony finally admits it’s true: Sam is the son of the Devil.