At the Work Bench, Sam, Sock, and Ben are discussing Sock wanting to get rid of his cell phone. As Sam leaves on his own, he finds Morgan teleported into his car, and his car teleported to the docks. Morgan and Sam start arguing and the Devil arrives to tell them to take it easy. He tells them they need to step up and prove one of them is suitable to be his second-in-command. The Devil gives them both a fire extinguisher vessel and tells them that whoever brings back the most recent escaped soul will serve as his right-hand man, and the loser will be cast out.
Back at the Work Bench, Morgan tells Sam that he plans to win and Sam agrees. He offers his help but Morgan doesn't believe him. Meanwhile, Sock and Ben arrive at Sock's house and find Ben's grandmother there. Sock starts to explain that Ben is dating Nina but Ben hastily claims Nina is his personal shopper and tries to distract his grandmother. She calls her dog Chico and leaves. Once she's gone, Ben warns Sock that his grandmother can sense evil and would disown him if she found out.
Andi hires her newest employee, the elderly Pesi, and then meets with Sam to tell him he has the day off to go to the cemetery to look for Alan. Sam is skeptical that Alan will help but Andi says it's worth a shot. She suggests they crash a funeral to get in. Once they arrive, they split up and Sock infiltrates the funeral. He spots an attractive blonde woman, Olivia, who is there to mourn the death of her high school teacher. Sock claims to be a student as well and Olivia invites him to a candlelight vigil later.
Sam spots Alan and gives chase. Andi and Ben manage to intercept and tackle him. They fight it out near the funeral and Sock tells the priest to continue. Finally he gets over to where the others are trying to force Alan to talk. They take Alan to the tracks and Sock explains that Alan used to be a gambler, and if he gambles even once he goes back to Hell immediately. Sock and Ben start to pressure him but Andi has second thoughts and Sam tells them to stop. They go back to the cemetery and Alan explains that he has to stay off the Devil's radar. However, he's not thrilled with living full-time on sacred ground.
Nina visits Ben and invites him on a date, but Ben explains he's going to his cousin's confirmation. She thinks it sounds like fun but Ben believes it's a bad idea. He explains about his grandmother and refuses to stand up to her. His grandmother arrives outside and Ben asks Nina to wait for him and they'll talk later. However, Nina comes out with him, insisting his grandmother will love her. She introduces herself but Ben's grandmother tells Ben to keep Nina away from her, then spits on the ground.
Morgan visits Sam at the Work Bench and asks for help, admitting he's having trouble. He hands over the file on the soul, Bud Brown, who has a chop shop near the pier. It turns out Morgan hasn't done anything. They go to the chop shop where Bud is working on some elaborate project. Morgan switches his fire extinguisher for Sam's. Sam offers to go in, capture Bud, then give the vessel to Morgan to turn in. Sam confronts Bud and sprays him with the fire extinguisher, but nothing happens. Bud goes for a nail gun but Sam manages to disarm him and grab the gun. He shoots Bud several times until the escaped soul flees. Outside, Sam confronts Morgan, who admits he gave Sam a real fire extinguisher to eliminate the competition. Sam insists he doesn't want to win but Morgan still doesn't believe him.
Back at the Work Bench, Sam tells the others what happened. He figures if the Devil is stuck with the lazy Morgan, the world is better off. The guys reveal that they've came up with an idea to help Alan: they get him to a city built on consecrated ground. They go back to the cemetery and show Alan a film of how fun life is in Vatican City. Alan, convinced, agrees to tell Sam how to get out of his deal in return for sanctuary.
That night, Sock goes to the candlelight vigil and suggests to Olivia that they go bowling to overcome their grief. Olivia notes that the dead teacher, Mrs. Simons liked to bowl. She mentions there's an intimate memorial service on Thursday, and they can go bowling after that.
Ben's grandmother is working on the garden at Sock's house when Nina comes to see her on her own. She explains that she's not evil and was once a fallen angel. Ben's grandmother is impressed that Nina has met St. Peter. However, Ben sees them and thinks something is going wrong. He runs out but Chico comes out and startles Nina, who transforms to her demon form. Ben's grandmother collapses from a heart attack.
Later, Ben returns from the hospital to tell the guys his grandmother will recover in a few days. He's not happy that Nina ignored her but isn't sure what to do. Sock is dressed for the funeral and boasts he should be getting some tongue action. Ben leaves for the hospital. That night, Sock goes to the memorial and talks to Olivia, who is convinced she should put her teacher's death behind her. Then she introduces Nate, her boyfriend, and asks Sock to help Nate talk through his grief. Sock prepares to make a hasty exist, until Mrs. Simon's lawyer announces that Mrs. Simon left $10,000 to each student to donate to charity. Sock makes a hasty return.
Sam is trying to make travel arrangements for Alan when the Devil teleports him to a diner and tells him and Morgan how disappointed he is in both of them. He reveals that Bud is working on a portal to allow his buddies to escape from Hell. The Devil disappears and Morgan admits he's disappointed that the Devil doesn't respect him. Sam is surprised but Morgan insists he just wants to make his father happy. Sam finally convinces Morgan that he's sincere and they need to work together.
Sam and Morgan return to the chop shop but Bud has already completed the portal. Two escaped souls come through and a fight breaks out. Morgan's vessel only works on Bud, so Sam attacks the other two, knocking one back into the portal. The other one strangles Sam while Morgan tries to deal with Bud. Bud throws the vessel into the portal and Sam tells Morgan to run. Bud knocks out Morgan while Sam throws the second soul back through the portal. Bud prepares to kill Sam but Morgan grabs him and holds him off long enough for Sam to shove Bud into the portal. Morgan points out that Sam is the one who sent Bud back, but Sam says that he'll lie. Morgan's good with that.
Sock and Ben meet with Mrs. Simon's lawyer and Ben pretends to run a non-profit organization. Ben explains that he's a scientist creating a self-sucking straw, the straw-o-matic. The lawyer is satisfied and gives them the money. Back at home, Sock is impressed with Ben's idea and wants to use the $10,000 to build a prototype. However, they discover that Alan wants more money to cover his expenses. Sock and Ben slip out to discuss the matter and wonder if they should help Sam. However, Sam finds the money and they have no choice but to give it to him.
As Sam takes the money and goes to find Alan, he finds himself teleported to a bar where the Devil offers his congratulations. The Devil knows what happened and refuses to believe Sam's lies. Morgan arrives and the Devil tells him that he's lost everything but $10 and a bus pass. Morgan vows revenge on Sam and leaves.
As Alan prepares to leave for Vatican City, he tells Sam that he can get out of the deal by challenging him to a competition. Alan won in poker, but he tells Sam that Sam will have to find the one thing he's best at. He does note there's one more thing Sam needs to know to force the Devil to accept the challenge, but he refuses to say what it is until he gets to Vatican City. Alan leaves and Sam and Andi figure he's telling the truth.
Nina visits Ben at the Work Bench and asks about his grandmother. He says that she's fine but that he lied and said he dumped Nina. Nina wants him to be honest with his grandmother and grow a backbone. Ben tells her that it's over and Nina walks away. However, she tells him that he broke her heart once and she forgave him, but not this time.
Sam and Andi have a drink at the bar and Sam admits that he's relieved that he's found a way out. He thanks her for her help and support and she kisses him. She apologizes and admits she just had to do it, but Sam says that it's fine. However, he wants to wait until he's out of his deal, once they hear back from Alan.
Alan is en route to Vatican City when the pilot announces they're stopping in Las Vegas for a maintenance check, and everyone will receive $100 in casino chips. The Devil, posing as a steward, is lurking on the plane.