Crowley joins Jody Mills, who is at a bar to have a blind date. She thinks that his name is Roderick and they chat back and forth. Later, Crowley finally says that they both share loss. Jody remembers losing her son and husband, and Crowley takes her hand and says that he's lost someone as well. Jody breaks into tears and goes to the restroom to clean up. She takes some lipstick out of her purse, while at the bar, Crowley sets up a hex. In the restroom, Jody starts choking and coughs up blood. Meanwhile, Crowley gets a call and tells Dean that Jody will die in a minute. Dean tells him that it's over and offers to turn over the demon tablet if he gives them the angel tablet. Crowley agrees once they say that they surrender.
Later, Sam and Dean meet Kevin to get the second half of the tablet, which he buried beneath a sign with a devil on it. The brothers give Kevin a key to the Letters base and tell him to stay there, and Kevin assures them that they're doing the right thing.
In Houston, Castiel and Metatron watch a bartender sweeping up outside his bar. Castiel asks what God was like, and Metatron says he was pretty much like someone would expect. He assures Castiel that it was necessary to kill the nephilim, and the next person on the angel's list is the homeless man, Dwight Charles. Dwight is supposed to find love when Cupid shoots him in 24 hours. The second trial is taking Cupid's bow, and Castiel is relieved to know that there's no killing.
In Sioux Falls, Dean and Sam go to a junkyard to make the exchange with Crowley. Sam takes it out briefly to show it, and Crowley shows the angel tablet. The demon then rolls out the contract and Dean insists on reading the fine print. Sam says that he'll do it but Dean insists, and Crowley realizes things aren't good between them.
One of Naomi's angels, Nathaniel, comes to tell her that a freelancer has found Castiel in Houston. Nathaniel also tells his superior that Metatron is with him.
Dean finishes reading the contract while Crowley points out that they always lose because they're human. Sam steps forward, but Dean handcuffs Crowley. The demon discovers that he can't teleport away because they're demonic handcuffs. Crowley attacks Dean, who punches him back and takes the tablet. The brothers then explain that Crowley is the third trial.
Castiel and Metatron go into the bar and Castiel reads the personal advertisements. He figures that the sooner Dwight finds love, the faster Cupid will come. Dwight comes over and hints around suggesting that he is looking for love. Metatron hastily orders a drink, but Naomi and her men arrive and grab Metatron. Dwight grabs a shotgun and shoots one of them, but an angel teleports over and knocks him out. Metatron tells Castiel to back down, and the angels teleport away.
The Winchesters take Crowley to an abandoned church and Dean seals him within a devil's trap. He goes out to join Sam, who figures that they might actually win. They go over the ritual instructions and Sam figures that he has to give him an injection of his purified blood every hour for eight hours, and then feed him the rest. Dean points out that Sam's blood has to be purified and offers him some helpful tips on what he has to confess about. Sam goes into the church's confession booth and begins confessing.
Outside, Castiel teleports to Dean and asks for his help rescuing Metatron. The angel says that he's been working on the angel trials to shut down Heaven and Hell.
In Naomi's office, Naomi tells Metatron that they've never officially met. He remembers that the archangels wanted her to debrief him after God left, but the Scribe escaped. Before they begin, Naomi asks him why he let himself be captured, and what he's doing with Castiel. Metatron quotes the Bible and Naomi starts drilling into his head.
Castiel gives Dean a full explanation and insists that he can't fail. Dean doesn't want to leave Sam alone, but Sam overhears them and tells his brother to go. He assures Dean that he got it and figures that locking up the angels is a good thing. Dean tells Sam to finish it in eight hours whether he returns or not and then leaves with Castiel and the tablet. Sam goes inside and gives Crowley the first injection. Crowley smiles smugly, unaffected, while Sam's arms glow.
Castiel and Dean meet with Kevin and have him translate the angel tablet. He warns them that it will take him months to do it even if he wanted to, and Castiel grabs him and says that Kevin is a Prophet of the Lord until the day he ties. Kevin reluctantly goes to work while Castiel and Dean leave.
At the church, Sam gives Crowley the next injection. Crowley grabs his arm and bites him, and Sam walks outside. Once he's gone. Crowley spits out the blood and uses it to cast a spell summoning help.
Dean and Castiel return to the bar and Castiel goes looking for women to line up with Dwight. Dwight is happy to give them free drinks because he thinks Castiel saved his life. Dean wonders if Castiel is sure about locking himself in Heaven with the others angels, and reminds him that they want to kill him for what he did. Castiel admits that he'll probably die.
A deliverywoman, Gail, comes in and Dwight chats with her. He introduces her to one of the clients, Rod, and Gail touches both of them and leaves. Dwight and Rod start chatting and Castiel realizes that true love has struck.
Crowley continues taunting Sam as he continues giving injections. The church shakes and a crack spreads down the floor, breaking the devil's trap. Abaddon storms in and tells Crowley that she's the only one who came to get him. Sam goes for his gun but Abaddon telekinetically throws him through a window. However, when Crowley tells her to release him, she slaps him.
Gail comes out and finds Dean and Castiel waiting for her. She greets Castiel as "brother" and he tells her to hand over her bow. When the angel draws his knife, Dean tells him to try talking first.
Abaddon continues beating Crowley, who reminds her of what Sam is trying to do. He tries to grab Sam's gun but she easily casts it away, and then says that they're going to discuss regime change. When Crowley objects, she beats him again. However, Sam comes in and douses her with gasoline, and then sets her on fire. Abaddon's demon essence leaves her body and flies out the window.
Gail admits that she hasn't gone back to Heaven because everything there has been breaking down. Castiel says that he can fix it with time and Gail lets him cut the tattoo of her bow from her hand.
Naomi demands to know what Metatron is doing, and he explains that he suffers from eternal longing after God plucked him from obscurity. The archangels ran Metatron from his home and he plans to have his revenge. Naomi teleports away, and Metatron notices her drill on the nearby table.
Crowley admits that he's proud of Sam, who fills the devil's trap in again. The demon is shocked that Sam isn't more appreciative that he helped him. When Crowley starts quoting Girls
and begging for love, Sam realizes that the cure is taking effect. He draws more of his blood for the next treatment, and Crowley asks Sam what he confessed to earlier. The demon wonders where he starts to look for forgiveness. Sam holds up the syringe and says that they start with it, and Crowley bares his neck.
As Dean calls Kevin to find out what he can learn about the nephilim and Cupid's bow, Naomi appears and tells Castiel that Metatron is trying to break Heaven by expelling all of the angels and banishing them to Earth. Castiel doesn't believe it but Dean stops him. Naomi admits that they forgot their mission from God to protect mankind. She warns Dean that she saw in Metatron's head that Sam will die when he completes the trial. Naomi begs Castiel to stop the trials and promises to listen if he wants back in. She teleports away and Dean asks Kevin if Naomi was lying. Castiel is sure that she is, and Dean tells the angel to take him to Sam.
Sam prepares to perform the last part of the ritual.
Castiel teleports Dean outside the church and then says that he's going to fix his home. He teleports away and Dean runs in and tells Sam to stop.
In Heaven, Castiel discovers that Naomi is dead, the drill driven into her head. Metatron puts a blade to Castiel's throat and says that Castiel should have listened to her.
Dean tells his brother that Metatron lied, but Sam says that he's been expecting it all along.
Metatron straps Castiel to the chair and tells him not to worry about it. He scratches Castiel's throat and takes his essence, explaining that it's the last piece of his spell. Once he heals the wound, Metatron says that something will happen for both of them. He tells Castiel to have a good human life and then tell him the story when he dies and comes to Heaven, and teleports him to Earth.
Sam says that people will die if he doesn't finish the trails. He figures that Dean doesn't trust him, and says that he confessed to letting Dean down. Sam refuses to do it again and asks who Dean will turn to next time. Dean points out that he killed Benny because of Sam, and is willing to let all of the demons walk, and begs Sam to see that he will always come first. After a moment, Sam asks how he stops and Dean assures him that they'll figure it out together. He binds Sam's wound and hugs him, and Sam recovers for a moment... and then gasps in agony. Dean yells for Castiel and gets no response.
Castiel wakes up in a forest on Earth.
At the Letters' lair, all of the machinery starts up and alarms go off.
Castiel wakes up and walks through the forest, looking toward the sky.
Kevin finds a map of the world and sees red spots light up across the globe.
Dean sees lights dropping out of the sky and assumes that Castiel has succeeded. Angels drop out of the sky, slam into the ground, and keep going into Hell. Dean realizes that the angels have fallen.