In the past, little Neal is bitten by a poisonous snake. Rumplestiltskin and Mila must pay 100 gold pieces for the cure to save him. Mila tells Rumplestiltskin to kill the man with the cure and steal it since they have no hope of getting 100 gold pieces. While waiting for Rumplestiltskin at a bar, Killian saves her from a drunken bully.
Rumplestiltskin can’t kill the man for the cure but he gives it to him anyway but tells him there is a terrible price to pay if he’s willing to make a deal. Rumplestiltskin comes home with the cure. He tells Mila he promised the man their second born child instead of killing him. He says they just have to make sure they never have one. Mila is devastated. Later, as the Dark One, Rumplestiltskin kills the man to void the contract.
Hades wants Hook to pick three of his friends to stay in the Underworld. When he refuses, he threatens to throw him into the river of lost souls as he sends him to Solitary.
Rumplestiltskin offers to help Emma get into Hades lair by getting borrowing Mila’s aura to fool his protection spell. Mila helps them get down to the River of Lost Souls but Rumplestiltskin refuses to leave the bought. Emma goes to find Killian while Mila stays to make sure Rumplestiltskin doesn’t steal the boat.
Hades offers Rumplestiltskin a deal. He wants Rumplestiltskin to sink the boat so his friends stay in the Underworld and he’ll send him back home to Belle.
Emma rescues Killian before he ends up on the river. Rumplestiltskin throws Mila into the River of Lost Souls, burns the boat and blames Hades when Emma and Killian arrive.
Cruella tells Regina that the headstones have meaning. Upright means they are in the Underworld. Tipped over means they’ve moved onto a better place and cracked means they’re somewhere much worse. Regina looks for Daniel’s headstone. It’s tipped, meaning he has moved on and is happy.
When Regina and Snow come across an injured horse in the Underworld, Regina uses magic to cure it. She’s shocked that she can use magic here. Later, Regina tries to split Emma’s heart to give to Killian but she can’t get to it. They find three new headstones in the cemetery: Regina Mills, Snow White, and Emma Swan.
Hades refuses to send Rumplestiltskin back home yet. He realizes that Belle is pregnant. The man Rumplestiltskin made the deal with long ago to give away his second child is in the Underworld and Hades has had it signed over to him.