The episode begins and Damon wakes up Elena is still there, in her underwear. He's happy. Caroline wants to go to Tyler for advice on the sire bond. Tyler, Hayley and Kim, who broke her bond, oversee Adrian's attempts to break the sire bond to Klaus. At his house, Damon tries to convince Elena to wait to tell Stefan about them, just for one day. She agrees. At school, Elena invites Caroline and Bonnie over to the Salvatores. Bonnie has some new small spells from Shane she wants to try. Shane comes back to his office to find Hayley rooting through his stuff. Once she brings him 12 unsired hybrids, he'll give her information on her biological parents.
She has 11, not including Tyler, whom she's trying to keep out of it. Caroline calls Stefan, explaining how the hybrid bond works. But there's no vampire equivalent. Stefan comes home to find Damon rooting through old papers. He tells Stefan he was right about Elena. Damon reminds him about New Orleans in 1942, and Charlotte. Flash back to 1942 Charlotte asked him to turn her, so he obliged. In a club, she picked out the singer she wanted to have for dinner. Damon went to talk to the singer, telling Charlotte to "show no mercy" if anyone touched his drink. When a sailor knocked it over moments later, she snapped his neck in a room full of people. She was sired to Damon. Back in the present he is found a witch named Valerie La Marche to help him break the sire bond.
In New Orleans, Stefan tells Damon the sire bond is responsible for Elena's feelings for him. In 1942 Lexie walks Stefan through the apology he's going to give Damon. Stefan finds him at a New Orleans' bar and says he wants to bury the hatchet. Stefan's about to ship out to war and shall be driving an ambulance in Egypt. Damon talks about joining him. When Stefan goes to get them a round, Lexie tells Damon he can't go with Stefan to war. He needs a balanced perspective of war. Charlotte brings a bleeding woman in for Damon to feed on. Stefan starts to feel his old ripper urges and has to run off. Lexie tells Damon that Charlotte is better off without him, too. Back in the present, Damon doesn't know where to find the witch, so they decide to find Charlotte.
Damon left her on a street corner after telling her to count every brick in New Orleans. Stefan wonders how literal the bond is. Back in Mystic Falls, Hayley tries to convince Tyler to pressure Adrian into finishing breaking the sire bond. When he leaves, Kim tells Adrian they're going to go pick a fight. In New Orleans Charlotte isn't on the corner where Damon left her. They debate what to tell Elena. He leaves to get a drink. Walking alone down the street, he hears something and someone jumps on him. Stefan comes over and pulls her off. It's Charlotte. She kisses him. "I always knew you'd come back for me. I must have counted literally every brick on every building in all New Orleans," she says. On the plus side, Damon points out, she knows New Orleans better than anyone.
In New Orleans Damon and Stefan go into Nandi's shop and ask directly about a spell to break a sire bond. She says Valerie was her great-grandmother. He tells her Val had a Grimoire with a spell like that in it. In 1942 as a little girl writes lessons in the other room, Val tells Damon that the spell uses dark magic and the sacrifice of 12 humans. Back in the present Nandi says all of Val's Grimoires and spells were lost in Katrina. She says she doesn't practice. At the Salvatores', Kim and Adrian are standing on the doorstep. They rush in. Kim grabs Caroline and Adrian grabs Elena. Bonnie starts to use magic, but Kim reminds Bonnie that one bite from a hybrid could kill Caroline. They grab Caroline and leave.
Out on the street, Damon says he killed 12 people to try to break the sire back in 1942 and he'd do it again. In the woods in Mystic Falls with Tyler, Elena looks for Caroline. Tyler says that even if Adrian is still sired to Klaus, it doesn't mean he likes him. They hear Caroline yell in the distance. Damon returns to Nandi's shop, busting her for being Val's daughter. Flash back to the girl in 1942 writing out her name as Nandi. She's 80 but doesn't look a day over 50, which means she's practicing. When Damon steps toward her, she uses magic to immobilize him. Stefan steps out, saying they don't want trouble. Nandi says there was no spell.
Her mother made up the need for sacrifice so she could access magic so dark it's called "expression". A sire bond can't be broken with magic. A vampire only develops the bond when she has human feelings for her sire before she turns. Vampirisim only heightens those emotions. To free her, Damon has to tell her to live her life without him and never think of him again and then leave her. Back in Mystic Falls, Kim tortures Caroline in the barn, to "show Tyler who's in charge". When Tyler comes in and tells her to stop and says they're on the same team, she says they're not. Tyler and Elena are quickly surrounded by the other hybrids. When Kim picks up a stake to use on Caroline, Elena suggests they torture her instead if they want to upset Klaus. When Kim goes to grab Elena, Tyler grabs Kim and rams his hand through her chest, threatening to rip her heart out. He addresses his fellow hybrids. "Kim put you all at risk today, but I'm not going to hurt her, I'm not Klaus.
I don't kill and torture my own friends to get what I want. Now we broke the sire bond. But if you want to be free, we have to work together. No one can step out of line. Now you're either with me, or against me. Submit. Submit or you die" he tells Kim. She apologizes and he lets her live. The other hybrids kneel before him. Back in New Orleans, Damon tells Charlotte she has to forget about him. Damon meets Stefan on the street. Stefan immediately questions whether he'll be able to do the same for Elena, pointing out Damon's not known for his selflessness. "Yea well, one of these days you're going to realize you don't know me half as well as you think" Damon says. In 1942 Damon arrives at the train station in uniform, ready to ship out.
Lexie is there. She tells him again he can't go overseas with Stefan. She knows he just killed 12 people. If Stefan finds out that Damon can do it without guilt, he'll become a ripper all over again. Damon says he's been on his own since 1919 and needs his little brother again. She says it'll destroy Stefan and for once, Damon has to put someone else first and let him go. Damon sees Stefan waiting for him by the train tracks, but he picks up his bag and leaves. Back in the present Damon tells Stefan what he did in 1942. Stefan says that even if Elena never feels the same way about him again, at least it'll be her choice.
Damon knows what he has to do. At the Salvatores' house in the morning, Elena notes to Caroline that whatever Shane's teaching her seems to be working. He calls it "expression," Bonnie says. In Shane's office, Hayley tells him Adrian broke his bond. She asks where her parents are. They're dead. She warns him he just picked a fight with a werewolf, but he says just because they're dead, doesn't mean she can't see them again. Stefan tells Caroline he feels bad for Damon, knowing he really does love Elena. Stefan thinks he'll do what he says. Stefan trusts Damon because he thinks Damon loves her as much as he does. "He can't be selfish with her, not anymore" he says. Damon returns home to see Elena cleaning up.
He says they need to talk, and she says she knows she's sired to him. She tells him what Tyler said about the bond not affecting her feelings. She knows what he's about to do and asks him not to. He knows that he's not the guy who does the right thing, but he has to do the right thing by her. She takes his hand and holds onto his face and asks if it feels wrong. The episode ends at this point.