THE ROARING TWENTIES - Klaus and Stefan arrive in Chicago, where Stefan is reunited with a vampire who hasn't quite moved on from her interest in him decades earlier. In a flashback to Chicago in the 1920's, Stefan comes face-to-face with a shocking chapter from his wild past. After Damon gets a tip on Stefan and Klaus’s whereabouts from an unexpected source, he and Elena follow their trail. Back in Mystic Falls, Tyler is concerned about Caroline and turns to Sheriff Forbes for help.
|Damon gets a call from Katherine who is seen standing in a telephone booth. She knows where Klaus and Stefan are. She tells Damon that Klaus' hybrid's didn't work as they were expected to. Stefan and Klaus arrive in Chicago, the scene of Stefan's good old ripper days.
Flashback to the 1920s: In the middle of prohibition, Stefan is draining a young woman in the backseat of a car. He goes into a speakeasy where a woman named Gloria is singing. Stefan eyes a blonde woman who knows who he is. She kisses him and approves of the blood on his lips - a fellow vampire. Back in the present, Klaus announces they're going to see his favorite witch for help with his hybrid problem. Elena wakes up in her bed to find Damon next to her. He tells her Stefan is in Chicago.
In the dungeon, Caroline calls for her dad. A mist comes in and makes her choke. Bill comes in and tells her he's sorry "this happened to her." He wants to know how they walk in the sunlight. She nods to her ring. He takes it off and studies it, then throws it on the ground.
He tells her the dungeon where he's holding her used to be used on vampire's. Vervain in the ventilation, reinforced steel chair and a window with steel blinds. He taunts her with a bag of blood, saying it's how he's going to fix her. He opens the window blinds, burning her with sunlight.
On the road, Damon gives Elena Stefan's diary. She refuses to read his private thoughts and thinks she's already seen him at his darkest and can handle it. Damon drives and reads. Stefan writes he wakes up covered in stranger's blood with strange women. Elena reads on.
Flashback to the 20s: the blonde woman shushes Stefan and his friends so she can hear the singer. Stefan sarcastically asks her if they are offending her. She replies that it would take a lot more from a baby face like him to offend her. As she's walking away, Stefan asks her to tell him her name. She tells him when he earns it, and to do Gloria a favor and stick a sock in it.
In the present, Stefan and Klaus return to the speakeasy where they find Gloria, who is older, but not dead like she should be nearly 100 years later. She's a very powerful witch. Klaus sends Stefan away, but he listens to them talk. Gloria says to find out what went wrong with the curse they'd have to contact the witch who made the spell, who is very dead. She'll need help to contact her. "Bring me Rebekah," Gloria says.
Stefan finds a photo behind the bar. It's him with Klaus, but he has no memory of it. Tyler goes to see Sheriff Forbes. Caroline screams in pain as her dad repeatedly burns her with sunlight. She swears she doesn't hurt anyone. He says if she could handle it, she wouldn't react to the bag of blood. He shows it to her again. She fangs out. He's trying to condition her to associate vampirism with pain, so she'll learn to repress it. She tells him he can't change who she is. He burns her some more.
Damon and Elena visit Stefan's old Chicago apartment. Damon goes to the secret closet, which looks like it's full of moonshine. Elena sees the list of names. There are hundreds. Damon says Stefan was a "cocky ripper douche" back then. He kept his distance. He leaves her to go look for Stefan, telling her to come up with a plan.
At the speakeasy, Stefan is upset he doesn't remember that he knew Klaus. Klaus says at first he hated him. Flashback to the 20s: Stefan and the blonde share a woman, drinking from opposite sides of her neck. The two vampires start making out. She has an old necklace, the same one Elena wears in the present. She says it was from a witch. They're interrupted by her brother, Klaus.
In the present, Stefan processes he knew another original vampire. In a warehouse, Klaus opens up a coffin. There's his sister, Rebekah, preserved with a dagger through her chest. Stefan doesn't remember her. Klaus warns she has a worse temper than him. He removes the dagger.
Flashback to the 20s: Klaus quizzes Stefan on why he's worthy of his sister, an original. Klaus killed most of his family, but not Rebekah, after she chose his side. They're interrupted by a man demanding to see his wife. Stefan calls over one of the dancers, then compels him to stay put as he slices her wrist and lets the blood drip into a glass. He asks the man's name, then tells the man, Liam Grant, to drink.
In the present, Klaus tells Stefan he was his biggest fan. Klaus compels the warehouse security guard to direct Rebekah to Gloria's, then let her feed on him til he dies. Klaus tells Stefan he entrusted him with one of his biggest secrets and he's going to prove it. They're going to his old apartment. Damon pays Gloria a visit. She says Stefan's with Klaus and will be back in later tonight after they run an errand for her. She won't tell him what.
Elena reads Stefan's journal, about Lexi detoxing him. Elena hears Klaus and Stefan coming. In the hall, they see the door busted in. Elena hides in the secret compartment. Klaus tells Stefan he asked for Liam Grant's name then told him his secret, part of his ritual. In the small room, Elena sees Liam Grant's name on the wall. Stefan remembers he wrote down the names to relive the kill, over and over again. Klaus opens the secret door and holds it open for Stefan to walk inside. Elena has nowhere to hide, but is around the corner where Klaus can't see her. Stefan looks right at her, then announces to Klaus: "Look what I found."
But he grabs a bottle of single malt scotch and off they go. Damon returns with clothes for Elena. She called him an hour ago. He says he had that long to process what a bad idea it was to leave her alone and move on. He checks if she's okay. He says he knows where they'll be later, but wants to make sure she can deal with Stefan while he distracts Klaus, because he won't have long before Klaus rips his heart out. Klaus and Stefan return to Gloria's. Klaus says Stefan used to want to be his wingman.
Flashback to the 20s: Stefan tells Klaus that his family wants him dead because they are jealous that they can never be what he is. Klaus calls himself an abomination, Stefan corrects him and calls him a king. They drink up at the bar. Klaus warns Stefan about his sister and not to do anything stupid when she leaves him. They toast friendship.
Back in the dungeon, Caroline is exhausted from being scorched. She tells her dad she doesn't need to be fixed. He puts the blood in front of her again and makes her fight the urge. She tells him she's starving. He says he has to fix her so he doesn't have to kill her. The sun has gone down,so he promises to try again tomorrow.
He leaves and locks the door behind him. He looks up to see Liz pointing a gun in his face. Caroline hears Bill plead with Liz to let him proceed because they love her. Liz calls for Tyler. She fires a warning shot at Bill when he resists. Tyler goes in and releases Caroline, putting her ring back on her finger. He carries her out of the dungeon. Stefan and Klaus drink up at Gloria's.
Flashback to the 20s: Stefan dances with Rebekah, when suddenly Klaus senses something. The police bust in and start shooting the place up. Stefan and Rebekah hide behind the bar and she sees they're using wooden bullets. "That means he's here," she says and they run. She drops her necklace on the way out. Klaus compels Stefan to forget he ever knew them until he says otherwise, thanking him for reminding him what it was like to have a brother.
In the present, Stefan asks who Klaus was running from. Damon comes in and signals Stefan, who excuses himself. Outside, Stefan tells Damon that Gloria is seconds away from figuring out the doppelgänger isn't dead and that's why Klaus can't make hybrids. It's too late to send Elena home, she's at the speakeasy. Damon sits down with Klaus. Klaus promised Stefan he wouldn't kill Damon. Klaus wonders how long he has to honor that.
Outside, Elena hugs Stefan and asks him to come home. We see she has a syringe in her hand and is about to stab it into his back with vervain. But he catches her and knocks it away, asking how many times he has to tell her he doesn't want to come home. Inside, Klaus has lifted Damon off the floor by his neck and is stabbing him with a cocktail umbrella. Damon offers himself as a partner in crime instead of Stefan. Klaus throws him across the room and is about to stake him when Gloria ignites the stake and tells him to take it outside. Klaus promises when he's done with Stefan, he won't want to come back.
Outside, Stefan explains as soon as Klaus figures out Elena's alive, he'll know why he hasn't been able to make hybrids. He says if he goes with her it won't be the same, he's killed innocent people. He says it took him 30 years to pull himself together the first time. She doesn't have that long to wait. He says it's done. "I don't want to see you, I don't want to be with you, I just want you to go," he says and walks away. Damon rejoins Elena in the car. She just wants to leave.
Liz feeds Caroline bags of blood in bed back home. Liz tries to explain her dad has long held beliefs. He'll come around. Tyler asks if now would be a bad time to give her crap for sneaking out on him. He climbs into bed with her and holds onto her. She sobs her dad hates her.
Klaus returns to the warehouse to find his sister's coffin empty and the guard drained. Suddenly she's on him in a flash and stakes him through the chest, calling him Nick and telling him to go to hell. Flashback to the 20s: Klaus tells Rebekah they have to go or they'll be caught. She says she doesn't want to run anymore, she wants to be with Stefan. He tells her to choose between him or Stefan. She says goodbye. He stakes her.
In the present, Klaus calmly removes the knife from his chest, unhurt. He forgives her, saying he understands she's upset. Klaus calls in Stefan, then tells him he can remember. All of Stefan's memories of Rebekah and Klaus come back. He remembers they were friends. Klaus tells Rebekah that Gloria needs something from her. She realizes her necklace is gone.
Damon talks to Katherine in a phone booth again, saying she was right about Chicago. She won't tell him where she is now. Flashback again, to police busting into the speakeasy. Katherine is there and sees the necklace. Stefan picks it up. A man shows him sketches of Klaus and Rebekah. Stefan says he doesn't know them. Katherine leaves the phone booth. We see her in Chicago.
- Antagonists: Niklaus Mikaelson (present) and Stefan Salvatore (past).
- This episode confirms the existence of a member of the Original Family who is female (Rebekah).
- Rebekah was one of the last Originals to be neutralized by Klaus before the present day.
- This episode includes Damon and Elena's third road-trip.
- The necklace that Stefan gave Elena was revealed to have belonged to Rebekah, and was given to her by the Original Witch.
- Stefan discovers that Klaus and Rebekah were previously running from someone. He correctly deduced the same thing about Katherine in the episode Memory Lane.
- This is the first flashback episode of Season Three and is the first Klaus-centric flashback since Season Two's Klaus.
- This is the first episode of the season where a character voices diary entries.
- This is the first appearance of Rebekah and Mikael in the series.
- Mikael's name would later be revealed in Disturbing Behavior.
- This is Paul Wesley's favorite episode. 
- As of this episode, Caroline is tied with Jeremy for the second most appearances behind the three leads.
- Bonnie, Matt, Jeremy and Alaric do not appear in this episode. This is the first episode (this season) not to feature Matt, Jeremy and Alaric.
- This is the first episode of Season Three to feature Katherine.
- Klaus confirmed that the Original Witch was the one who created The Hybrid Curse.
- Katherine and Elizabeth Forbes were both last seen in As I Lay Dying.
- Damon mentions Katherine's escape attempt from Klaus, which happened in As I Lay Dying after she gave Damon the antidote to his werewolf bite. She had been on the run until this point.
- Lexi was mentioned in this episode. She was first seen in 162 Candles (when she was killed by Damon), but last appeared in The Dinner Party via flashback.
- Andie Star was mentioned. She was last seen in The Birthday (when she died after Stefan compelled her to jump off of a scaffolding).
- Klaus mentions the sacrifice ritual to Gloria, which was performed in The Sun Also Rises.
- Bill Forbes was first seen in The Hybrid.
- The End of the Affair is a 1999 film with Ralph Fiennes, which also features two men who are in love with the same woman. One of the most famous quotes of this movie is "Love does not end just because I do not see you" - which echoes Elena's feelings for Stefan.
- Elena asks Damon if he was paving the way for "Woman's Liberation." He would be a little late for that, because women's right to vote was added to the US constitution in 1920.
- Stefan hid his alcohol - he had to, because Prohibition was in effect. From 1920 until 1932 the manufacture, sale and transportation of intoxicating liquors was outlawed. During this time even the average citizen broke the law, and gangsters took advantage of the demand for illegal alcohol to rise to power.
- Damon mentions Daisy Buchanan, who is a character from The Great Gatsby, by F. Scott Fitzgerald. The book is set in 1922, just as the flashback sequences. She is torn between her love for her husband, Tom, and Gatsby. In a previous conversation, Stefan had told Elena this was one of his favorite books.
- "Come out, come out, wherever you are " is a phrase frequently used in fiction. It's in a Frank Sinatra song, mentioned in Cape Fear, Queen of the Damned, The Wizard of Oz, Hell Raiser, Shrek, and The Shining, among 119 others.
- When Katherine leaves the phone booth, a bus goes by with a sign for "Chicago's Best Jazz." Chicago played an important role in the evolution of Jazz during the 1920's.
Behind the Scenes
- This episode had about 2.75 million viewers in the USA.
- Elena reads from Stefan's diary:
- April 1922: "Lexi found me last night. Dragged me off the train tracks. She thinks she can make me care again."
- June 1924 (sighs): "Lexi's driving me crazy. More animal blood, more misery."
- 1935: "Cravings are there, but it's easier. Lexi's on to her next project: (He chuckles) Getting me to laugh."
- Damon (to Klaus): "What can I say? I'm a thrill seeker."
- Damon (to Klaus): "You want a partner in crime? Forget Stefan. I'm so much more fun."
- Rebekah (to Stefan in 1920): "Careful Mr Salvatore, you’re still wearing your date. She’s lovely."
- Damon: "Rise and shine, sleepy head."
- Elena: "What are you doing? Get out!"
- Damon: "You know you were dreaming about me. Explains the drool."
- Elena: "Oh my god. 6 AM? Seriously? You have nothing better to do at 6 AM!?"
- Damon: "It came to me in a dream, I was naked, you would have loved it."
- Damon: "... It would suck if your last memento of Stefan was that crappy old necklace."
- Elena: "It's an antique, Damon. Like you."
- Rebekah: "Sorry to crash the fun boys, but some of us actually came here to hear the music, not you."
- Stefan: "I’m so sorry sweetheart, are we offending you?"
- Rebekah: "It takes a lot more than a baby face like this to offend me."
- Stefan: "Hey, are you even gonna tell me your name?"
- Rebekah: "Sure, when you earn it."
- Damon: "I'm shocked. Stefan's not a virgin?!"
- Damon (to Elena): "I had an hour to realize it was a bad idea to leave you here— process it —and move on."