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.
- 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.
- Mystic Falls, Virginia
- Chicago, Illinois
- Liam Grant - killed by Stefan
- Unnamed woman - killed by Stefan
- Unnamed security guard - killed by Rebekah
- 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.
- Klaus calls Damon Riff Raff, who is a character from a cult musical The Rocky Horror Picture Show.
- The first song in the episode is named St. James Infirmary. St. James Infirmary will be seen on The Originals.
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."