|“||Damon: Look who got 27 across.
Bonnie: Huh, I wish. 27 across is a rock I am pushing up an endless mountain.
Damon: It's an old tongue twister. "Eddie turned top 40?" Eddie Vedder, Pearl Jam? "Yellow Ledbetter."
Bonnie: Are you messing with me?
Damon: No... You messing with me?
Bonnie: I didn't finish this.
Damon: Well, neither did I.
Bonnie: (stunned) There's someone else here.
— Damon and Bonnie in Prison World
A LONG WAY HOME — Knowing she needs to come to terms with the loss of Damon, Elena turns to Alaric to help her move on with her life. Enzo convinces Caroline to join him as he tracks down a lead to get Damon and Bonnie back, but Caroline is shocked when they make an unexpected detour and uncover what Stefan has been up to. Meanwhile, Matt worries about Jeremy who is spending time with Sarah, a mysterious girl who has recently arrived in Mystic Falls. Elsewhere, Tripp, leader of the community protection program, makes an interesting confession to Matt about his connection to the town. Lastly, with the Other Side destroyed and gone for good, Damon and Bonnie reluctantly bond together to uncover the mystery of where they are and how they are going to get back home.
Following the season five finale, Damon and Bonnie finds themselves in another dimension. It appears to be empty, but the destroyed buildings such as Mystic Grill and Gilbert House are not destroyed. The paper on the Gilbert lawn shows the date to be May 10, 1994.
Meanwhile, Jeremy hooked up with Sarah, the girl Elena fed on in the previous episode. Matt questions his choices, but Jeremy assures him that it's fine since Caroline compelled her to forget about the attack.
Elena decided to let Alaric erase her memories about Damon and throws away anything that reminds her of him. She also asks her friends not to mention him. She and Alaric begin going through her memories about Damon and altering them: the memory of their first meeting, first kiss, first dance, and makeout session, but can't seem to find the moment she fell in love with him.
Meanwhile, Caroline gets mad when she realizes that no one is trying to find a way to help Damon and Bonnie and goes to Enzo. The two go together to meet Stefan and find out that he has a girlfriend Ivy and join them for dinner. Over dinner, Enzo hints to Ivy about the supernatural world and Stefan's former life. Enzo stabs Stefan's hand which causes Caroline to compel Ivy. Stefan snaps Enzo's neck. Meanwhile, Caroline is on the phone with Alaric discussing the moment Elena realized she fell in love with Damon - which happened while she was with Stefan. Stefan overhears this and explains how he needed to leave the town and move on. Later, Enzo kills Ivy in front of Stefan for giving up on his brother.
Back in 1994, the next morning Bonnie finds her lost teddy bear Miss Cuddles at her house and Grams' grimoire at her house. Bonnie grabs the paper and realizes that the date is still the same, meaning that they're reliving the same day over and over again. The months pass and nothing seems to be happening. Bonnie is stuck solving the crossword and is missing one clue.
Meanwhile, Elena realizes that the moment she's looking for is the moment Damon gave her the necklace. When Alaric modified her memories, Elena concluded that Damon is "the monster that killed her brother".
Tripp informs Matt that the car Sarah came to Mystic Falls to was stolen. Matt tries to tell Jeremy about it and Sarah reveals that she's in town looking for her father. Matt calls Tripp back who thinks Sarah's story is a cover. Tripp also reveals that he's a part of the Fell Family and after the call he's seen bringing vampires to Mystic Falls to kill them.
In 1994, Damon compliments Bonnie on solving the final clue in the crossword. She tells him that she didn't solve it which means that they're not alone.
Special Guest Star
- Antagonists: Enzo and Tripp.
- Bonnie and Damon are stuck in a temporal time loop of the same day—May 10, 1994.
- Elena is seen packing up reminders of her relationship with Damon to be put in storage before Alaric compels her to forget their relationship. She's seen packing up photos, some of Damon's clothes, and a diary, among other things.
- Alaric compelled Elena to forget about her feelings for Damon, and without her memories of loving him, she now sees him only as Stefan's brother and a monster. Alaric was shocked by the hatred she showed of Damon right after her "signature" memory was altered, when the sound of Damon's name caused her to remember that he tried to kill Jeremy in The Return.
- Elena is surprised that Caroline is against her plan of having Alaric compel away her love for Damon, but Caroline reminds her that they're following a lead to bring back Damon and Bonnie, and worries that if they're successful, Elena being compelled to forget her relationship with Damon will make things awkward and confusing for everyone. Elena assures Caroline that Alaric can compel her to remember her altered memories if Damon does end up coming back.
- However, this "failsafe" ends up not working out (at least not in the way Elena originally thought), because Alaric is thrown over the anti-magic barrier in The More You Ignore Me, The Closer I Get and is returned to being a human before he is able to return Elena's memories with compulsion.
- Tyler, Stefan, Matt, Alaric, and the reluctant Jeremy and Caroline all agree to keep the fact that Alaric compelled away Elena's memories of loving Damon a secret from her.
- Enzo demonstrates that he has a soft spot for Caroline during his fight with Stefan.
- Believing Stefan is being selfish by giving up on his brother and wanting to give him payback for hurting Caroline, Enzo snaps Stefan's girlfriend Ivy's neck and promises that he will deliver on Damon's old promise for an 'eternity of misery' himself.
- Sarah reveals to Matt and Jeremy that she is in Mystic Falls to look for her father.
- Tripp reveals he is a member of the Fell Family, one of the Founding Families of Mystic Falls. He is also shown to have at least a little knowledge of the anti-magic spell over Mystic Falls, because he uses it to kill vampires that he finds lurking around the borders.
- Tripp reveals that he grew up with Elena's adoptive father/biological uncle Grayson Gilbert before his mother divorced his father and left Mystic Falls. He tells Matt that the name Tripp is a nickname, that his real name is Thomas Vincent Fell III, and that he took his mother's maiden name, Cooke, so he wouldn't be known as Tripp Fell.
- Tyler and Luke don't appear in this episode, but they were both mentioned by Elena.
- Abby and Grayson Gilbert were mentioned in this episode by Jeremy and Tripp, respectively.
- Bonnie and Damon discover that they're not alone in the "Otherworldly Time Dimension".
- Matt learns that Sarah stole the car she used to get to Mystic Falls, and as a result of that and the fact that Sarah was attacked by Elena, Matt decides he can't allow Sarah to stay at the Lockwood Mansion anymore.
- Bonnie goes into her own home in the 1994-world she and Damon are in, where she finds Ms. Cuddles, a teddy bear she lost when she was nine years old. She also goes into her Grams' house and retrieves her grimoire in hopes that she can use it to reactivate her magic so they can finally leave the dimension and go home to their loved ones, as she was sure that Grams sent them to their mysterious dimension knowing that Bonnie would be able to get them out.
- It was later revealed in The Day I Tried To Live that Bonnie didn't actually lose her bear as a child—Caroline stole it after she and Bonnie got in a fight, and because she didn't want her mother to find out that she stole it, she ran out into the woods and buried Ms. Cuddles there. Caroline would later go back to the woods with Stefan to dig her up in the same episode.
- Ivy - Broken neck; killed by Lorenzo St. John
- Unnamed Vampires - Purification and burned in sunlight; killed by Tripp Cooke
- Enzo was last seen in Home.
- Katherine was mentioned. She was last seen in Gone Girl.
- Abby Bennett Wilson was mentioned. She was last seen in A View to a Kill.
- Grayson Gilbert was mentioned. He was last seen via flashbacks in Fifty Shades of Grayson.
- Mystic Falls, Virginia
- Savannah, Georgia
- McKinley, Virginia
- 1994 Prison World
- Unknown town
- Hotel Albert
Behind the Scenes
- This episode had 1.67 million viewers in the USA, which is 0.14 million less than the previous episode.
- Hashtag during the airing is #WhenElenaKnew
- "Yellow Ledbetter" is a song by Pearl Jam, released in 1992 as a B-side to the single "Jeremy". In 1994, it reached 21 and 26 on the Billboard Mainstream Rock Tracks chart and Modern Rock Tracks chart, respectively.
- Caroline (to Elena): "Yeah, but we are literally chasing a lead. W-what if we find something out? Yeah, you know what if Damon returns home and everything returns back to normal? And you're just sitting there all confused and weird?"
- Elena (to Caroline): "But what? Go ahead, Caroline say what you need to say. I don't want to...pressure you into agreeing."
- Caroline (to Elena): "I--don't know what to say, I was actually trying to think of what Bonnie would say."
- Elena (to Caroline): "Look, I think it's great that you still have hope, I really do but--for my own survival I need to let him go."
- Caroline (to Elena): "Well, then go on with your what-would-Bonnie-Bennett-do plan. I'll make bumper stickers."
- Elena (to Jeremy): "It's been four months. It's time to let go."
- Jeremy (to Elena): "Are you going to erase Bonnie from your head too?"
- Elena: "Missing Bonnie, makes me sad, Jer. Missing Damon makes me dangerous."
- Alaric (to Elena): "I am supernaturally rewiring three years of your memories. If it were that easy, It wouldn't be so terrifying."
- Enzo: (to Stefan): "Stefan! You are a hard man to track down."
- Enzo: (to Stefan): "Got any bourbon?"
- Enzo: (to Stefan): "What kind of coward gives up on his own brother?"
- Stefan (to Enzo) "You don't know what you're talking about."
- Bonnie (to Damon): "What happened?"
- Enzo: (to Stefan): "Perhaps this will clear it all up."
- Ivy: "OH MY GOD!"
- Caroline: "ENZO!"
- Stefan: "What the hell is wrong with you?"