|“|| Elena: When I look into your eyes, I just...|
Damon: What? What are you feeling?
Elena: I feel like I'm looking at a stranger.
MEMORIES FROM ANOTHER TIME — When the past comes back to haunt her, Elena is forced to face her problems head on. After a night at the annual Whitmore Medical Center Fundraiser, Jo opens up to Alaric about her own tragic past. Meanwhile Stefan, Matt and Enzo resort to extreme measures when Tripp withholds information about his vampire-killing operation, and Caroline is in a race against the clock when Sheriff Forbes gets caught in the middle of a dangerous plan. Elsewhere, Tyler and Liv grow closer, and Damon stumbles upon a startling clue that renews his hope. Bonnie also appears.
Special Guest Star
- Antagonists: Tripp Cooke (and henchmen) and Kai.
- This episode marks the 100th appearance of Caroline Forbes on the show.
- Damon, believing that Kai killed Bonnie after he was sent back to the living world, lied to everyone about Bonnie being in the prison world with him to spare their feelings. However, he found Ms. Cuddles at the Salvatore crypt in Mystic Falls Cemetery, which revealed to him that Bonnie is still alive and had sent her bear through the portal to tell him so.
- Kai patched up the arrow wound he gave Bonnie in order to help convince her to send them both back to the living world.
- As of this episode, Bonnie Bennett overtakes Jeremy for a total number of appearances on the series. Before this point, Jeremy had the second most total appearances after Caroline for three seasons straight outside the main three characters Elena, Damon, and Stefan.
- The title may refer to the first time you meet someone, fell in love, first date or had sex with someone, which is fitting considering Elena's lack of memories of loving Damon.
- Liam considers him and Elena going to the Whitmore Fundraiser together a date even though Elena reminds him that their attendance is mandatory. She looks slightly guilty after he leaves because he kissed her.
- Damon compels Liam to get Elena some Chardonnay, which Damon knows she doesn't like, so he can talk to her alone.
- Liz was captured by Tripp's team and they held her captive until Tripp was released.
- Tripp is killed by Enzo.
- Damon goes over some of his worst moments with Elena while talking to Alaric in his room at the Whitmore Medical Center. Alaric reminds Damon of the time he killed Jeremy in The Return after Elena told him she could never love him.
- When Elena and Damon shared a dance at Whitmore Medical Center Fundraiser, the song "Belong" by Cary Brothers was played in the background. It's the same song featured in Graduation during Elena's confession of love.
- After being forced by Kai to rebuild the Ascendant, Bonnie seals her magic inside her bear and uses the passing of the eclipse to send it back to the present where it is found by Damon. This leaves both Bonnie and Kai still trapped in the time loop with no magic to allow them to break free.
- It is revealed in this episode that witches can "store" their magic into an object by binding their power to it for safe-keeping.. This has so far only done by Jo and Bonnie.
- Damon tells Elena that he knew she was the girl for him when got into his car, in Home, to go with him to set off the explosion at the Mystic Grill, because it was then that he knew she was as crazy as he is.
- Elena crosses the border for a few moments in a desperate attempt to regain her memories of loving Damon, but when she starts coughing up water from the anti-magic spell, Damon pulls her back and tells her that her safety is what matters to him most. This method was also used by Sarah and Tripp to inadvertently strip away their compulsion.
- Elena has flashes of her relationship with Damon, but retains only part of her memory of the last night she and Damon had together before she went off to Whitmore when they went to the docks at the lake to watch a meteor shower and got caught in a heavy rainstorm. When Elena asks him what happened after the rain started, he lies about the rest of the memory by saying that they were cold and miserable and left early. However, in reality, Elena had made him promise that their relationship would be forever and then passionately kissed him in the pouring rain.
- Damon decides to let Elena go by telling her that she can live this new happy life without him but tells her that he still loves her.
- Jo revealed a tragic history of her past in which she was stabbed and lost her spleen as a young adult, which indicated that she's Kai's sister.
- Liam confronts Elena about the girl who played "Lady Whitmore" at the corn maze that Elena saved with her blood. He tells Elena that the girl got into Whitmore on a tennis scholarship but injured her shoulder, which required regular surgical procedures to treat so she could retain her scholarship. However, since the night at the corn maze, her shoulder has been completely healed as well. Just before Liam leaves, he says that Elena is both a liar and a girl with secrets, and insists that he's going to figure out what those secrets are.
- Bonnie killed Kai by stabbing him in the neck in order to buy herself some time to rebuild the Ascendant and go home by herself. However, he woke up too quickly and stopped her before she could leave, instead forcing her to take him with her.
- Bonnie's teddy bear Ms. Cuddles is similar to Elena's teddy bear which can be seen in Elena's bedroom in earlier seasons.
- Tripp - slit throat (first time), the Magic Purification Spell (second time), killed by Enzo. (as a human/vampire)
- Kai - killed by Bonnie Bennett, later resurrected because of the metaphysical laws of the 1994 Prison World.
- McKinley, Virginia
- Mystic Falls, Virginia
- 1994 Prison World
- Tyler, Liv, Kai, Bonnie, and Liam were last seen in The World Has Turned and Left Me Here.
- Whitmore Hospital's Fundraiser Party is the second party at Whitmore College that Elena and Damon have attended but not as a couple as they were in Monster's Ball when they went as a couple to the Historical Ball in Season Five.
- This is the second time that Damon has let Elena go, the first time was in Rescue Me.
- This is the second episode to feature a rain scene between Elena and Damon.
- Tripp is the second member of the Fell Family to be turned into a vampire.
- Damon mentions turning Vicki Donovan into a vampire. He turned Vicki in Lost Girls, and she was last seen as a ghost in Resident Evil.
- Damon alludes to Amber Bradley, as Stefan had a bloodlust issue in the episode, Miss Mystic Falls.
- Damon pours bourbon on Honoria Fell's grave in a symbolic gesture, but drunkenly calls her "Horatio" instead.
Behind the Scenes
- This episode had 1.54 viewers in the USA, which is 0.05 million less than the previous episode.
- Hashtag during the airing is #DelenaMemoryLane