|“|| Caroline: Don't let go, Mommy.|
Liz: I won't. Until you're ready.
Caroline: Don't let go, I'm not ready.
Liz: Yes, you are..
— Liz helping Caroline to learn to ride a bicycle when she was little
GOODBYE, MYSTIC FALLS — It’s Jeremy’s last day in Mystic Falls and Elena puts on a brave face as they reminisce about their past. Stefan and Caroline find themselves growing closer as they prepare Caroline’s family cabin for her mother to live out her final days. While packing up her office, Sheriff Forbes turns to Damon for help solving one of her remaining open cases involving Elena’s parents. Elsewhere, when a violent confrontation with Enzo leaves Jeremy wondering whether he should leave or not, Matt finds his own life on the line after Enzo lures him and Sarah Salvatore into his dangerous plan. Lastly, Caroline rushes to the hospital after learning her mother has taken a turn for the worse. Alaric also appears.
- Antagonist: Enzo.
- This episode marks Jeremy last appearance before Steven R. McQueen leaves the show. As far as anyone else knows, Jeremy is leaving for art school. However, unknown to anyone but Alaric, he has actually decided to be a full-time vampire hunter instead. Alaric sent him away with a cache of anti-vampire weapons and plans on sending him tips about potential vampire attacks around the US. At the end of the episode, Jeremy leaves for his first stop, which is Santa Fe, New Mexico, where several animal attacks have been reported.
- Before Jeremy leaves, Alaric tells him that if Elena finds out that he let him leave to hunt vampires, she'll kill them both.
- This episodes establishes the series' current timeline as 2013 with the mention that Jeremy started his freshman year in 2009. It is further established by the comment that Elena and Jeremy's parents died in the car accident almost four years ago.
- Elena proves that she can sneak up on Jeremy without him hearing her by using her vampire abilities.
- Elena gets high with her brother Jeremy before he leaves, or at least gets buzzed by smoking the joint that Damon gave him as a going away present. This is the first time Elena is seen smoking pot, because, like most of the vampires she knows, her "drug of choice" is alcohol.
- When Elena later goes to see Damon and the Sheriff, she doesn't appear to be inebriated any longer, implying that while vampires can technically get high, the effects of the drugs are shorter-lasting than they would be with a regular human. This fits in with canon, as it has also been established that vampires have much higher tolerances for alcohol because of their accelerated healing.
- Jeremy asks Elena if he can have her SUV, and argues that she could easily compel herself a better car. Though Elena initially rejects this proposal, she eventually agrees to ship her car to Santa Fe for him to drive.
- While they discussed this, they also go over each car that their family has destroyed over the course of their lives.
- Liz dies in this episode with Caroline, Stefan, Elena, Matt and Damon at her bedside. In order to be with her comatose mother in her last moments, Caroline enters her mind with Stefan's help and brings back her happiest memory with her mother: when she taught her to ride a bike without training wheels.
- Liz is the first recurring character to die a natural death in the series.
- Stefan taught Caroline how to use her vampire mind-control abilities to "get inside someone's head" by using a form of telepathy to induce a dream or vision. In this case, Caroline uses it to replay her favorite memory of her and her mother together.
- Caroline is the first vampire turned from Damon's bloodline to demonstrate this ability, as Elena has yet to be seen doing so.
- Liz spends her last day with Damon investigating cold cases, including one about Miranda and Grayson Gilbert. Liz was concerned that she had missed something in regards to the accident, because the night they died, Miranda left an urgent voicemail for Liz saying they needed to talk, and the fact that there were no skid marks on Wickery Bridge suggested something suspicious was going on. In addition to this evidence, Miranda and Grayson were shown to have luggage in their trunk, and the route through Wicker Bridge wasn't the most direct way to return to the Gilbert House. Because of these unanswered questions, Liz suspected foul play, and admitted to Damon that she never brought it up to Elena and Damon because they were still grieving.
- Liz and Damon eventually discover that the message was just a joke played by Miranda and Jenna, who had caught him smoking marijuana in his room that night and wanted to scare him into dropping the habit. The luggage was also explained to have been in the trunk because the family meant to take a surprise trip to their lake house, but a storm prevented them from going, and also why there were no skid marks on the bridge, as the bridge had poor drainage at the time, something only later fixed. Finally, the detour was explained to have been because a tree had fallen across the most direct route.
- After Damon confessed that he was supposed to give the eulogy at his mother's funeral and chickened out at the last minute due to nerves and an inability to write his speech, Liz asks Damon to give the eulogy at her funeral so he can make up for it.
- It is revealed out that the reason Damon was in town the night of the Gilbert car accident was because his mother died around that time, so he came to leave flowers on her grave, as he did every year when his humanity switch was on.
- Stefan and Caroline share a kiss for the first time in this episode while they are preparing the lake house.
- It is revealed that Alaric can no longer go to Mystic Falls out of fear that he could be recognized, since his death was very publicized and he was dead for two years before he was resurrected.
- Because of Enzo, Sarah learns that supernatural beings exist who can heal people with their blood and run very fast, as Enzo purposely hit Matt with his car to demonstrate these abilities to her just enough to make her curious to learn more. It's unclear if she knows about vampires, or the fact that Enzo is one.
- In The Downward Spiral, it was revealed that while Sarah did not right away assume that Enzo was a vampire after seeing Enzo heal Matt, she was still not impressed when Enzo revealed his identity to her, as Stefan had previously compelled her to not fear or be interested in vampires as a way to ensure her protection.
- Mystic Falls, Virginia
- Elizabeth Forbes - Complications from Stage 4 glioblastoma
- Grayson Gilbert and Miranda Sommers-Gilbert both died before the Pilot after their car accidentally ran off of Wickery Bridge and caused them to drown. They were both last seen in flashback in the Season Three finale The Departed.
- Alaric returns after being absent for two episodes.
- He was last seen in Woke Up With a Monster.
- Carol Lockwood is mentioned by Liz in the May 23, 2009 flashback. She was killed by Klaus in O Come, All Ye Faithful in Season Four.
- This is the third flashback to 2009 this season and the second to the night (May 23, 2009) Elena and Jeremy's parents died.
- This is also the sixth flashback episode this season.
- Jenna Sommers was mentioned. She was last seen as a hallucination in 500 Years of Solitude.
Behind the Scenes
- This episode had about 1.52 million viewers in the USA.
- This episode marks the final appearance of Steven R. McQueen as a series regular.
- "The original pitch was a bucket list, but she'd take a turn for the worse before she could do the last thing so Caroline would go into her mind and give her that last thing. Once we broke the investigative story line involving the parents and we realized the closure in that mystery put her to sleep we went this way. In the midst of all the pain and sadness, there is a beauty and peace to be found in your last moments and to send somebody off feeling like a character gave them that is really important." 
- Hashtag during the airing is #ByeJerBear
- "Stay" (full title: "Stay (I Missed You)") is a song by Lisa Loeb released as a single in 1994 and featured on the soundtrack for the movie Reality Bites.
- "Stay" is a thriller/drama movie released in 2005.